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镍催化的三氟甲基烯烃的自由基促进脱氟烷基硼化反应以制备β-二氟高烯丙基硼酸酯。

Ni-Catalyzed Radical-Promoted Defluoroalkylborylation of Trifluoromethyl Alkenes To Access -Difluorohomoallylic Boronates.

作者信息

Qiu Jian, Wang Cece, Zhou Lu, Lou Yixian, Yang Kai, Song Qiuling

机构信息

Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, Fuzhou University, Fuzhou, Fujian 350108, People's Republic of China.

Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou, Zhejiang 310014, People's Republic of China.

出版信息

Org Lett. 2022 Apr 1;24(12):2446-2451. doi: 10.1021/acs.orglett.2c00800. Epub 2022 Mar 21.

Abstract

-Difluoroalkenyl boronates are attractive synthons for constructing diverse -difluoroalkenes and organoboron compounds. However, the strategies for the construction of -difluorohomoallyl boronates has scarcely been described. Herein, we develop an efficient protocol for the construction of -difluorohomoallylic boronates through a Ni-catalyzed radical-promoted defluoroalkylborylation of α-trifluoromethyl alkenes with α-haloboronates under mild conditions. This reaction features a broad substrate scope with good functional group tolerance and diverse transformations.

摘要

-二氟烯基硼酸酯是构建各种二氟烯烃和有机硼化合物的有吸引力的合成子。然而,关于构建二氟高烯丙基硼酸酯的策略却鲜有报道。在此,我们开发了一种高效的方法,通过镍催化的α-三氟甲基烯烃与α-卤代硼酸酯在温和条件下的自由基促进脱氟烷基硼化反应来构建二氟高烯丙基硼酸酯。该反应具有广泛的底物范围、良好的官能团耐受性和多样的转化反应。

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