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Enantioselective Copper-Catalyzed sp2/sp3 Diborylation of 1-Chloro-1-Trifluoromethylalkenes
ACS Central Science ( IF 18.2 ) Pub Date : 2022-07-20 , DOI: 10.1021/acscentsci.2c00339
Zhenwei Fan 1 , Mingxing Ye 1 , Yahao Wang 1 , Jian Qiu 1 , Wangyang Li 1 , Xingxing Ma 1 , Kai Yang 1 , Qiuling Song 1, 2, 3
Affiliation  

Fluorine-containing organoboron compounds have emerged as novel building blocks in chemical synthesis; among them, fluorinated sp2/sp3 diborylated compounds are particularly appealing, since they might undergo chemoselective and diversified transformations of different C–B bonds with fluorinated functionality, thus bringing versatility and complexity to the eventual products. However, expedient, synthetic strategies for the construction of such fluorinated diborylative compounds are very sparse. Herein, we disclose enantioselective Cu-catalyzed sp2/sp3 diborylations of 1-chloro-1-trifluoromethylalkenes, leading to diborylated compounds bearing a gem-difluoroalkenyl moiety; most intriguingly, the new formed C–B bonds include one stereoselective and optically pure Csp3–B bond. Further transformations on the eventual products demonstrated the values of our presented strategy.

中文翻译:

1-Chloro-1-Trifluoromethylalkenes 的对映选择性铜催化 sp2/sp3 二硼化

含氟有机硼化合物已成为化学合成中的新型构件;其中,氟化的sp 2 /sp 3二硼化合物尤其具有吸引力,因为它们可以对具有氟化官能团的不同C-B键进行化学选择性和多样化的转化,从而为最终产品带来多功能性和复杂性。然而,用于构建这种氟化二硼化合物的权宜之计合成策略非常稀少。在此,我们公开了 1-氯-1-三氟甲基烯烃的对映选择性 Cu 催化的 sp 2 /sp 3二硼化,导致二硼化化合物带有宝石-二氟烯基部分;最有趣的是,新形成的 C-B 键包括一个立体选择性和光学纯的 Csp 3 -B 键。对最终产品的进一步改造证明了我们提出的战略的价值。
更新日期:2022-07-20
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