Highly Stereoselective Gold-Catalyzed Coupling of Diazo Reagents and Fluorinated Enol Silyl Ethers to Tetrasubstituted Alkenes

Fu Min Liao; Zhong Yan Cao; Jin Sheng Yu; Jian Zhou

doi:10.1002/anie.201611625

Highly Stereoselective Gold-Catalyzed Coupling of Diazo Reagents and Fluorinated Enol Silyl Ethers to Tetrasubstituted Alkenes

Fu Min Liao
, Zhong Yan Cao
, Jin Sheng Yu
, Jian Zhou^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

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

101 Scopus citations

Abstract

We report a highly stereoselective synthesis of all-carbon or fluorinated tetrasubstituted alkenes from diazo reagents and fluorinated enol silyl ethers, using C−F bond as a synthetic handle. Cationic Au^Icatalysis plays a key role in this reaction. Remarkable fluorine effects on the reactivity and selectivity was also observed.

Original language	English
Pages (from-to)	2459-2463
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	9
DOIs	https://doi.org/10.1002/anie.201611625
State	Published - 20 Feb 2017

Keywords

coupling reactions
diazo reagents
fluorine effects
gold catalysis
olefination

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10.1002/anie.201611625

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title = "Highly Stereoselective Gold-Catalyzed Coupling of Diazo Reagents and Fluorinated Enol Silyl Ethers to Tetrasubstituted Alkenes",

abstract = "We report a highly stereoselective synthesis of all-carbon or fluorinated tetrasubstituted alkenes from diazo reagents and fluorinated enol silyl ethers, using C−F bond as a synthetic handle. Cationic AuIcatalysis plays a key role in this reaction. Remarkable fluorine effects on the reactivity and selectivity was also observed.",

keywords = "coupling reactions, diazo reagents, fluorine effects, gold catalysis, olefination",

author = "Liao, \{Fu Min\} and Cao, \{Zhong Yan\} and Yu, \{Jin Sheng\} and Jian Zhou",

note = "Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

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T1 - Highly Stereoselective Gold-Catalyzed Coupling of Diazo Reagents and Fluorinated Enol Silyl Ethers to Tetrasubstituted Alkenes

AU - Liao, Fu Min

AU - Cao, Zhong Yan

AU - Yu, Jin Sheng

AU - Zhou, Jian

PY - 2017/2/20

Y1 - 2017/2/20

N2 - We report a highly stereoselective synthesis of all-carbon or fluorinated tetrasubstituted alkenes from diazo reagents and fluorinated enol silyl ethers, using C−F bond as a synthetic handle. Cationic AuIcatalysis plays a key role in this reaction. Remarkable fluorine effects on the reactivity and selectivity was also observed.

AB - We report a highly stereoselective synthesis of all-carbon or fluorinated tetrasubstituted alkenes from diazo reagents and fluorinated enol silyl ethers, using C−F bond as a synthetic handle. Cationic AuIcatalysis plays a key role in this reaction. Remarkable fluorine effects on the reactivity and selectivity was also observed.

KW - coupling reactions

KW - diazo reagents

KW - fluorine effects

KW - gold catalysis

KW - olefination

UR - https://www.scopus.com/pages/publications/85009787135

U2 - 10.1002/anie.201611625

DO - 10.1002/anie.201611625

M3 - 文章

C2 - 28097773

AN - SCOPUS:85009787135

SN - 1433-7851

VL - 56

SP - 2459

EP - 2463

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 9

ER -

Highly Stereoselective Gold-Catalyzed Coupling of Diazo Reagents and Fluorinated Enol Silyl Ethers to Tetrasubstituted Alkenes

Abstract

Keywords

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