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{"id":33550,"date":"2020-07-22T08:05:11","date_gmt":"2020-07-22T00:05:11","guid":{"rendered":"\/\/www.gsbet888.com\/?p=33550"},"modified":"2020-07-20T09:58:33","modified_gmt":"2020-07-20T01:58:33","slug":"heck-matsuda%e5%8f%8d%e5%ba%94%ef%bc%88%e4%b8%89%ef%bc%89","status":"publish","type":"post","link":"\/\/www.gsbet888.com\/reactions\/2020\/07\/heck-matsuda%e5%8f%8d%e5%ba%94%ef%bc%88%e4%b8%89%ef%bc%89.html","title":{"rendered":"Heck-Matsuda\u53cd\u5e94\uff08\u4e09\uff09"},"content":{"rendered":"

\u672c\u671f\u5c0f\u7f16\u4e3a\u5404\u4f4d\u540c\u884c\u4ecb\u7ecd\u5bf9\u6620\u9009\u62e9\u6027Heck-Matsuda\u53cd\u5e94\u3002<\/p>\n

\u6982\u8981<\/strong><\/h4>\n
2011\u5e74\uff0cB. Schmidt\u901a\u8fc7\u915a\u7f9f\u57fa\u53d6\u4ee3\u82b3\u9999\u91cd\u6c2e\u76d0\u53c2\u4e0e\u7684\u4e0d\u5bf9\u79f0Heck-Matsuda\u53cd\u5e94\uff0c\u9996\u6b21\u5b8c\u6210(3S,7R)- 5,6-dehydro-de-O-methyl centrolobine\u7684\u5408\u6210^{[1]<\/sup>\u3002<\/p>\n}
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2012\u5e74\uff0cM. S. Sigman\u91c7\u7528\u624b\u6027PyrOx\u914d\u4f53 (\u53c8\u79f0\u4e3aPyOx, pyridine oxazoline), \u5bf9\u82b3\u9999\u91cd\u6c2e\u76d0\u4e0e(Z)-\u70ef\u4e19\u9187\u3001(E)-\u70ef\u4e19\u9187\u53ca\u9ad8\u70ef\u4e19\u9187\u4e4b\u95f4\u7684\u5bf9\u6620\u9009\u62e9\u6027Heck-Matsuda\u5076\u8054\u8fc7\u7a0b\u8fdb\u884c\u4e86\u7cfb\u7edf\u7814\u7a76\uff0c\u5e76\u987a\u5229\u5b9e\u73b0\u624b\u6027\u03b2-\u82b3\u7fb0\u57fa\u5316\u5408\u7269\u3001\u624b\u6027\u03b3-\u82b3\u7fb0\u57fa\u5316\u5408\u7269\u4e0e\u624b\u6027\u03b4-\u82b3\u7fb0\u57fa\u5316\u5408\u7269\u7684\u4e0d\u5bf9\u79f0\u5408\u6210^{[2]<\/sup>\u3002<\/p>\n}
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2014\u5e74\uff0cC. R. D. Correia\u5c06\u8be5\u914d\u4f53\u5e94\u7528\u4e8e3-\u73af\u620a\u70ef\u9187\u7684\u5bf9\u6620\u9009\u62e9\u6027\u53bb\u5bf9\u79f0\u5316^{[3]<\/sup>\u3002<\/p>\n}
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2015\u5e74\uff0cC. R. D. Correia\u901a\u8fc7\u624b\u6027QuinOx (quinoline oxazoline)\u914d\u4f53\uff0c\u8fdb\u4e00\u6b65\u5b9e\u73b0\u5185\u6d88\u65cbcis-4-\u73af\u620a\u70ef-1,3-\u4e8c\u9187\u7684\u5bf9\u6620\u9009\u62e9\u6027\u53bb\u5bf9\u79f0\u5316^{[4]<\/sup>\u3002<\/p>\n}
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2012\u5e74\u5f00\u59cb\uff0cC. R. D. Correia\u901a\u8fc7\u624b\u6027BOX\u914d\u4f53 (bisoxazoline)\uff0c\u8bbe\u8ba1\u51fa\u9996\u4f8b\u82b3\u9999\u91cd\u6c2e\u76d0\u4e0e\u73af\u70ef\u57fa\u5316\u5408\u7269\u4e4b\u95f4\u7684\u5bf9\u6620\u9009\u62e9\u6027Heck-Matsuda\u4ea4\u53c9\u5076\u8054\u53cd\u5e94^{[5]<\/sup>\u3002<\/p>\n}
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2013\u5e74, C. R. D. Correia\u7ee7\u7eed\u5c06\u8be5\u914d\u4f53\u5e94\u7528\u4e8e\u82b3\u9999\u91cd\u6c2e\u76d0\u4e0e\u975e\u73af\u70ef\u5316\u5408\u7269\u4e4b\u95f4\u5bf9\u6620\u9009\u62e9\u6027Heck-Matsuda\u4ea4\u53c9\u5076\u8054\u53cd\u5e94\u7684\u8bbe\u8ba1\u3002\u540c\u65f6\uff0cC. R. D. Correia\u53d1\u73b0\uff0c\u901a\u8fc7\u8fdb\u4e00\u6b65\u53cd\u5e94\uff0c\u80fd\u591f\u987a\u5229\u5b8c\u6210\u624b\u6027\u03b2-\u82b3\u57fa-\u03b3-\u5185\u916f\u4e0e\u624b\u6027\u03b2-\u82b3\u57fa\u919b\u7684\u6784\u5efa^{[6]<\/sup>\u3002<\/p>\n}
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2016\u5e74\uff0cC. R. D. Correia\u901a\u8fc7\u65b0\u53d1\u5c55\u7684\u975e\u5171\u4ef7\u7f9f\u57fa\u5bfc\u5411\u7684\u73af\u620a\u70ef\u9187\u5bf9\u6620\u9009\u62e9\u6027\u53bb\u5bf9\u79f0\u5316\u65b9\u6cd5\u5b66\uff0c\u6210\u529f\u5b8c\u6210\u9ad8\u5ea6\u5b98\u80fd\u56e2\u5316\u7684\u624b\u6027cis-4-\u82b3\u57fa\u73af\u620a\u70ef\u9187\u9aa8\u67b6\u7684\u6784\u7b51^{[7]<\/sup>\u3002<\/p>\n}
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\u540c\u65f6\uff0cC. R. D. Correia\u901a\u8fc7\u65b0\u53d1\u5c55\u7684\u624b\u6027PyraBOX (N,N-ligand pyrazinebisoxazoline)\u914d\u4f53\uff0c\u5c06Heck-Matsuda\u5076\u8054\u65b9\u6cd5\u5b66\u5e94\u7528\u4e8e\u5177\u6709S-\u4e0eP-\u7acb\u4f53\u751f\u6210\u4e2d\u5fc3\u7684\u624b\u6027\u6742\u73af\u5206\u5b50\u7684\u6784\u7b51^{[8]<\/sup>\u3002<\/p>\n}
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2017\u5e74\uff0cC. R. D. Correia\u91c7\u7528\u975e\u5171\u4ef7\u7fb0\u57fa\u5bfc\u5411\u7684\u5bf9\u6620\u9009\u62e9\u6027\u53bb\u5bf9\u79f0\u5316\u7b56\u7565\uff0c\u8fdb\u4e00\u6b65\u5c06Heck-Matsuda\u5076\u8054\u65b9\u6cd5\u5b66\u5e94\u7528\u4e8e\u5b63\u78b3\u87ba\u624b\u6027\u4e2d\u5fc3\u7684\u6784\u5efa^{[9]<\/sup>\u3002<\/p>\n}
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\u540c\u65f6\uff0cR. B. Sunoj\u4e0eF. D. Toste\u901a\u8fc7CAPT (chiral anion phase transfer)\u7b56\u7565\uff0c\u5373\u91c7\u7528BINOL\u884d\u751f\u7684\u624b\u6027\u78f7\u9178 (BINOL-derived phosphoric acid)\u6216BINAM (chiral 2,2′-binaphthyl diamine)\u884d\u751f\u7684\u624b\u6027\u78f7\u9178 (BINAM-derived phosphoric acid, BDPA)\u4f5c\u4e3a\u53cd\u8377\u79bb\u5b50\u7684\u82b3\u9999\u91cd\u6c2e\u76d0\u53c2\u4e0eHeck-Matsuda\u5076\u8054\u8fc7\u7a0b\u3002\u7814\u7a76\u8868\u660e\uff0c\u901a\u8fc7\u8be5\u7b56\u7565\uff0c\u80fd\u591f\u6781\u5927\u51cf\u5c11\u526f\u53cd\u5e94\u7684\u53d1\u751f\u3002\u540c\u65f6\u63d0\u9ad8\u4e86\u5076\u8054\u4ea7\u7269\u7684\u6536\u7387\u4e0e\u53cd\u5e94\u7684\u5bf9\u6620\u9009\u62e9\u6027^{[10]<\/sup>\u3002<\/p>\n}
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2018\u5e74\uff0cC. R. D. Correia\u901a\u8fc7\u624b\u6027BOX\u914d\u4f53\uff0c\u5b8c\u6210\u9996\u4f8b\u82b3\u9999\u91cd\u6c2e\u76d0\u53c2\u4e0e\u7684\u5bf9\u6620\u9009\u62e9\u6027\u5206\u5b50\u5185\u73af\u5916\u7fb0\u57fa\u5316\u5076\u8054 (exocarbonylative coupling)\u53cd\u5e94^{[11]<\/sup>\u3002<\/p>\n}
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\u4e4b\u540e\uff0c\u8be5\u5c0f\u7ec4\u901a\u8fc7\u975e\u5171\u4ef7\u5e95\u7269\u5bfc\u5411 (non-covalent substrate directable)\u7b56\u7565\uff0c\u987a\u5229\u5b9e\u73b0\u975e\u6d3b\u5316\u7684\u4e94\u5143\u73af\u70ef\u57fa\u5316\u5408\u7269\u7684\u5bf9\u6620\u9009\u62e9\u6027Heck-Matsuda\u82b3\u57fa\u5316\uff0c\u5b8c\u6210\u624b\u6027cis-\u4e8c\u53d6\u4ee3\u82b3\u57fa\u73af\u620a\u70ef\u7684\u5408\u6210^{[12]<\/sup>\u3002\u540c\u65f6\uff0c\u901a\u8fc7DFT\u8ba1\u7b97\u8868\u660e\uff0c\u901a\u8fc7\u4f9b\u4f53\u5b98\u80fd\u56e2\u4e0e\u94af\u9633\u79bb\u5b50\u50ac\u5316\u5242\u4e4b\u95f4\u7684\u5185\u90e8\u7a33\u5b9a\u5316\u7684\u914d\u4f4d\u5c42\u5916\u79bb\u5b50-\u5076\u6781\u76f8\u4e92\u4f5c\u7528 (internal stabilizing out-of-coordination-sphere ion-dipole interaction)\u4ea7\u751f\u7684\u975e\u5171\u4ef7\u5bfc\u5411\u6548\u5e94 (non-covalent directing effect)\u63a7\u5236\u53cd\u5e94\u8fc7\u7a0b\u7684\u5bf9\u6620\u9009\u62e9\u6027^{[12]<\/sup>\u3002<\/p>\n}}
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2019\u5e74\uff0cX. Hou\u8fdb\u4e00\u6b65\u5c06\u624b\u6027BOX\u914d\u4f53\u5e94\u7528\u4e8e1,4-\u4e8c\u6c22\u55b9\u5549\u4e0e\u82b3\u9999\u91cd\u6c2e\u76d0\u7684\u4e0d\u5bf9\u79f0Heck-Matsuda\u4ea4\u53c9\u5076\u8054^{[13]<\/sup>\u3002<\/p>\n}
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\u540c\u65f6\uff0c B. Schmidt\u8fdb\u4e00\u6b65\u5c06Heck-Matsuda\u5076\u8054\u7b56\u7565\u5e94\u7528\u4e8e\u5404\u7c7b\u70ef\u7cd6 (glycal)\u7684\u82b3\u57fa\u5316\u3002\u4ece\u800c\u6784\u5efa\u8d77\u4e00\u7cfb\u5217\u82b3\u57faC-\u7cd6\u82f7 (Aryl C-Glycosides)\u7c7b\u5316\u5408\u7269^{[14]<\/sup>\u3002<\/p>\n}
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\u57fa\u672c\u6587\u732e<\/strong><\/h4>\n
\n
[1] B. Schmidt, F. H\u00f6lter, A. Kelling, U. Schilde, J. Org. Chem. 2011, 76, 3357. doi:10.1021\/jo2002787<\/a>.<\/li>\n

[2] E. W. Werner, T. Mei, A. J. Burckle, M. S. Sigman, Science 2012, 338, 1455. doi:10.1126\/science.1229208.<\/a><\/li>\n

[3] R.A. Angnes, J. M. Oliveira, C. C. Oliveira, N. C. Martins, C. R. D. Correia, Chem.-Eur. J. 2014, 20, 13117. doi:10.1002\/chem.201404159<\/a>.<\/li>\n

[4] R. C.\u00a0Carmona, C. R. D. Correia, Adv. Synth. Catal. 2015, 357, 2639. doi:10.1002\/adsc.201500281<\/a>.<\/li>\n

[5] C. R. D. Correia, Caio C. Oliveira, A. G. Salles Jr, E. A. F. Santos, Tetrahedron Lett. 2012, 53, 3325. doi:10.1016\/j.tetlet.2012.04.079<\/a>.<\/li>\n

[6] C. C. Oliveira, Angnes, A. Ricardo, C. R. D. Correia, J. Org. Chem. 2013, 78, 4373. doi:10.1021\/jo400378g<\/a>.<\/li>\n

[7] J. de Oliveira Silva, R. A. Angnes, V. H. Menezes da Silva, B. M. Servilha, M. Adeel, A. A. C. Braga, A. Aponick, C. R. D. Correia, J. Org. Chem. 2016, 81, 2010. doi:10.1021\/acs.joc.5b02846.<\/a><\/li>\n

[8] F. de Azambuja, R. C. Carmona, T. H. D. Chorro, G. Heerdt, C. R. D. Correia, Chem.- Eur. J. 2016, 22, 11205. doi:10.1002\/chem.201602572<\/a>.<\/li>\n

[9] S. Kattela, G. Heerdt, C. R. D. Correia, Adv. Synth. Catal. 2017, 359, 260. doi:10.1002\/adsc.201600946<\/a>.<\/li>\n

[10] C. M. Avila, J. S. Patel, Y. Reddi, M. Saito, H. M. Nelson, H. P. Shunatona, M. S. Sigman, R. B. Sunoj, F. D. Toste, Angew. Chem. Int. Ed. 2017, 56, 5806. doi:10.1002\/anie.201702107<\/a>.<\/li>\n

[11] C. R. D. Correia, R. C. Carmona, O. D. K\u00f6ster, Angew. Chem. Int. Ed. 2018, 57, 12067. doi:10.1002\/anie.201805831<\/a>.<\/li>\n

[12] C. R. D. Correia, J. Oliveira, R. A. Angnes, I. U. Khan, E. C. Polo, G. Heerdt, B. Servilha, V. Silva, A. Braga, Chem.-Eur. J. 2018, 24, 11738. doi:10.1002\/chem.201801910.<\/a><\/li>\n

[13] Z. Jiang, Y. Jiang, J. Du, D. Chen, C. Ding, B. Xu, X. Hou, Synthesis 2019, 51, 3269. doi:10.1055\/s-0037-1610712.<\/a><\/li>\n

[14] F. Otte, B. Schmidt, J. Org. Chem. 2019, 84, 14816. doi:10.1021\/acs.joc.9b02410<\/a>.<\/li>\n<\/ul>\n
\u53cd\u5e94\u673a\u7406<\/strong><\/h4>\n
\u624b\u6027<\/strong>PyrOx<\/strong>\u914d\u4f53\u53c2\u4e0e\u7684\u4e0d\u5bf9\u79f0<\/strong>Heck-Matsuda<\/strong>\u53cd\u5e94<\/strong>^{[1]-[4]<\/sup><\/p>\n}
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<\/a><\/p>\n
\u624b\u6027<\/strong>QuinOx<\/strong>\u914d\u4f53\u53c2\u4e0e\u7684\u4e0d\u5bf9\u79f0<\/strong>Heck-Matsuda<\/strong>\u53cd\u5e94<\/strong>^{[5]<\/sup><\/p>\n}
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\u624b\u6027<\/strong>BOX<\/strong>\u914d\u4f53\u53c2\u4e0e\u7684\u4e0d\u5bf9\u79f0<\/strong>Heck-Matsuda<\/strong>\u53cd\u5e94<\/strong>^{[6]<\/sup><\/p>\n}
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<\/a><\/p>\n
\u624b\u6027<\/strong>PyraBOX<\/strong>\u914d\u4f53\u53c2\u4e0e\u7684\u4e0d\u5bf9\u79f0<\/strong>Heck-Matsuda<\/strong>\u53cd\u5e94<\/strong>^{[7]-[9]<\/sup><\/p>\n}
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<\/a><\/p>\n
\u901a\u8fc7<\/strong>CAPT<\/strong>\u7b56\u7565\u8fdb\u884c\u7684\u4e0d\u5bf9\u79f0<\/strong>Heck-Matsuda<\/strong>\u53cd\u5e94<\/strong>^{[10]-[14]<\/sup><\/p>\n}
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\u53c2\u8003\u6587\u732e<\/strong><\/h4>\n
\n
[1] B. Schmidt, F. Wolf, H. Brunner, Eur. J. Org. Chem. 2016, 2972. doi:10.1002\/ejoc.201600469<\/a>.<\/li>\n

[2] M. Oestreich, Angew. Chem. Int. Ed. 2014, 53, 2282. doi:10.1002\/anie.201310585<\/a>.<\/li>\n

[3] R.A. Angnes, J. M. Oliveira, C. C. Oliveira, N. C. Martins, C. R. D. Correia, Chem.-Eur. J. 2014, 20, 13117. doi:10.1002\/chem.201404159<\/a>.<\/li>\n

[4] C. C. Oliveira, E. A. F. dos Santos, J. H. B. Nunes, C. R. D. Correia, J. Org. Chem. 2012, 77, 8182. doi:10.1021\/jo3015209<\/a>.<\/li>\n

[5] M. S. Sigman, Erik W.Werner, Acc. Chem. Res.\u00a02012, 45, 6, 874. doi:10.1021\/ar200236v<\/a>.<\/li>\n

[6] C. C. Oliveira, Angnes, A. Ricardo, C. R. D. Correia, J. Org. Chem. 2013, 78, 4373. doi:10.1021\/jo400378g<\/a>.<\/li>\n

[7] F. de Azambuja, R. C. Carmona, T. H. D. Chorro, G. Heerdt, C. R. D. Correia, Chem.- Eur. J. 2016, 22, 11205. doi:10.1002\/chem.201602572<\/a>.<\/li>\n

[8] S. Kattela, G. Heerdt, C. R. D. Correia, Adv. Synth. Catal. 2017, 359, 260. doi:10.1002\/adsc.201600946<\/a>.<\/li>\n

[9] V. H. M. da Silva, C. C. Oliveira, C. R. D. Correia, A. A. C. Braga, Theor. Chem. Acc.\u00a02020, 139,\u00a077. doi:10.1007\/s00214-020-02588-x<\/a>.<\/li>\n

[10] G. Jindal, R. B. Sunoj, J. Org. Chem. 2014, 79, 7600. doi:10.1021\/jo501322v<\/a>.<\/li>\n

[11] Y. Reddi, C. Tsai, C. M. Avila, F. D. Toste, R. B. Sunoj, J. Am. Chem. Soc. 2019, 141, 998. doi:10.1021\/jacs.8b11062<\/a>.<\/li>\n

[12] A. R. Kapdi, A. C. Whitwood, D. C. Williamson, J. M. Lynam, M. J. Burns, T. J. Williams, A. J. Reay, J. Holmes, I. J. S. Fairlamb, J. Am. Chem. Soc. 2013, 135, 8388. doi:10.1021\/ja403259c.<\/a><\/li>\n

[13] L. B. Belykh, N. I. Skripov, L. N. Belonogova, V. A. Umanets, T. P. Stepanova, F. K. Schmidt, Kinetics and Catalysis, 2011, 52, 702. doi:10.1134\/S002315841105003X<\/a>.<\/li>\n

[14] T. Ukai, H. Kawazura, Y. Ishii, J.J. Bonnet, J. A. Ibers, J. Organomet. Chem. 1974, 65, 253. doi:10.1016\/S0022-328X(00)91277-4<\/a>.<\/li>\n<\/ul>\n
\u53cd\u5e94\u5b9e\u4f8b<\/strong><\/h4>\n
\u5bf9\u6620\u9009\u62e9\u6027Oxy-Heck-Matsuda\u82b3\u57fa\u5316^{[6]<\/sup><\/p>\n}
<\/a><\/p>\n
(-)-Codonopsinine\u7684\u5bf9\u6620\u9009\u62e9\u6027\u5168\u5408\u6210^{[2]<\/sup><\/p>\n}
<\/a><\/p>\n
(-)-isoaltholactone\u7684\u5408\u6210^{[3]<\/sup><\/p>\n}
<\/a><\/p>\n
\u73af\u620a\u70ef\u4e0e\u73af\u5df1\u70ef\u884d\u751f\u7269\u7684\u5bf9\u6620\u9009\u62e9\u6027\u82b3\u57fa\u5316^{[4]<\/sup><\/p>\n}
<\/a><\/p>\n
\u5b9e\u9a8c\u6b65\u9aa4<\/strong><\/h4>\n
\u624b\u6027<\/strong>PyrOx<\/strong>\u914d\u4f53\u53c2\u4e0e\u7684\u4e0d\u5bf9\u79f0<\/strong>Heck-Matsuda<\/strong>\u53cd\u5e94<\/strong><\/span><\/p>\n
\u5411\u653e\u6709\u78c1\u529b\u6405\u62cc\u5b50\u7684\u53cd\u5e94\u7ba1\u4e2d\u52a0\u5165\u4e09\u6c1f\u4e59\u9178\u94af(0.025 eq.)\u3001\u624b\u6027PyrOx\u914d\u4f53 (0.05 eq.)\u4e0e\u7532\u9187 (\u7ef4\u6301\u5e95\u7269\u6d53\u5ea6\u4e3a0.075 M)\u3002\u5c06\u4e0a\u8ff0\u5747\u76f8\u6df7\u5408\u7269\u572840^{o<\/sup>C\u4e0b\u6405\u62cc10 min\u300210 min\u540e\uff0c\u518d\u52a0\u4ebaDTBMP (1 eq.)\u4e0e\u70ef\u57fa\u5316\u5408\u7269 (2 eq.)\u3002\u968f\u540e\uff0c\u52a0\u5165\u56db\u6c1f\u787c\u9178\u82b3\u9999\u91cd\u6c2e\u76d0 (1 eq.)\u3002\u5c06\u4e0a\u8ff0\u53cd\u5e94\u6df7\u5408\u7269\u7ee7\u7eed\u6405\u62cc\uff0c\u5e76\u901a\u8fc7TLC\u76d1\u63a7\u76f4\u81f3\u53cd\u5e94\u7ed3\u675f\u3002\u53cd\u5e94\u7ed3\u675f\u540e\uff0c\u5c06\u4e0a\u8ff0\u6df7\u5408\u7269\u8fdb\u884c\u51cf\u538b\u6d53\u7f29\u3002\u518d\u52a0\u5165\u4e59\u9178\u4e59\u916f\/\u6b63\u5df1\u70f7 (1:1 v\/v) \u8fdb\u884c\u6eb6\u89e3\uff0c\u5e76\u901a\u8fc7\u77ed\u7845\u80f6\u67f1\u8fc7\u6ee4\uff0c\u9664\u53bb\u6781\u6027\u7ec4\u5206\u3002\u6ee4\u6db2\u901a\u8fc7\u51cf\u538b\u9664\u53bb\u6eb6\u5242\u540e\uff0c\u83b7\u5f97\u7c97\u4ea7\u7269\u3002\u5c06\u7c97\u4ea7\u7269\u901a\u8fc7\u5feb\u901f\u67f1\u8272\u8c31 (\u4e59\u9178\u4e59\u916f\/\u6b63\u5df1\u70f77:3 v\/v \u4f5c\u4e3a\u6d17\u8131\u5242)\u5206\u79bb\u7eaf\u5316\uff0c\u83b7\u5f97\u76f8\u5e94\u76ee\u6807\u4ea7\u7269\u3002<\/p>\n}
\u624b\u6027<\/strong>QuinOx<\/strong>\u914d\u4f53\u53c2\u4e0e\u7684\u4e0d\u5bf9\u79f0<\/strong>Heck-Matsuda<\/strong>\u53cd\u5e94<\/strong><\/span><\/p>\n
\u5411\u653e\u6709\u78c1\u529b\u6405\u62cc\u5b50\u7684\u5bc6\u5c01\u53cd\u5e94\u74f6\u4e2d\u52a0\u5165\u4e09\u6c1f\u4e59\u9178\u94af (0.01-0.1 eq.)\u3001\u624b\u6027QuinOx\u914d\u4f53 (0.02-0.2 eq.)\u4e0e\u7532\u9187 (\u7ef4\u6301\u5e95\u7269\u6d53\u5ea6\u4e3a0.1 M)\u3002\u5c06\u4e0a\u8ff0\u5747\u76f8\u6df7\u5408\u7269\u572840^{o<\/sup>C\u4e0b\u6405\u62cc5 min\u30025 min\u540e\uff0c\u5c06\u53cd\u5e94\u74f6\u51b7\u5374\u81f3\u5ba4\u6e29\uff0c\u518d\u52a0\u4eba\u78b3\u9178\u950c (0.5 eq.)\u3001\u70ef\u57fa\u5316\u5408\u7269 (2 eq.)\u53ca\u56db\u6c1f\u787c\u9178\u82b3\u9999\u91cd\u6c2e\u76d0 (1 eq.)\u3002\u5c06\u4e0a\u8ff0\u53cd\u5e94\u6df7\u5408\u7269\u5347\u6e29\u81f340^{o<\/sup>C\uff0c\u7ee7\u7eed\u6405\u62cc\uff0c\u5e76\u901a\u8fc7TLC\u76d1\u63a7\u76f4\u81f3\u53cd\u5e94\u7ed3\u675f\u3002\u53cd\u5e94\u7ed3\u675f\u540e\uff0c\u5c06\u4e0a\u8ff0\u6df7\u5408\u7269\u8fdb\u884c\u51cf\u538b\u6d53\u7f29\u3002\u518d\u52a0\u5165\u4e59\u9178\u4e59\u916f\u6eb6\u89e3\uff0c\u5e76\u901a\u8fc7\u77ed\u7845\u80f6\u67f1\u8fc7\u6ee4\u3002\u6ee4\u6db2\u901a\u8fc7\u51cf\u538b\u9664\u53bb\u6eb6\u5242\u540e\uff0c\u83b7\u5f97\u7c97\u4ea7\u7269\u3002\u5c06\u7c97\u4ea7\u7269\u901a\u8fc7\u5feb\u901f\u67f1\u8272\u8c31\u5206\u79bb\u7eaf\u5316\uff0c\u83b7\u5f97\u76f8\u5e94\u76ee\u6807\u4ea7\u7269\u3002<\/p>\n}}
\u624b\u6027<\/strong>BOX<\/strong>\u914d\u4f53\u53c2\u4e0e\u7684\u4e0d\u5bf9\u79f0<\/strong>Heck-Matsuda<\/strong>\u53cd\u5e94<\/strong><\/span><\/p>\n
\u5411\u653e\u6709\u78c1\u529b\u6405\u62cc\u5b50\u7684\u53cd\u5e94\u7ba1\u4e2d\u52a0\u5165\u4e09\u6c1f\u4e59\u9178\u94af (0.025 eq.)\u3001\u624b\u6027BOX\u914d\u4f53 (0.05 eq.)\u4e0e\u7532\u9187 (\u7ef4\u6301\u5e95\u7269\u6d53\u5ea6\u4e3a0.075 M)\u3002\u5c06\u4e0a\u8ff0\u5747\u76f8\u6df7\u5408\u7269\u572840^{o<\/sup>C\u4e0b\u6405\u62cc10 min\u300210 min\u540e\uff0c\u518d\u52a0\u4ebaDTBMP (1 eq.)\u4e0e\u70ef\u57fa\u5316\u5408\u7269 (2 eq.)\uff0c\u968f\u540e\uff0c\u52a0\u5165\u56db\u6c1f\u787c\u9178\u82b3\u9999\u91cd\u6c2e\u76d0 (1 eq.)\u3002\u5c06\u4e0a\u8ff0\u53cd\u5e94\u6df7\u5408\u7269\u7ee7\u7eed\u6405\u62cc\uff0c\u5e76\u901a\u8fc7TLC\u76d1\u63a7\u76f4\u81f3\u53cd\u5e94\u7ed3\u675f\u3002\u53cd\u5e94\u7ed3\u675f\u540e\uff0c\u5c06\u4e0a\u8ff0\u6df7\u5408\u7269\u8fdb\u884c\u51cf\u538b\u6d53\u7f29\u3002\u518d\u52a0\u5165\u4e59\u9178\u4e59\u916f\/\u6b63\u5df1\u70f7 (1:1 v\/v) \u6eb6\u89e3\uff0c\u5e76\u901a\u8fc7\u77ed\u7845\u80f6\u67f1\u8fc7\u6ee4\uff0c\u9664\u53bb\u6781\u6027\u7ec4\u5206\u3002\u6ee4\u6db2\u901a\u8fc7\u51cf\u538b\u9664\u53bb\u6eb6\u5242\u540e\uff0c\u83b7\u5f97\u7c97\u4ea7\u7269\u3002\u5c06\u7c97\u4ea7\u7269\u901a\u8fc7\u5feb\u901f\u67f1\u8272\u8c31 (\u4e59\u9178\u4e59\u916f\/\u6b63\u5df1\u70f77:3 v\/v \u4f5c\u4e3a\u6d17\u8131\u5242)\u5206\u79bb\u7eaf\u5316\uff0c\u83b7\u5f97\u76f8\u5e94\u76ee\u6807\u4ea7\u7269\u3002<\/p>\n}
\u624b\u6027<\/strong>PyraBOX<\/strong>\u914d\u4f53\u53c2\u4e0e\u7684\u4e0d\u5bf9\u79f0<\/strong>Heck-Matsuda<\/strong>\u53cd\u5e94<\/strong><\/span><\/p>\n
\u5411\u653e\u6709\u78c1\u529b\u6405\u62cc\u5b50\u7684\u5bc6\u5c01\u53cd\u5e94\u74f6\u4e2d\u52a0\u5165\u4e09\u6c1f\u4e59\u9178\u94af (0.025 eq.)\u3001\u624b\u6027PyraBOX\u914d\u4f53 (0.03 eq.)\u4e0e\u7532\u9187 (\u7ef4\u6301\u5e95\u7269\u6d53\u5ea6\u4e3a0.1 M)\u3002\u5c06\u4e0a\u8ff0\u5747\u76f8\u6df7\u5408\u7269\u572860^{o<\/sup>C\u4e0b\u6405\u62cc7-8 min\u30027-8 min\u540e\uff0c\u5c06\u53cd\u5e94\u74f6\u51b7\u5374\u81f3\u5ba4\u6e29\uff0c\u518d\u52a0\u4eba\u70ef\u57fa\u5316\u5408\u7269 (1 eq.)\u3002\u968f\u540e\uff0c\u52a0\u5165\u78b1 (1 eq.)\u53ca\u56db\u6c1f\u787c\u9178\u82b3\u9999\u91cd\u6c2e\u76d0 (1.2 eq.)\u3002\u5c06\u4e0a\u8ff0\u53cd\u5e94\u6df7\u5408\u7269\u5347\u6e29\u81f340^{o<\/sup>C\uff0c\u7ee7\u7eed\u6405\u62cc\uff0c\u5e76\u901a\u8fc7TLC\u76d1\u63a7\u76f4\u81f3\u53cd\u5e94\u7ed3\u675f\u3002\u53cd\u5e94\u7ed3\u675f\u540e\uff0c\u5c06\u4e0a\u8ff0\u6df7\u5408\u7269\u8fdb\u884c\u51cf\u538b\u6d53\u7f29\u3002\u518d\u52a0\u5165\u4e59\u9178\u4e59\u916f\u6eb6\u89e3\uff0c\u5e76\u901a\u8fc7\u77ed\u7845\u80f6\u67f1\u8fc7\u6ee4\u3002\u6ee4\u6db2\u901a\u8fc7\u51cf\u538b\u9664\u53bb\u6eb6\u5242\u540e\uff0c\u83b7\u5f97\u7c97\u4ea7\u7269\u3002\u5c06\u7c97\u4ea7\u7269\u901a\u8fc7\u5feb\u901f\u67f1\u8272\u8c31\u5206\u79bb\u7eaf\u5316\uff0c\u83b7\u5f97\u76f8\u5e94\u76ee\u6807\u4ea7\u7269\u3002<\/p>\n}}
\u901a\u8fc7<\/strong>CAPT<\/strong>\u7b56\u7565\u8fdb\u884c\u7684\u4e0d\u5bf9\u79f0<\/strong>Heck-Matsuda<\/strong>\u53cd\u5e94<\/strong><\/span><\/p>\n
\u5411\u5bc6\u5c01\u53cd\u5e94\u74f6\u4e2d\u52a0\u5165\u70ef\u57fa\u5316\u5408\u7269 (1 eq.)\u3001\u624b\u6027\u78f7\u9178 (0.03 eq.)\u4e0e\u78b1 (2 eq.)\u3002\u518d\u52a0\u5165\u7532\u82ef (\u7ef4\u6301\u5e95\u7269\u6d53\u5ea6\u4e3a0.04 M)\uff0c\u5c06\u4e0a\u8ff0\u53cd\u5e94\u6df7\u5408\u7269\u6405\u62cc10 min\u300210 min\u540e\uff0c\u52a0\u5165\u4e09\u6c1f\u4e59\u9178\u94af (0.0005 eq.)\u53ca\u56db\u6c1f\u787c\u9178\u82b3\u9999\u91cd\u6c2e\u76d0 (1.36 eq.)\u3002\u5c06\u4e0a\u8ff0\u53cd\u5e94\u6df7\u5408\u7269\u7ee7\u7eed\u6405\u62cc\uff0c\u5e76\u901a\u8fc7TLC\u76d1\u63a7\u76f4\u81f3\u53cd\u5e94\u7ed3\u675f\u3002\u53cd\u5e94\u7ed3\u675f\u540e\uff0c\u5c06\u4e0a\u8ff0\u6df7\u5408\u7269\u901a\u8fc7\u77ed\u7845\u80f6\u67f1\u8fc7\u6ee4\u3002\u6ee4\u6db2\u901a\u8fc7\u51cf\u538b\u9664\u53bb\u6eb6\u5242\u540e\uff0c\u83b7\u5f97\u7c97\u4ea7\u7269\u3002\u5c06\u7c97\u4ea7\u7269\u901a\u8fc7\u5feb\u901f\u67f1\u8272\u8c31 (\u6b63\u620a\u70f7\/\u4e59\u9178\u4e59\u916f19:5 v\/v\u53ca 9:1 v\/v\u8fdb\u884c\u68af\u5ea6\u6d17\u8131)\u5206\u79bb\u7eaf\u5316\uff0c\u83b7\u5f97\u76f8\u5e94\u76ee\u6807\u4ea7\u7269\u3002<\/p>\n
\u53c2\u8003\u6587\u732e<\/strong><\/h4>\n \n
[1] C. R. D. Correia, A. Ribeiro, E. Polo, N. Martins, Adv. Synth. Catal. 2018, 360, 346. doi:10.1002\/adsc.201701278<\/a>.<\/li>\n

[2] E. A. Severino, C.R.D. Correia, Org. Lett. 2000, 2, 3039. doi:10.1021\/ol005762d<\/a>.<\/li>\n

[3] P. R. R. Meira, A. V. Moro, C. R. D. Correia, Synthesis 2007, 2279. doi:10.1055\/s-2007-983781.<\/a><\/li>\n

[4] C. M. Avila, J. S. Patel, Y. Reddi, M. Saito, H. M. Nelson, H. P. Shunatona, M. S. Sigman, R. B. Sunoj, F. D. Toste, Angew. Chem. Int. Ed. 2017, 56, 5806. doi:10.1002\/anie.201702107<\/a>.<\/li>\n<\/ul>\n
\u672c\u6587\u7248\u6743\u5c5e\u4e8e\u00a0Chem-Station\u5316\u5b66\u7a7a\u95f4<\/a>\uff0c<\/strong>\u00a0\u6b22\u8fce\u70b9\u51fb\u6309\u94ae\u5206\u4eab\uff0c\u672a\u7ecf\u8bb8\u53ef\uff0c\u8c22\u7edd\u8f6c\u8f7d\uff01<\/p>\n","protected":false},"excerpt":{"rendered":"\u672c\u671f\u5c0f\u7f16\u4e3a\u5404\u4f4d\u540c\u884c\u4ecb\u7ecd\u5bf9\u6620\u9009\u62e9\u6027Heck-Matsuda\u53cd\u5e94\u3002 \u6982\u8981 2011\u5e74\uff0cB. Schmidt\u901a\u8fc7\u915a\u7f9f\u57fa\u53d6\u4ee3\u82b3\u9999\u91cd\u6c2e\u76d0\u53c2\u4e0e\u7684\u4e0d\u5bf9\u79f0Heck-Matsuda\u53cd\u5e94\uff0c\u9996\u6b21\u5b8c\u6210(3S,7R)- 5,6-dehydro-de-O-methyl centrolobine\u7684\u5408\u6210[1]\u3002 2012\u5e74\uff0cM. S. Sigman\u91c7\u7528\u624b\u6027PyrOx\u914d\u4f53 (\u53c8\u79f0\u4e3aPyOx, pyridine oxazoline), \u5bf9\u82b3\u9999\u91cd\u6c2e\u76d0\u4e0e(Z)-\u70ef\u4e19\u9187\u3001(E)-\u70ef\u4e19\u9187\u53ca\u9ad8\u70ef\u4e19\u9187\u4e4b\u95f4\u7684\u5bf9\u6620\u9009\u62e9\u6027Heck-Matsuda\u5076\u8054\u8fc7\u7a0b\u8fdb\u884c\u4e86\u7cfb\u7edf\u7814\u7a76\uff0c\u5e76\u987a\u5229\u5b9e\u73b0\u624b\u6027\u03b2-\u82b3\u7fb0\u57fa\u5316\u5408\u7269\u3001\u624b\u6027\u03b3-\u82b3\u7fb0\u57fa\u5316\u5408\u7269\u4e0e\u624b\u6027\u03b4-\u82b3\u7fb0\u57fa\u5316\u5408\u7269\u7684\u4e0d\u5bf9\u79f0\u5408\u6210[2]\u3002 2014\u5e74\uff0cC. R. D. Correia\u5c06\u8be5\u914d\u4f53\u5e94\u7528\u4e8e3-\u73af\u620a\u70ef\u9187\u7684\u5bf9\u6620\u9009\u62e9\u6027\u53bb\u5bf9\u79f0\u5316[3]\u3002 2015\u5e74\uff0cC. R. D. Correia\u901a\u8fc7\u624b\u6027QuinOx (quinoline oxazoline)\u914d\u4f53\uff0c\u8fdb\u4e00\u6b65\u5b9e\u73b0\u5185\u6d88\u65cbcis-4-\u73af\u620a\u70ef-1,3-\u4e8c\u9187\u7684\u5bf9\u6620\u9009\u62e9\u6027\u53bb\u5bf9\u79f0\u5316[4]\u3002 2012\u5e74\u5f00\u59cb\uff0cC. R. D. Correia\u901a\u8fc7\u624b\u6027BOX\u914d\u4f53 (bisoxazoline)\uff0c\u8bbe\u8ba1\u51fa\u9996\u4f8b\u82b3\u9999\u91cd\u6c2e\u76d0\u4e0e\u73af\u70ef\u57fa\u5316\u5408\u7269\u4e4b\u95f4\u7684\u5bf9\u6620\u9009\u62e9\u6027Heck-Matsuda\u4ea4\u53c9\u5076\u8054\u53cd\u5e94[5]\u3002 2013\u5e74, C. R. D. Correia\u7ee7\u7eed\u5c06\u8be5\u914d\u4f53\u5e94\u7528\u4e8e\u82b3\u9999\u91cd\u6c2e\u76d0\u4e0e\u975e\u73af\u70ef\u5316\u5408\u7269\u4e4b\u95f4\u5bf9\u6620\u9009\u62e9\u6027Heck-Matsuda\u4ea4\u53c9\u5076\u8054\u53cd\u5e94\u7684\u8bbe\u8ba1\u3002\u540c\u65f6\uff0cC. R. D. Correia\u53d1\u73b0\uff0c\u901a\u8fc7\u8fdb\u4e00\u6b65\u53cd\u5e94\uff0c\u80fd\u591f\u987a\u5229\u5b8c\u6210\u624b\u6027\u03b2-\u82b3\u57fa-\u03b3-\u5185\u916f\u4e0e\u624b\u6027\u03b2-\u82b3\u57fa\u919b\u7684\u6784\u5efa[6]\u3002 2016\u5e74\uff0cC. R. D. Correia\u901a\u8fc7\u65b0\u53d1\u5c55\u7684\u975e\u5171\u4ef7\u7f9f\u57fa\u5bfc\u5411\u7684\u73af\u620a\u70ef\u9187\u5bf9\u6620\u9009\u62e9\u6027\u53bb\u5bf9\u79f0\u5316\u65b9\u6cd5\u5b66\uff0c\u6210\u529f\u5b8c\u6210\u9ad8\u5ea6\u5b98\u80fd\u56e2\u5316\u7684\u624b\u6027cis-4-\u82b3\u57fa\u73af\u620a\u70ef\u9187\u9aa8\u67b6\u7684\u6784\u7b51[7]\u3002 \u540c\u65f6\uff0cC. R. D. Correia\u901a\u8fc7\u65b0\u53d1\u5c55\u7684\u624b\u6027PyraBOX (N,N-ligand pyrazinebisoxazoline)\u914d\u4f53\uff0c\u5c06Heck-Matsuda\u5076\u8054\u65b9\u6cd5\u5b66\u5e94\u7528\u4e8e\u5177\u6709S-\u4e0eP-\u7acb\u4f53\u751f\u6210\u4e2d\u5fc3\u7684\u624b\u6027\u6742\u73af\u5206\u5b50\u7684\u6784\u7b51[8]\u3002 2017\u5e74\uff0cC. R. D. Correia\u91c7\u7528\u975e\u5171\u4ef7\u7fb0\u57fa\u5bfc\u5411\u7684\u5bf9\u6620\u9009\u62e9\u6027\u53bb\u5bf9\u79f0\u5316\u7b56\u7565\uff0c\u8fdb\u4e00\u6b65\u5c06Heck-Matsuda\u5076\u8054\u65b9\u6cd5\u5b66\u5e94\u7528\u4e8e\u5b63\u78b3\u87ba\u624b\u6027\u4e2d\u5fc3\u7684\u6784\u5efa[9]\u3002 \u540c\u65f6\uff0cR. B. Sunoj\u4e0eF. D. Toste\u901a\u8fc7CAPT (chiral anion phase transfer)\u7b56\u7565\uff0c\u5373\u91c7\u7528BINOL\u884d\u751f\u7684\u624b\u6027\u78f7\u9178 (BINOL-derived phosphoric acid)\u6216BINAM (chiral 2,2′-binaphthyl diamine)\u884d\u751f\u7684\u624b\u6027\u78f7\u9178 (BINAM-derived phosphoric acid, BDPA)\u4f5c\u4e3a\u53cd\u8377\u79bb\u5b50\u7684\u82b3\u9999\u91cd\u6c2e\u76d0\u53c2\u4e0eHeck-Matsuda\u5076\u8054\u8fc7\u7a0b\u3002\u7814\u7a76\u8868\u660e\uff0c\u901a\u8fc7\u8be5\u7b56\u7565\uff0c\u80fd\u591f\u6781\u5927\u51cf\u5c11\u526f\u53cd\u5e94\u7684\u53d1\u751f\u3002\u540c\u65f6\u63d0\u9ad8\u4e86\u5076\u8054\u4ea7\u7269\u7684\u6536\u7387\u4e0e\u53cd\u5e94\u7684\u5bf9\u6620\u9009\u62e9\u6027[10]\u3002 2018\u5e74\uff0cC. R. D. Correia\u901a\u8fc7\u624b\u6027BOX\u914d\u4f53\uff0c\u5b8c\u6210\u9996\u4f8b\u82b3\u9999\u91cd\u6c2e\u76d0\u53c2\u4e0e\u7684\u5bf9\u6620\u9009\u62e9\u6027\u5206\u5b50\u5185\u73af\u5916\u7fb0\u57fa\u5316\u5076\u8054 (exocarbonylative coupling)\u53cd\u5e94[11]\u3002 \u4e4b\u540e\uff0c\u8be5\u5c0f\u7ec4\u901a\u8fc7\u975e\u5171\u4ef7\u5e95\u7269\u5bfc\u5411 (non-covalent substrate directable)\u7b56\u7565\uff0c\u987a\u5229\u5b9e\u73b0\u975e\u6d3b\u5316\u7684\u4e94\u5143\u73af\u70ef\u57fa\u5316\u5408\u7269\u7684\u5bf9\u6620\u9009\u62e9\u6027Heck-Matsuda\u82b3\u57fa\u5316\uff0c\u5b8c\u6210\u624b\u6027cis-\u4e8c\u53d6\u4ee3\u82b3\u57fa\u73af\u620a\u70ef\u7684\u5408\u6210[12]\u3002\u540c\u65f6\uff0c\u901a\u8fc7DFT\u8ba1\u7b97\u8868\u660e\uff0c\u901a\u8fc7\u4f9b\u4f53\u5b98\u80fd\u56e2\u4e0e\u94af\u9633\u79bb\u5b50\u50ac\u5316\u5242\u4e4b\u95f4\u7684\u5185\u90e8\u7a33\u5b9a\u5316\u7684\u914d\u4f4d\u5c42\u5916\u79bb\u5b50-\u5076\u6781\u76f8\u4e92\u4f5c\u7528 (internal stabilizing out-of-coordination-sphere ion-dipole interaction)\u4ea7\u751f\u7684\u975e\u5171\u4ef7\u5bfc\u5411\u6548\u5e94 (non-covalent directing effect)\u63a7\u5236\u53cd\u5e94\u8fc7\u7a0b\u7684\u5bf9\u6620\u9009\u62e9\u6027 [12]\u3002 2019\u5e74\uff0cX. Hou\u8fdb\u4e00\u6b65\u5c06\u624b\u6027BOX\u914d\u4f53\u5e94\u7528\u4e8e1,4-\u4e8c\u6c22\u55b9\u5549\u4e0e\u82b3\u9999\u91cd\u6c2e\u76d0\u7684\u4e0d\u5bf9\u79f0Heck-Matsuda\u4ea4\u53c9\u5076\u8054[13]\u3002 \u540c\u65f6\uff0c B. Schmidt\u8fdb\u4e00\u6b65\u5c06Heck-Matsuda\u5076\u8054\u7b56\u7565\u5e94\u7528\u4e8e\u5404\u7c7b\u70ef\u7cd6 (glycal)\u7684\u82b3\u57fa\u5316\u3002\u4ece\u800c\u6784\u5efa\u8d77\u4e00\u7cfb\u5217\u82b3\u57faC-\u7cd6\u82f7 (Aryl C-Glycosides)\u7c7b\u5316\u5408\u7269[14]\u3002 \u57fa\u672c\u6587\u732e [1] B. Schmidt, F. H\u00f6lter, A. Kelling, U. Schilde, J. Org. 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