\u672c\u6587\u4f5c\u8005\uff1a\u6749\u6749<\/p>\n

\u5bfc\u8bfb<\/h4>\n

\u8fd1\u65e5\uff0cWisconsin-Madison\u5927\u5b66\u7684D. J. Weix\u8bfe\u9898\u7ec4\u5728J. Am. Chem. Soc.<\/em>\u4e2d\u53d1\u8868\u8bba\u6587\uff0c\u62a5\u9053\u4e00\u79cd\u5168\u65b0\u7684\u901a\u8fc7Ni\u4e0ePd\u50ac\u5316\u7684\u6742\u82b3\u57fa\u5364\u4e0e\u6742\u82b3\u57fa\u4e09\u6c1f\u7532\u78fa\u9178\u916f\u4e4b\u95f4\u7684\u591a\u91d1\u5c5e\u4ea4\u53c9Ullmann\u5076\u8054\u53cd\u5e94 (multimetallic cross-Ullmann coupling)\u65b9\u6cd5\u5b66\uff0c\u8fdb\u800c\u6210\u529f\u5b8c\u6210\u4e00\u7cfb\u5217\u6742\u73af\u8054\u82b3\u57fa\u5316\u5408\u7269 (biheteroaryl)\u7684\u6784\u5efa\u3002\u8fd9\u4e00\u5168\u65b0\u7684\u4ea4\u53c9\u5076\u8054\u7b56\u7565\u5177\u6709\u53cd\u5e94\u6761\u4ef6\u6e29\u548c\u3001\u5e95\u7269\u8303\u56f4\u5e7f\u6cdb\u4ee5\u53ca\u9ad8\u5ea6\u7684\u5b98\u80fd\u56e2\u517c\u5bb9\u6027\u7b49\u4f18\u52bf\u3002<\/p>\n

A General, Multimetallic Cross-Ullmann Biheteroaryl Synthesis from Heteroaryl Halides and Heteroaryl Triflates<\/p>\n

K. Kang, N. L. Loud, T. A. DiBenedetto, D. J. Weix, J. Am. Chem. Soc.<\/em>\u00a02021<\/strong>, 143, 21484. doi:10.1021\/jacs.1c10907.<\/p><\/blockquote>\n

<\/a><\/p>\n

\u6b63\u6587<\/h4>\n

\u6742\u73af\u8054\u82b3\u57fa\u5316\u5408\u7269\u5e7f\u6cdb\u5b58\u5728\u4e8e\u5404\u7c7b\u836f\u7269\u3001\u7535\u5b50\u6750\u6599\u3001\u914d\u4f53\u4ee5\u53ca\u5929\u7136\u4ea7\u7269\u5206\u5b50\u4e2d\u3002\u7136\u800c\uff0c\u5bf9\u4e8e\u6742\u73af\u8054\u82b3\u57fa\u5316\u5408\u7269\u76f8\u5173\u5408\u6210\u7b56\u7565\u7684\u7814\u7a76\uff0c\u76ee\u524d\u4ecd\u9762\u4e34\u8bf8\u591a\u6311\u6218(Scheme 1)^{[1]-[8]<\/sup>\u3002\u53d7\u5230\u524d\u671f\u5bf9\u4e8e\u4ea4\u53c9Ullmann\u5076\u8054\u53cd\u5e94\u65b9\u6cd5\u5b66[9]<\/sup>\u4ee5\u53ca\u672c\u8bfe\u9898\u7ec4\u5bf9\u4e8e\u591a\u91d1\u5c5e\u50ac\u5316\u7684\u4ea4\u53c9\u5076\u8054\u53cd\u5e94\u65b9\u6cd5\u5b66[10]<\/sup>\u76f8\u5173\u7814\u7a76\u7684\u542f\u53d1\uff0c\u8fd9\u91cc\uff0cD. J. Weix\u8bfe\u9898\u7ec4\u6210\u529f\u8bbe\u8ba1\u51fa\u4e00\u79cd\u5168\u65b0\u7684\u591a\u91d1\u5c5e\u50ac\u5316\u4ea4\u53c9Ullmann\u5076\u8054\u53cd\u5e94\u65b9\u6cd5\u5b66 (Scheme 1)\u3002<\/p>\n}

<\/a><\/p>\n

\u9996\u5148\uff0c\u4f5c\u8005\u91c7\u75281a<\/strong>\u4e0e3-\u6eb4\u5421\u55762a<\/strong>\u4f5c\u4e3a\u6a21\u578b\u5e95\u7269\uff0c\u8fdb\u884c\u76f8\u5173\u5076\u8054\u53cd\u5e94\u6761\u4ef6\u7684\u4f18\u5316\u7b5b\u9009 (Table 1)\u3002\u8fdb\u800c\u786e\u5b9a\u6700\u4f73\u7684\u53cd\u5e94\u6761\u4ef6\u4e3a\uff1a\u91c7\u7528NiBr_{2<\/sub>(dme)\/N1<\/strong>\u4e0ePdCl2<\/sub>\/P1<\/strong>\u4f5c\u4e3a\u50ac\u5316\u5242\uff0cZn\u4f5c\u4e3a\u8fd8\u539f\u5242\uff0c\u65e0\u6c34KBr\u4f5c\u4e3a\u6dfb\u52a0\u5242\uff0cDMF\u4f5c\u4e3a\u53cd\u5e94\u6eb6\u5242\uff0c\u53cd\u5e94\u6e29\u5ea6\u4e3a60^{o<\/sup>C\uff0c\u6700\u7ec8\u83b7\u5f9779%\u6536\u7387\u7684\u5076\u8054\u4ea7\u72693a<\/strong>\u3002<\/p>\n}}

<\/a><\/p>\n

\u5728\u4e0a\u8ff0\u7684\u6700\u4f73\u53cd\u5e94\u6761\u4ef6\u4e0b\uff0c\u4f5c\u8005\u9996\u5148\u5bf9\u5404\u7c7b\u6742\u82b3\u57fa\u6eb4\u4e0e\u6742\u82b3\u57fa\u6c2f\u5e95\u7269\u7684\u5e94\u7528\u8303\u56f4\u8fdb\u884c\u8003\u5bdf (Scheme 2)\u3002\u7814\u7a76\u8868\u660e\uff0c\u4e00\u7cfb\u5217\u516d\u5143\u73af\u3001\u4e94\u5143\u73af\u4e0e\u7a20\u5408\u6742\u73af\u82b3\u57fa\u6eb4\u5e95\u7269\uff0c\u5747\u80fd\u591f\u8f83\u597d\u5730\u4e0e\u4e0a\u8ff0\u7684\u6807\u51c6\u53cd\u5e94\u6761\u4ef6\u517c\u5bb9\uff0c\u5e76\u4ee5\u4e2d\u7b49\u81f3\u4f18\u826f\u7684\u53cd\u5e94\u6536\u7387\uff0c\u83b7\u5f97\u76f8\u5e94\u7684\u4ea4\u53c9\u5076\u8054\u4ea7\u72693a<\/strong>–3z<\/strong>\u4ee5\u53ca3aa-3aj<\/strong>\u3002\u4e4b\u540e\uff0c\u4f5c\u8005\u53d1\u73b0\uff0c\u4e00\u7cfb\u5217\u6742\u82b3\u57fa\u6c2f\u5e95\u7269\uff0c\u540c\u6837\u80fd\u591f\u6709\u6548\u5730\u53c2\u4e0e\u4e0a\u8ff0\u7684\u4ea4\u53c9\u5076\u8054\u8fc7\u7a0b\uff0c\u8fdb\u800c\u4ee5\u4e2d\u7b49\u81f3\u4f18\u826f\u7684\u53cd\u5e94\u6536\u7387\uff0c\u83b7\u5f97\u76f8\u5e94\u7684\u76ee\u6807\u4ea7\u72693ak<\/strong>–3at<\/strong>\u3002\u5e76\u4e14\uff0c\u901a\u8fc7\u6742\u82b3\u57fa\u6c2f\u5e95\u7269\u53c2\u4e0e\u7684\u4ea4\u53c9Ullmann\u5076\u8054\u53cd\u5e94\u65b9\u6cd5\u5b66\u80fd\u591f\u8fdb\u4e00\u6b65\u5e94\u7528\u4e8e\u5404\u7c7b\u836f\u7269\u5206\u5b50 (3as-3at<\/strong>)\u7684\u7ed3\u6784\u4fee\u9970\u3002\u800c\u4e14\uff0c\u4f5c\u8005\u8fdb\u4e00\u6b65\u53d1\u73b0\uff0c\u5c06\u5e95\u72693ao<\/strong>\u7684\u7528\u91cf\u589e\u52a0\u81f35 mmol\u65f6\uff0c\u540c\u6837\u80fd\u591f\u987a\u5229\u5730\u5b8c\u6210\u4e0a\u8ff0\u7684\u4ea4\u53c9\u5076\u8054\u8fc7\u7a0b\u3002\u540c\u65f6\uff0c\u8be5\u5c0f\u7ec4\u89c2\u5bdf\u5230\uff0c\u8fd9\u4e00\u5168\u65b0\u7684\u4ea4\u53c9Ullmann\u5076\u8054\u7b56\u7565\u5bf9\u4e8e\u5404\u7c7b\u4eb2\u7535\u6027\u5b98\u80fd\u56e2 (3g<\/strong>, 3h<\/strong>, 3p<\/strong>, 3q<\/strong>, 3an<\/strong>, 3ao<\/strong>)\u3001\u9178\u654f\u6027\u4fdd\u62a4\u57fa (acid-sensitive protecting groups) (3m, 3s, 3t, 3x, 3ah<\/strong>) \u4e0e\u70ef\u4e19\u57fa (3ag<\/strong>)\u4ee5\u53ca\u5177\u6709\u9ad8\u5ea6\u7acb\u4f53\u4f4d\u963b\u7684\u5404\u7c7b\u57fa\u56e2 (3e<\/strong>, 3o<\/strong>, 3u<\/strong>, 3w<\/strong>,3xaa<\/strong>, 3ac<\/strong>, 3ae<\/strong>)\uff0c\u5747\u8868\u73b0\u51fa\u826f\u597d\u7684\u517c\u5bb9\u6027\u3002\u63a5\u4e0b\u6765\uff0c\u8be5\u5c0f\u7ec4\u7814\u7a76\u53d1\u73b0\uff0c\u91c7\u7528ttbtpy (N3<\/strong>)\u914d\u4f53\u65f6\u00a0 (Conditions B)\uff0c\u80fd\u591f\u6709\u6548\u5730\u6291\u5236\u7f3a\u7535\u5b50\u6742\u82b3\u57fa\u6eb4\u5e95\u7269\u7684\u540c\u5076\u8054\u8fc7\u7a0b\uff0c\u8fdb\u800c\u83b7\u5f97\u76f8\u5e94\u7684\u4ea4\u53c9Ullmann\u5076\u8054\u4ea7\u72693f<\/strong>–3j<\/strong>\u3002<\/p>\n

<\/a><\/p>\n

\u63a5\u4e0b\u6765\uff0c\u4f5c\u8005\u5bf9\u4e00\u7cfb\u5217\u6742\u82b3\u57fa\u4e09\u6c1f\u7532\u78fa\u9178\u916f\u5e95\u7269\u7684\u5e94\u7528\u8303\u56f4\u8fdb\u884c\u6df1\u5165\u7814\u7a76(Scheme 3)\u3002\u8be5\u5c0f\u7ec4\u53d1\u73b0\uff0c\u5404\u7c7b\u5177\u6709\u4e0d\u540c\u7535\u5b50\u6027\u8d28\u7684\u6742\u82b3\u57fa\u4e09\u6c1f\u7532\u78fa\u9178\u916f\u5e95\u7269\uff0c\u5747\u80fd\u591f\u987a\u5229\u5730\u53c2\u4e0e\u4e0a\u8ff0\u7684\u4ea4\u53c9Ullmann\u5076\u8054\u8fc7\u7a0b\uff0c\u5e76\u4ee5\u4e2d\u7b49\u81f3\u4f18\u826f\u7684\u53cd\u5e94\u6536\u7387\uff0c\u83b7\u5f97\u76f8\u5e94\u7684\u4ea7\u72693au<\/strong>–3aai<\/strong>\u3002\u540c\u65f6\uff0c\u7814\u7a76\u8868\u660e\uff0c\u4e0a\u8ff0\u7684\u6807\u51c6\u53cd\u5e94\u4f53\u7cfb\u540c\u6837\u80fd\u591f\u826f\u597d\u5730\u5e94\u7528\u4e8e\u5404\u7c7b\u975e\u82b3\u9999\u70ef\u57fa\u4e09\u6c1f\u7532\u78fa\u9178\u916f (3aaj<\/strong>)\u5e95\u7269\uff0c\u8fdb\u800c\u83b7\u5f97\u826f\u597d\u7684\u53cd\u5e94\u6536\u7387\u3002<\/p>\n

<\/a><\/p>\n

\u63a5\u4e0b\u6765\uff0c\u4f5c\u8005\u901a\u8fc7\u6807\u51c6\u7684\u9ad8\u901a\u91cf\u5b9e\u9a8c (THE, high-throughput experimentation)\u5bf9\u4e0a\u8ff0\u7684\u53cd\u5e94\u6761\u4ef6\u8fdb\u884c\u8fdb\u4e00\u6b65\u4f18\u5316\uff0c\u540c\u65f6\u5bf9\u8fd9\u4e00\u5168\u65b0\u7684\u4ea4\u53c9Ullmann\u5076\u8054\u53cd\u5e94\u7b56\u7565\u5728\u836f\u7269\u5316\u5b66\u4e2d\u7684\u5e94\u7528\u8fdb\u884c\u66f4\u4e3a\u6df1\u5165\u7684\u7814\u7a76 (Figure 1)\u3002<\/p>\n

<\/a><\/p>\n

\u603b\u7ed3<\/strong><\/h4>\n

Wisconsin-Madison\u5927\u5b66\u7684D. J. Weix\u8bfe\u9898\u7ec4\u62a5\u9053\u4e00\u79cd\u5168\u65b0\u7684\u901a\u8fc7Ni\u4e0ePd\u50ac\u5316\u5242\u4fc3\u8fdb\u7684\u6742\u82b3\u57fa\u5364\u4e0e\u6742\u82b3\u57fa\u4e09\u6c1f\u7532\u78fa\u9178\u916f\u4e4b\u95f4\u7684\u591a\u91d1\u5c5e\u4ea4\u53c9Ullmann\u5076\u8054\u53cd\u5e94 (multimetallic cross-Ullmann coupling)\u65b9\u6cd5\u5b66\uff0c\u8fdb\u800c\u987a\u5229\u5b8c\u6210\u4e00\u7cfb\u5217\u6742\u73af\u8054\u82b3\u5206\u5b50\u7684\u6784\u5efa\u3002\u8fd9\u4e00\u5168\u65b0\u7684\u4ea4\u53c9Ullmann\u5076\u8054\u53cd\u5e94\u65b9\u6cd5\u5b66\u5177\u6709\u53cd\u5e94\u6761\u4ef6\u6e29\u548c\u3001\u5e95\u7269\u8303\u56f4\u5e7f\u6cdb\u4ee5\u53ca\u9ad8\u5ea6\u7684\u5b98\u80fd\u56e2\u517c\u5bb9\u6027\u7b49\u4f18\u52bf\u3002\u540c\u65f6\u8be5\u5c0f\u7ec4\u901a\u8fc7\u9ad8\u901a\u91cf\u5b9e\u9a8c\u7684\u8fdb\u4e00\u6b65\u4f18\u5316\uff0c\u8fdb\u4e00\u6b65\u8868\u660e\u8fd9\u4e00\u5168\u65b0\u7684\u4ea4\u53c9Ullmann\u5076\u8054\u5177\u6709\u6f5c\u5728\u7684\u5408\u6210\u5e94\u7528\u4ef7\u503c\u3002<\/p>\n

\u53c2\u8003\u6587\u732e<\/h4>\n[1] (a) V. F. Slagt, A. H. M. de Vries, J. G. de Vries, R. M. Kellogg, Org. Process Res. Dev. <\/em>2010<\/strong>, 14<\/em>, 30. doi: 10.1021\/op900221v<\/a>.<\/p>\n

(b) A. E. Rubtsov, A. V. Malkov, Synthesis<\/em> 2021<\/strong>, 53<\/em>, 2559. doi: 10.1055\/s-0040-1706030.<\/a><\/p>\n[2] C. Cordovilla, C. Bartolome, J. M. Martinez-Ilarduya, P. Espinet, ACS Catal. <\/em>2015<\/strong>, 5<\/em>, 3040. doi: 10.1021\/acscatal.5b00448<\/a>.<\/p>\n[3] V. Snieckus, Chem. Rev. <\/em>1990<\/strong>, 90<\/em>, 879. doi: 10.1021\/cr00104a001<\/a>.<\/p>\n[4] P. A. Cox, M. Reid, A. G. Leach, A. D. Campbell, E.J. King,G. C. Lloyd-Jones, J. Am. Chem. Soc. <\/em>2017<\/strong>, 139<\/em>, 13156. doi: 10.1021\/jacs.7b07444<\/a>.<\/p>\n[5] D. Alberico, M. E. Scott, M. Lautens, Chem.Rev.<\/em>2007<\/strong>, 107<\/em>, 174. doi: 10.1021\/cr0509760<\/a>.<\/p>\n[6] Y. Yang, J. Lan, J. You, Chem. Rev. <\/em>2017<\/strong>, 117<\/em>, 8787. doi: 10.1021\/acs.chemrev.6b00567<\/a>.<\/p>\n[7] T. Markovic, P. R. D. Murray, B. N. Rocke, A. Shavnya, D. C. Blakemore, M. C. Willis, J. Am. Chem. Soc.<\/em>2018<\/strong>, 140<\/em>, 15916. doi: 10.1021\/jacs.8b09595<\/a>.<\/p>\n[8] M. C. Hilton, X. Zhang,B. T. Boyle,J.V. Alegre-Requena,R. S. Paton, A. McNally, Science <\/em>2018<\/strong>, 362<\/em>, 799. doi:\u00a010.1126\/science.aas8961<\/a>.<\/p>\n[9] (a) O. Baudoin, M. Cesario, D. Gu\u00e9nard, F. Gu\u00e9ritte, J. Org. Chem. <\/em>2002<\/strong>, 67<\/em>, 1199. doi: 10.1021\/jo0160726<\/a>.<\/p>\n

(b) C. Gosmini, S. Lasry, J. Y. Nedelec, J. Perichon, Tetrahedron<\/em> 1998<\/strong>, 54<\/em>, 1289. doi: 10.1016\/S0040-4020(97)10225-3<\/a>.<\/p>\n

(c) W. Miao, C. Ni, P. Xiao, R. Jia, W. Zhang, J. Hu, Org. Lett.<\/em> 2021<\/strong>, 23<\/em>, 711. doi: 10.1021\/acs.orglett.0c03939<\/a>.<\/p>\n

(d) S. Sengmany, S. Vasseur, A. Lajnef, E. Le Gall, E. Leonel, Eur. J. Org. Chem. <\/em>2016<\/strong>, 4865. doi: 10.1002\/ejoc.201600790<\/a>.<\/p>\n

(e) A. Dewanji, R. F. B\u00fclow, M. Rueping, Org. Lett.<\/em> 2020<\/strong>, 22<\/em>, 1611. doi: 10.1021\/acs.orglett.0c00199<\/a>.<\/p>\n

(f) J. Qin, S. Zhu, L. Chu, Organometallics<\/em> 2021<\/strong>, 40<\/em>, 2246. doi: 10.1021\/acs.organomet.0c00813<\/a>.<\/p>\n

(g) S. Xu, F. Sun, W. Deng, H. Hao, X. Duan, New J. Chem.<\/em> 2018<\/strong>, 42<\/em>, 16464. doi: 10.1039\/C8NJ02184H<\/a>.<\/p>\n

(h) L. Liao, X. Kong, X. Duan, J. Org. Chem. <\/em>2014<\/strong>, 79<\/em>, 777. doi: 10.1021\/jo402084m<\/a>.<\/p>\n

(i) T. Wu, Y. Zhang, Y. Fu, F. Liu, J. Tang, P. Liu, F. D. Toste, B. Ye, Chem. <\/em>2021<\/strong>, 7<\/em>, 1963. doi: 10.1016\/j.chempr.2021.06.007<\/a>.<\/p>\n

(j) L. K. G. Ackerman, M. M. Lovell, D. J. Weix, Nature<\/em> 2015<\/strong>, 524<\/em>, 454. doi: 10.1038\/nature14676.<\/a><\/p>\n[10] (a) L. Huang, L. K. G. Ackerman, K. Kang, A. M. Parsons, D. J. Weix, J. Am. Chem. Soc. <\/em>2019<\/strong>, 141<\/em>, 10978. doi: 10.1021\/jacs.9b05461<\/a>.<\/p>\n

(b) K. Kang, L. Huang, D. J. Weix, J. Am. Chem. Soc. <\/em>2020<\/strong>, 142<\/em>, 10634. doi: 10.1021\/jacs.0c04670<\/a>.<\/p>\n

\u672c\u6587\u7248\u6743\u5c5e\u4e8e\u00a0Chem-Station\u5316\u5b66\u7a7a\u95f4\uff0c \u6b22\u8fce\u70b9\u51fb\u6309\u94ae\u5206\u4eab\uff0c\u672a\u7ecf\u8bb8\u53ef\uff0c\u8c22\u7edd\u8f6c\u8f7d<\/p>\n","protected":false},"excerpt":{"rendered":"\u672c\u6587\u4f5c\u8005\uff1a\u6749\u6749 \u5bfc\u8bfb \u8fd1\u65e5\uff0cWisconsin-Madison\u5927\u5b66\u7684D. J. Weix\u8bfe\u9898\u7ec4\u5728J. Am. Chem. Soc.\u4e2d\u53d1\u8868\u8bba\u6587\uff0c\u62a5\u9053\u4e00\u79cd\u5168\u65b0\u7684\u901a\u8fc7Ni\u4e0ePd\u50ac\u5316\u7684\u6742\u82b3\u57fa\u5364\u4e0e\u6742\u82b3\u57fa\u4e09\u6c1f\u7532\u78fa\u9178\u916f\u4e4b\u95f4\u7684\u591a\u91d1\u5c5e\u4ea4\u53c9Ullmann\u5076\u8054\u53cd\u5e94 (multimetallic cross-Ullmann coupling)\u65b9\u6cd5\u5b66\uff0c\u8fdb\u800c\u6210\u529f\u5b8c\u6210\u4e00\u7cfb\u5217\u6742\u73af\u8054\u82b3\u57fa\u5316\u5408\u7269 (biheteroaryl)\u7684\u6784\u5efa\u3002\u8fd9\u4e00\u5168\u65b0\u7684\u4ea4\u53c9\u5076\u8054\u7b56\u7565\u5177\u6709\u53cd\u5e94\u6761\u4ef6\u6e29\u548c\u3001\u5e95\u7269\u8303\u56f4\u5e7f\u6cdb\u4ee5\u53ca\u9ad8\u5ea6\u7684\u5b98\u80fd\u56e2\u517c\u5bb9\u6027\u7b49\u4f18\u52bf\u3002 A General, Multimetallic Cross-Ullmann Biheteroaryl Synthesis from Heteroaryl Halides and Heteroaryl Triflates K. Kang, N. L. Loud, T. A. DiBenedetto, D. J. Weix, J. Am. Chem. Soc.\u00a02021, 143, 21484. doi:10.1021\/jacs.1c10907. \u6b63\u6587 \u6742\u73af\u8054\u82b3\u57fa\u5316\u5408\u7269\u5e7f\u6cdb\u5b58\u5728\u4e8e\u5404\u7c7b\u836f\u7269\u3001\u7535\u5b50\u6750\u6599\u3001\u914d\u4f53\u4ee5\u53ca\u5929\u7136\u4ea7\u7269\u5206\u5b50\u4e2d\u3002\u7136\u800c\uff0c\u5bf9\u4e8e\u6742\u73af\u8054\u82b3\u57fa\u5316\u5408\u7269\u76f8\u5173\u5408\u6210\u7b56\u7565\u7684\u7814\u7a76\uff0c\u76ee\u524d\u4ecd\u9762\u4e34\u8bf8\u591a\u6311\u6218(Scheme 1)[1]-[8]\u3002\u53d7\u5230\u524d\u671f\u5bf9\u4e8e\u4ea4\u53c9Ullmann\u5076\u8054\u53cd\u5e94\u65b9\u6cd5\u5b66[9]\u4ee5\u53ca\u672c\u8bfe\u9898\u7ec4\u5bf9\u4e8e\u591a\u91d1\u5c5e\u50ac\u5316\u7684\u4ea4\u53c9\u5076\u8054\u53cd\u5e94\u65b9\u6cd5\u5b66[10]\u76f8\u5173\u7814\u7a76\u7684\u542f\u53d1\uff0c\u8fd9\u91cc\uff0cD. J. Weix\u8bfe\u9898\u7ec4\u6210\u529f\u8bbe\u8ba1\u51fa\u4e00\u79cd\u5168\u65b0\u7684\u591a\u91d1\u5c5e\u50ac\u5316\u4ea4\u53c9Ullmann\u5076\u8054\u53cd\u5e94\u65b9\u6cd5\u5b66 (Scheme 1)\u3002 \u9996\u5148\uff0c\u4f5c\u8005\u91c7\u75281a\u4e0e3-\u6eb4\u5421\u55762a\u4f5c\u4e3a\u6a21\u578b\u5e95\u7269\uff0c\u8fdb\u884c\u76f8\u5173\u5076\u8054\u53cd\u5e94\u6761\u4ef6\u7684\u4f18\u5316\u7b5b\u9009 (Table 1)\u3002\u8fdb\u800c\u786e\u5b9a\u6700\u4f73\u7684\u53cd\u5e94\u6761\u4ef6\u4e3a\uff1a\u91c7\u7528NiBr2(dme)\/N1\u4e0ePdCl2\/P1\u4f5c\u4e3a\u50ac\u5316\u5242\uff0cZn\u4f5c\u4e3a\u8fd8\u539f\u5242\uff0c\u65e0\u6c34KBr\u4f5c\u4e3a\u6dfb\u52a0\u5242\uff0cDMF\u4f5c\u4e3a\u53cd\u5e94\u6eb6\u5242\uff0c\u53cd\u5e94\u6e29\u5ea6\u4e3a60oC\uff0c\u6700\u7ec8\u83b7\u5f9779%\u6536\u7387\u7684\u5076\u8054\u4ea7\u72693a\u3002 \u5728\u4e0a\u8ff0\u7684\u6700\u4f73\u53cd\u5e94\u6761\u4ef6\u4e0b\uff0c\u4f5c\u8005\u9996\u5148\u5bf9\u5404\u7c7b\u6742\u82b3\u57fa\u6eb4\u4e0e\u6742\u82b3\u57fa\u6c2f\u5e95\u7269\u7684\u5e94\u7528\u8303\u56f4\u8fdb\u884c\u8003\u5bdf (Scheme 2)\u3002\u7814\u7a76\u8868\u660e\uff0c\u4e00\u7cfb\u5217\u516d\u5143\u73af\u3001\u4e94\u5143\u73af\u4e0e\u7a20\u5408\u6742\u73af\u82b3\u57fa\u6eb4\u5e95\u7269\uff0c\u5747\u80fd\u591f\u8f83\u597d\u5730\u4e0e\u4e0a\u8ff0\u7684\u6807\u51c6\u53cd\u5e94\u6761\u4ef6\u517c\u5bb9\uff0c\u5e76\u4ee5\u4e2d\u7b49\u81f3\u4f18\u826f\u7684\u53cd\u5e94\u6536\u7387\uff0c\u83b7\u5f97\u76f8\u5e94\u7684\u4ea4\u53c9\u5076\u8054\u4ea7\u72693a–3z\u4ee5\u53ca3aa-3aj\u3002\u4e4b\u540e\uff0c\u4f5c\u8005\u53d1\u73b0\uff0c\u4e00\u7cfb\u5217\u6742\u82b3\u57fa\u6c2f\u5e95\u7269\uff0c\u540c\u6837\u80fd\u591f\u6709\u6548\u5730\u53c2\u4e0e\u4e0a\u8ff0\u7684\u4ea4\u53c9\u5076\u8054\u8fc7\u7a0b\uff0c\u8fdb\u800c\u4ee5\u4e2d\u7b49\u81f3\u4f18\u826f\u7684\u53cd\u5e94\u6536\u7387\uff0c\u83b7\u5f97\u76f8\u5e94\u7684\u76ee\u6807\u4ea7\u72693ak–3at\u3002\u5e76\u4e14\uff0c\u901a\u8fc7\u6742\u82b3\u57fa\u6c2f\u5e95\u7269\u53c2\u4e0e\u7684\u4ea4\u53c9Ullmann\u5076\u8054\u53cd\u5e94\u65b9\u6cd5\u5b66\u80fd\u591f\u8fdb\u4e00\u6b65\u5e94\u7528\u4e8e\u5404\u7c7b\u836f\u7269\u5206\u5b50 (3as-3at)\u7684\u7ed3\u6784\u4fee\u9970\u3002\u800c\u4e14\uff0c\u4f5c\u8005\u8fdb\u4e00\u6b65\u53d1\u73b0\uff0c\u5c06\u5e95\u72693ao\u7684\u7528\u91cf\u589e\u52a0\u81f35 mmol\u65f6\uff0c\u540c\u6837\u80fd\u591f\u987a\u5229\u5730\u5b8c\u6210\u4e0a\u8ff0\u7684\u4ea4\u53c9\u5076\u8054\u8fc7\u7a0b\u3002\u540c\u65f6\uff0c\u8be5\u5c0f\u7ec4\u89c2\u5bdf\u5230\uff0c\u8fd9\u4e00\u5168\u65b0\u7684\u4ea4\u53c9Ullmann\u5076\u8054\u7b56\u7565\u5bf9\u4e8e\u5404\u7c7b\u4eb2\u7535\u6027\u5b98\u80fd\u56e2 (3g, 3h, 3p, 3q, 3an, 3ao)\u3001\u9178\u654f\u6027\u4fdd\u62a4\u57fa (acid-sensitive protecting groups) (3m, 3s, 3t, 3x, 3ah) \u4e0e\u70ef\u4e19\u57fa (3ag)\u4ee5\u53ca\u5177\u6709\u9ad8\u5ea6\u7acb\u4f53\u4f4d\u963b\u7684\u5404\u7c7b\u57fa\u56e2 (3e, 3o, 3u, 3w,3xaa, 3ac, 3ae)\uff0c\u5747\u8868\u73b0\u51fa\u826f\u597d\u7684\u517c\u5bb9\u6027\u3002\u63a5\u4e0b\u6765\uff0c\u8be5\u5c0f\u7ec4\u7814\u7a76\u53d1\u73b0\uff0c\u91c7\u7528ttbtpy (N3)\u914d\u4f53\u65f6\u00a0 (Conditions B)\uff0c\u80fd\u591f\u6709\u6548\u5730\u6291\u5236\u7f3a\u7535\u5b50\u6742\u82b3\u57fa\u6eb4\u5e95\u7269\u7684\u540c\u5076\u8054\u8fc7\u7a0b\uff0c\u8fdb\u800c\u83b7\u5f97\u76f8\u5e94\u7684\u4ea4\u53c9Ullmann\u5076\u8054\u4ea7\u72693f–3j\u3002 \u63a5\u4e0b\u6765\uff0c\u4f5c\u8005\u5bf9\u4e00\u7cfb\u5217\u6742\u82b3\u57fa\u4e09\u6c1f\u7532\u78fa\u9178\u916f\u5e95\u7269\u7684\u5e94\u7528\u8303\u56f4\u8fdb\u884c\u6df1\u5165\u7814\u7a76(Scheme 3)\u3002\u8be5\u5c0f\u7ec4\u53d1\u73b0\uff0c\u5404\u7c7b\u5177\u6709\u4e0d\u540c\u7535\u5b50\u6027\u8d28\u7684\u6742\u82b3\u57fa\u4e09\u6c1f\u7532\u78fa\u9178\u916f\u5e95\u7269\uff0c\u5747\u80fd\u591f\u987a\u5229\u5730\u53c2\u4e0e\u4e0a\u8ff0\u7684\u4ea4\u53c9Ullmann\u5076\u8054\u8fc7\u7a0b\uff0c\u5e76\u4ee5\u4e2d\u7b49\u81f3\u4f18\u826f\u7684\u53cd\u5e94\u6536\u7387\uff0c\u83b7\u5f97\u76f8\u5e94\u7684\u4ea7\u72693au–3aai\u3002\u540c\u65f6\uff0c\u7814\u7a76\u8868\u660e\uff0c\u4e0a\u8ff0\u7684\u6807\u51c6\u53cd\u5e94\u4f53\u7cfb\u540c\u6837\u80fd\u591f\u826f\u597d\u5730\u5e94\u7528\u4e8e\u5404\u7c7b\u975e\u82b3\u9999\u70ef\u57fa\u4e09\u6c1f\u7532\u78fa\u9178\u916f (3aaj)\u5e95\u7269\uff0c\u8fdb\u800c\u83b7\u5f97\u826f\u597d\u7684\u53cd\u5e94\u6536\u7387\u3002 \u63a5\u4e0b\u6765\uff0c\u4f5c\u8005\u901a\u8fc7\u6807\u51c6\u7684\u9ad8\u901a\u91cf\u5b9e\u9a8c (THE, high-throughput experimentation)\u5bf9\u4e0a\u8ff0\u7684\u53cd\u5e94\u6761\u4ef6\u8fdb\u884c\u8fdb\u4e00\u6b65\u4f18\u5316\uff0c\u540c\u65f6\u5bf9\u8fd9\u4e00\u5168\u65b0\u7684\u4ea4\u53c9Ullmann\u5076\u8054\u53cd\u5e94\u7b56\u7565\u5728\u836f\u7269\u5316\u5b66\u4e2d\u7684\u5e94\u7528\u8fdb\u884c\u66f4\u4e3a\u6df1\u5165\u7684\u7814\u7a76 (Figure 1)\u3002 \u603b\u7ed3 Wisconsin-Madison\u5927\u5b66\u7684D. J. Weix\u8bfe\u9898\u7ec4\u62a5\u9053\u4e00\u79cd\u5168\u65b0\u7684\u901a\u8fc7Ni\u4e0ePd\u50ac\u5316\u5242\u4fc3\u8fdb\u7684\u6742\u82b3\u57fa\u5364\u4e0e\u6742\u82b3\u57fa\u4e09\u6c1f\u7532\u78fa\u9178\u916f\u4e4b\u95f4\u7684\u591a\u91d1\u5c5e\u4ea4\u53c9Ullmann\u5076\u8054\u53cd\u5e94 (multimetallic cross-Ullmann coupling)\u65b9\u6cd5\u5b66\uff0c\u8fdb\u800c\u987a\u5229\u5b8c\u6210\u4e00\u7cfb\u5217\u6742\u73af\u8054\u82b3\u5206\u5b50\u7684\u6784\u5efa\u3002\u8fd9\u4e00\u5168\u65b0\u7684\u4ea4\u53c9Ullmann\u5076\u8054\u53cd\u5e94\u65b9\u6cd5\u5b66\u5177\u6709\u53cd\u5e94\u6761\u4ef6\u6e29\u548c\u3001\u5e95\u7269\u8303\u56f4\u5e7f\u6cdb\u4ee5\u53ca\u9ad8\u5ea6\u7684\u5b98\u80fd\u56e2\u517c\u5bb9\u6027\u7b49\u4f18\u52bf\u3002\u540c\u65f6\u8be5\u5c0f\u7ec4\u901a\u8fc7\u9ad8\u901a\u91cf\u5b9e\u9a8c\u7684\u8fdb\u4e00\u6b65\u4f18\u5316\uff0c\u8fdb\u4e00\u6b65\u8868\u660e\u8fd9\u4e00\u5168\u65b0\u7684\u4ea4\u53c9Ullmann\u5076\u8054\u5177\u6709\u6f5c\u5728\u7684\u5408\u6210\u5e94\u7528\u4ef7\u503c\u3002 \u53c2\u8003\u6587\u732e [1] (a) V. F. Slagt, A. H. M. de Vries, J. 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