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

School of Chemistry and Moleculai Engineering

Nanjing Tech University

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

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.

Original language	English
Pages (from-to)	5995-6000
Number of pages	6
Journal	Organic Letters
Volume	25
Issue number	32
DOIs	https://doi.org/10.1021/acs.orglett.3c02102
State	Published - 18 Aug 2023

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title = "Ni-Catalyzed Reductive Dibenzylation of Trifluoromethylalkenes for CF3-Containing All-Carbon Quaternary Center Construction",

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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T1 - Ni-Catalyzed Reductive Dibenzylation of Trifluoromethylalkenes for CF3-Containing All-Carbon Quaternary Center Construction

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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U2 - 10.1021/acs.orglett.3c02102

DO - 10.1021/acs.orglett.3c02102

M3 - 文章

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AN - SCOPUS:85168234258

SN - 1523-7060

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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

Abstract

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