Figure 1 | General hydroboration followed by oxidation of alkenes gives alcohols<\/p>\n \u5728\u5b9e\u9645\u64cd\u4f5c\u4e2d\u9700\u8981\u6ce8\u610f\u4ee5\u4e0b\uff1a<\/p>\n RCO2<\/sub>H>\u70ef>RCHO>RCOR\u2019>RCN>\u73af\u6c27\u5316\u7269>RCO2<\/sub>R\u2019<\/p>\n \u603b\u7684\u6765\u770b\uff0c\u787c\u6c22\u5316\/\u6c27\u5316\u53cd\u5e94\u6700\u7ec8\u5f97\u5230\u7684\u662f\u53cdMarkovnikov\u89c4\u5219\uff08\u4e0b\u79f0\u9a6c\u6c0f\u89c4\u5219\uff09\u7684\u4ea7\u7269\uff0c\u5373\u4ea7\u7269\u4e3a\u8f83\u5c11\u53d6\u4ee3\u57fa\u7684\u9187\uff0c\u5e76\u4e14\u53d1\u751f\u7684\u662f\u987a\u5f0f\u52a0\u6210(cis<\/em>-addn.)\u3002\u540c\u65f6\uff0c\u4f4d\u963b\u8f83\u5c0f\u7684\u787c\u70f7\u53ef\u4ee5\u53d1\u751f\u4e09\u6b21\u787c\u6c22\u5316\u52a0\u6210\u53cd\u5e94\u76f4\u5230\u787c\u70f7\u4e2d\u6c22\u539f\u5b50\u6d88\u8017\u5b8c\u5168\u3002<\/p>\n \u5f53\u7535\u5b50\u6548\u5e94\u7684\u4f5c\u7528\u4e0d\u5927\u65f6\uff0c\u4f4d\u963b\u6210\u4e3a\u4e86\u53cd\u5e94\u533a\u57df\u9009\u62e9\u6027\u7684\u4e3b\u8981\u4f5c\u7528\uff0c\u787c\u4f1a\u4f18\u5148\u52a0\u6210\u5230\u4f4d\u963b\u8f83\u5c0f\u7684\u78b3\u539f\u5b50\u4e0a\uff1a<\/p>\n Figure 2 | Regioselectivity of bydroboration contributed by hindrance<\/p>\n \u4e3a\u4e86\u5b9e\u73b0\u4e00\u4e9b\u53cd\u5e94\u7684\u533a\u57df\u9009\u62e9\u6027\u3001\u7acb\u4f53\u9009\u62e9\u6027\u548c\/\u6216\u5316\u5b66\u9009\u62e9\u6027\uff0c\u4e4b\u540e\u7684\u7814\u7a76\u5f00\u53d1\u4e86\u4e00\u4e0b\u4e00\u4e9b\u787c\u70f7\u8bd5\u5242\uff1a<\/p>\n Figure 3 | Boranes with special alkyl groups<\/p>\n Example\uff1a<\/p>\n Scheme 1<\/p>\n \u800c\u5728\u8fd9\u4e2a\u53cd\u5e94\u4e2d\uff0c\u82e5\u662f\u4ee5BH3\/THF\u5904\u7406\uff0c\u5219\u4f1a\u5f97\u5230\u51e0\u4e4e\u4e3a1\uff1a1\u7684\u5f02\u6784\u4f53<\/p>\n \uff081\uff09\u901a\u8fc7\u987a\u5f0f\u7684\u56db\u5143\u73af\u8fc7\u6e21\u6001\uff0c\u787c\u70f7\u5c06\u81ea\u8eab\u52a0\u6210\u5230\u53cc\u952e\u4e0a\u3002\u56e0\u4e3aB-H\u662f\u9ad8\u5ea6\u6781\u5316\u7684\uff0c\u5e76\u4e14\u787c\u539f\u5b50\u4e0a\u5e26\u6709\u6b63\u70b9\uff0c\u56e0\u6b64\u4f1a\u5bfc\u5411\u5230\u8f83\u591a\u53d6\u4ee3\u7684\u78b3\u539f\u5b50\u4e0a\uff1a<\/p>\n Figure 4 | 4-membered ring transition state of borane and alkene, regioselectivity and some examples(EWG=electron withdrawing group , EDG=electron donating group).<\/p>\n \uff082\uff09\u6c27\u5316\u8fc7\u7a0b Scheme 2 | Mechanism of oxidation step(formation of alcohols)<\/p>\n b.\u751f\u6210\u5364\u5316\u7269\u548c\u80fa<\/p>\n \u5f53\u7528Br2<\/sub>\u6216I2<\/sub>\u8fdb\u884c\u6c27\u5316\u65f6\uff0c\u53ef\u4ee5\u5f97\u5230\u6eb4\u4ee3\u70c3\u6216\u7898\u4ee3\u70c3\uff1b<\/p>\n \u82e5\u4f7f\u7528ClOSO3<\/sub>H\u6216NH2<\/sub>Cl\u6c27\u5316\uff0c\u5219\u4f1a\u5f97\u5230\u4f2f\u80fa(Sch. 3-A)\uff0c\u4e00\u822c\u6765\u8bf4\u80fa\u7684\u5408\u6210\u5f88\u56f0\u96be\u5e76\u4e14\u9700\u8981\u4eb2\u7535\u7684\u787c\u539f\u5b50\uff08\u787c\u9178\u548c\u787c\u9178\u916f\u6bd4\u8f83\u60f0\u6027\uff09\uff1b\u5f53\u4f7f\u7528HBCl2\u8fdb\u884c\u787c\u6c22\u5316\u518d\u7528\u53e0\u6c2e\u5316\u5408\u7269\u53cd\u5e94\u662f\uff0c\u5c31\u4f1a\u5f97\u5230\u4ef2\u80fa(Sch. 3-B)\u3002<\/p>\n Scheme 3 | Mechanism of oxidation step(formation of amines)<\/p>\n Examples\uff1a<\/p>\n (1)<\/p>\n Scheme 4 | Convert alkyne to ketone\/aldehyde by hydroboration-oxidation<\/p>\n <\/p>\n Sia2<\/sub>BH\u53ea\u4f1a\u548c\u7094\u53d1\u751f\u4e00\u6b21\u787c\u6c22\u5316\u53cd\u5e94\u5f97\u5230\u787c\u9178\u70ef\u9187\u916f\uff0c\u6c27\u5316\u540e\u5f97\u5230\u916e<\/p>\n (2)<\/p>\n Scheme 5 | Steric and electronic control with alkenes(J. Org. Chem. <\/em>1983, 48, 644, DOI:10.1021\/jo00153a004)<\/p>\n (3)<\/p>\n Scheme 6 | Examples of formation of amine<\/p>\n \u4e3a\u4e86\u63a7\u5236\u53cd\u5e94\u7684\u7acb\u4f53\u9009\u62e9\u6027\uff0c\u56e0\u6b64\u5f00\u53d1\u4e86\u4e00\u4e9b\u5177\u6709\u7279\u6b8a\u7ed3\u6784\u6216\u5177\u6709\u7279\u6b8a\u4f4d\u963b\u7684\u787c\u70f7\u8fdb\u884c\u53cd\u5e94\uff0c\u4f8b\u5982\uff1a<\/p>\n (1)<\/p>\n Scheme 7 | A stereoselective hydroboration that can be explained by Houl\u2019s model<\/p>\n (2)<\/p>\n Scheme 8 | Another example and explanation illustrated by Houl\u2019s model<\/p>\n \u8fd9\u4e2a\u53cd\u5e94\u4e2d\uff0c\u56e0\u4e3a\u70ef\u4e19\u57fa\u7ed3\u6784\u7247\u6bb5\u7684\u5b58\u5728\u4f7f\u5f97\u6784\u8c61\u53d1\u751f\u7279\u6b8a\u6392\u5217\uff0c\u56e0\u6b64\u787c\u70f7\u4ece\u4f4d\u963b\u6700\u5c0f\u7684\u4e00\u4fa7\u8fdb\u653b\u8fdb\u884c\u52a0\u6210\u53cd\u5e94\uff0c\u5f97\u5230\u7acb\u4f53\u4e13\u4e00\u8f83\u9ad8\u7684\u4ea7\u7269\u3002<\/p>\n (3)<\/p>\n Scheme 9 | Interactional hydroborations<\/p>\n \u7b2c\u4e00\u6b21\u787c\u6c22\u5316\u53cd\u5e94\u7684\u4e2d\u95f4\u4f53\u53ef\u4ee5\u8fdb\u884c\u5206\u5b50\u5185\u787c\u6c22\u5316\uff0c\u4f46\u662f\u7531\u4e8e\u5206\u5b50\u94fe\u7684\u539f\u56e0\u5f97\u5230\u7acb\u4f53\u4e13\u4e00\u7684\u4ea7\u7269\u3002<\/p>\n \uff081\uff09<\/p>\n Scheme 10 | Annulation and formation of cyclic ketone promoted by hudroboration and CO work-up<\/p>\n Scheme 11 | Mechanism of annulations by CO work-up<\/p>\n <\/p>\n![\"\"](\"https:\/\/assets.www.gsbet888.com\/uploads\/2017\/10\/1-4.png\")
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<\/a><\/p>\n<\/a><\/p>\n<\/a><\/p>\n2.\u53cd\u5e94\u673a\u7406<\/strong>\uff1a<\/h4>\n
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\na.\u9187\u7684\u751f\u6210<\/p>\n<\/a><\/p>\n<\/a><\/p>\n<\/a><\/p>\n<\/a><\/p>\n<\/a><\/p>\n3.\u7acb\u4f53\u4e13\u4e00\u6027\u7684\u63a7\u5236<\/strong><\/h4>\n
<\/a><\/p>\n<\/a><\/p>\n<\/a><\/p>\n4.\u5176\u4ed6<\/strong><\/h4>\n
<\/a><\/p>\n\u53cd\u5e94\u673a\u7406\uff1a<\/strong><\/h4>\n
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