Copper-catalyzed one-pot trifluoromethylation/aryl migration/carbonyl formation with homopropargylic alcohols

Pin Gao; Yong Wen Shen; Ran Fang; Xin Hua Hao; Zi Hang Qiu; Fan Yang; Xiao Biao Yan; Qiang Wang; Xiang Jun Gong; Xue Yuan Liu; Yong Min Liang

doi:10.1002/anie.201403383

Copper-catalyzed one-pot trifluoromethylation/aryl migration/carbonyl formation with homopropargylic alcohols

Pin Gao
, Yong Wen Shen
, Ran Fang
, Xin Hua Hao
, Zi Hang Qiu
, Fan Yang
, Xiao Biao Yan
, Qiang Wang
, Xiang Jun Gong
, Xue Yuan Liu
, Yong Min Liang

Lanzhou University

科研成果: 期刊稿件 › 文章 › 同行评审

144 引用（Scopus）

摘要

A novel copper-catalyzed one-pot functionalization of homopropargylic alcohols that involves trifluoromethylation, aryl migration, and formation of a carbonyl moiety has been developed. This reaction constitutes the first direct conversion of homopropargylic alcohols into CF₃-containing 3-butenal or 3-buten-1-one derivatives in a regioselective manner. Mechanistic studies indicate that the 1,4-aryl migration proceeds through a radical pathway.

源语言	英语
页（从-至）	7629-7633
页数	5
期刊	Angewandte Chemie - International Edition
卷	53
期	29
DOI	https://doi.org/10.1002/anie.201403383
出版状态	已出版 - 14 7月 2014
已对外发布	是

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title = "Copper-catalyzed one-pot trifluoromethylation/aryl migration/carbonyl formation with homopropargylic alcohols",

abstract = "A novel copper-catalyzed one-pot functionalization of homopropargylic alcohols that involves trifluoromethylation, aryl migration, and formation of a carbonyl moiety has been developed. This reaction constitutes the first direct conversion of homopropargylic alcohols into CF3-containing 3-butenal or 3-buten-1-one derivatives in a regioselective manner. Mechanistic studies indicate that the 1,4-aryl migration proceeds through a radical pathway.",

keywords = "Togni's reagent, aryl migration, copper, radical reactions, trifluoromethylation",

author = "Pin Gao and Shen, \{Yong Wen\} and Ran Fang and Hao, \{Xin Hua\} and Qiu, \{Zi Hang\} and Fan Yang and Yan, \{Xiao Biao\} and Qiang Wang and Gong, \{Xiang Jun\} and Liu, \{Xue Yuan\} and Liang, \{Yong Min\}",

year = "2014",

month = jul,

day = "14",

doi = "10.1002/anie.201403383",

language = "英语",

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TY - JOUR

T1 - Copper-catalyzed one-pot trifluoromethylation/aryl migration/carbonyl formation with homopropargylic alcohols

AU - Gao, Pin

AU - Shen, Yong Wen

AU - Fang, Ran

AU - Hao, Xin Hua

AU - Qiu, Zi Hang

AU - Yang, Fan

AU - Yan, Xiao Biao

AU - Wang, Qiang

AU - Gong, Xiang Jun

AU - Liu, Xue Yuan

AU - Liang, Yong Min

PY - 2014/7/14

Y1 - 2014/7/14

N2 - A novel copper-catalyzed one-pot functionalization of homopropargylic alcohols that involves trifluoromethylation, aryl migration, and formation of a carbonyl moiety has been developed. This reaction constitutes the first direct conversion of homopropargylic alcohols into CF3-containing 3-butenal or 3-buten-1-one derivatives in a regioselective manner. Mechanistic studies indicate that the 1,4-aryl migration proceeds through a radical pathway.

AB - A novel copper-catalyzed one-pot functionalization of homopropargylic alcohols that involves trifluoromethylation, aryl migration, and formation of a carbonyl moiety has been developed. This reaction constitutes the first direct conversion of homopropargylic alcohols into CF3-containing 3-butenal or 3-buten-1-one derivatives in a regioselective manner. Mechanistic studies indicate that the 1,4-aryl migration proceeds through a radical pathway.

KW - Togni's reagent

KW - aryl migration

KW - copper

KW - radical reactions

KW - trifluoromethylation

UR - https://www.scopus.com/pages/publications/84904467583

U2 - 10.1002/anie.201403383

DO - 10.1002/anie.201403383

M3 - 文章

C2 - 24938432

AN - SCOPUS:84904467583

SN - 1433-7851

VL - 53

SP - 7629

EP - 7633

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 29

ER -

Copper-catalyzed one-pot trifluoromethylation/aryl migration/carbonyl formation with homopropargylic alcohols

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