S N2′ Defluorinative Allylation of Trifluoromethylalkenes with Allylsilanes

Meng Meng Sun; Haidong Liu; Chuan Zhu; Chao Feng

doi:10.1055/a-1653-2685

S _N2′ Defluorinative Allylation of Trifluoromethylalkenes with Allylsilanes

Meng Meng Sun, Haidong Liu, Chuan Zhu, Chao Feng

School of Chemistry and Moleculai Engineering

Nanjing Tech University

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

4 Scopus citations

Abstract

An SN2? defluorinative allylation of trifluoromethylalkenes with readily available allylsilanes to access homoallyl gem-difluoroalkenes is reported. The reaction is triggered by a catalytic amount of TBAF, with the extruded fluoride in the reaction serving as a sustainable activator for organosilanes. The high efficiency, good functional group tolerance, and mild reaction conditions underline the potential of this method in synthetic chemistry.

Original language	English
Article number	ss-2021-z1520-fa
Pages (from-to)	1108-1114
Number of pages	7
Journal	Synthesis (Germany)
Volume	54
Issue number	4
DOIs	https://doi.org/10.1055/a-1653-2685
State	Published - 11 Nov 2021

Keywords

C-F bond cleavage
allylation
allylsilane
gem-difluoroalkene
trifluoromethylalkene

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10.1055/a-1653-2685

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title = "S N2′ Defluorinative Allylation of Trifluoromethylalkenes with Allylsilanes",

abstract = "An SN2? defluorinative allylation of trifluoromethylalkenes with readily available allylsilanes to access homoallyl gem-difluoroalkenes is reported. The reaction is triggered by a catalytic amount of TBAF, with the extruded fluoride in the reaction serving as a sustainable activator for organosilanes. The high efficiency, good functional group tolerance, and mild reaction conditions underline the potential of this method in synthetic chemistry.",

keywords = "C-F bond cleavage, allylation, allylsilane, gem-difluoroalkene, trifluoromethylalkene",

author = "Sun, {Meng Meng} and Haidong Liu and Chuan Zhu and Chao Feng",

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T1 - S N2′ Defluorinative Allylation of Trifluoromethylalkenes with Allylsilanes

AU - Sun, Meng Meng

AU - Liu, Haidong

AU - Zhu, Chuan

AU - Feng, Chao

PY - 2021/11/11

Y1 - 2021/11/11

N2 - An SN2? defluorinative allylation of trifluoromethylalkenes with readily available allylsilanes to access homoallyl gem-difluoroalkenes is reported. The reaction is triggered by a catalytic amount of TBAF, with the extruded fluoride in the reaction serving as a sustainable activator for organosilanes. The high efficiency, good functional group tolerance, and mild reaction conditions underline the potential of this method in synthetic chemistry.

AB - An SN2? defluorinative allylation of trifluoromethylalkenes with readily available allylsilanes to access homoallyl gem-difluoroalkenes is reported. The reaction is triggered by a catalytic amount of TBAF, with the extruded fluoride in the reaction serving as a sustainable activator for organosilanes. The high efficiency, good functional group tolerance, and mild reaction conditions underline the potential of this method in synthetic chemistry.

KW - C-F bond cleavage

KW - allylation

KW - allylsilane

KW - gem-difluoroalkene

KW - trifluoromethylalkene

UR - http://www.scopus.com/inward/record.url?scp=85119514369&partnerID=8YFLogxK

U2 - 10.1055/a-1653-2685

DO - 10.1055/a-1653-2685

M3 - 文章

AN - SCOPUS:85119514369

SN - 0039-7881

VL - 54

SP - 1108

EP - 1114

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 4

M1 - ss-2021-z1520-fa

ER -

S _N2′ Defluorinative Allylation of Trifluoromethylalkenes with Allylsilanes

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Keywords

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