Ni-Catalyzed Reductive Dibenzylation of Trifluoromethylalkenes for CF3-Containing All-Carbon Quaternary Center Construction

Kai Chen; Qian Liu; Jinyan Wan; Chuan Zhu; Chao Feng

doi:10.1021/acs.orglett.3c02102

Ni-Catalyzed Reductive Dibenzylation of Trifluoromethylalkenes for CF₃-Containing All-Carbon Quaternary Center Construction

Kai Chen, Qian Liu, Jinyan Wan, Chuan Zhu, Chao Feng

化学与分子工程学院

Nanjing Tech University

科研成果: 期刊稿件 › 文章 › 同行评审

9 引用（Scopus）

摘要

A Ni-catalyzed reductive dicarbofunctionalization of α-CF₃ styrenes with benzyl bromides has been accomplished. This transformation obviates the commonly facile β-F elimination effectively and enables the creation of CF₃-substituted all-carbon quaternary centers of pharmaceutical interests. Preliminary mechanistic studies suggest a pathway consisting of benzyl radical addition and subsequent nickel-mediated benzylation of the resulting α-CF₃-embedded tertiary C radical.

源语言	英语
页（从-至）	5995-6000
页数	6
期刊	Organic Letters
卷	25
期	32
DOI	https://doi.org/10.1021/acs.orglett.3c02102
出版状态	已出版 - 18 8月 2023

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10.1021/acs.orglett.3c02102

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abstract = "A Ni-catalyzed reductive dicarbofunctionalization of α-CF3 styrenes with benzyl bromides has been accomplished. This transformation obviates the commonly facile β-F elimination effectively and enables the creation of CF3-substituted all-carbon quaternary centers of pharmaceutical interests. Preliminary mechanistic studies suggest a pathway consisting of benzyl radical addition and subsequent nickel-mediated benzylation of the resulting α-CF3-embedded tertiary C radical.",

author = "Kai Chen and Qian Liu and Jinyan Wan and Chuan Zhu and Chao Feng",

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AU - Chen, Kai

AU - Liu, Qian

AU - Wan, Jinyan

AU - Zhu, Chuan

AU - Feng, Chao

PY - 2023/8/18

Y1 - 2023/8/18

N2 - A Ni-catalyzed reductive dicarbofunctionalization of α-CF3 styrenes with benzyl bromides has been accomplished. This transformation obviates the commonly facile β-F elimination effectively and enables the creation of CF3-substituted all-carbon quaternary centers of pharmaceutical interests. Preliminary mechanistic studies suggest a pathway consisting of benzyl radical addition and subsequent nickel-mediated benzylation of the resulting α-CF3-embedded tertiary C radical.

AB - A Ni-catalyzed reductive dicarbofunctionalization of α-CF3 styrenes with benzyl bromides has been accomplished. This transformation obviates the commonly facile β-F elimination effectively and enables the creation of CF3-substituted all-carbon quaternary centers of pharmaceutical interests. Preliminary mechanistic studies suggest a pathway consisting of benzyl radical addition and subsequent nickel-mediated benzylation of the resulting α-CF3-embedded tertiary C radical.

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DO - 10.1021/acs.orglett.3c02102

M3 - 文章

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AN - SCOPUS:85168234258

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JO - Organic Letters

JF - Organic Letters

IS - 32

ER -

Ni-Catalyzed Reductive Dibenzylation of Trifluoromethylalkenes for CF3-Containing All-Carbon Quaternary Center Construction

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Ni-Catalyzed Reductive Dibenzylation of Trifluoromethylalkenes for CF₃-Containing All-Carbon Quaternary Center Construction