Rh/Cu-Catalyzed Cascade [4+2] Vinylic C−H O-Annulation and Ring Contraction of α-Aryl Enones with Alkynes in Air

Yinsong Zhao; Shiqing Li; Xuesong Zheng; Junbin Tang; Zhijie She; Ge Gao; Jingsong You

doi:10.1002/anie.201612147

Rh/Cu-Catalyzed Cascade [4+2] Vinylic C−H O-Annulation and Ring Contraction of α-Aryl Enones with Alkynes in Air

Yinsong Zhao
, Shiqing Li
, Xuesong Zheng
, Junbin Tang
, Zhijie She
, Ge Gao^*
, Jingsong You

^*Corresponding author for this work

Sichuan University

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

74 Scopus citations

Abstract

An unprecedented Rh-catalyzed ketone-directed vinylic C−H activation/[4+2] O-annulation of α-aryl enones with internal alkynes followed by a Cu-catalyzed ring contraction in air to provide multiaryl-substituted furan derivatives has been developed. The preliminary mechanism study identifies the active pyrylium salt as the key intermediate.

Original language	English
Pages (from-to)	4286-4289
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	15
DOIs	https://doi.org/10.1002/anie.201612147
State	Published - 3 Apr 2017
Externally published	Yes

Keywords

O-annulation
furans
pyrylium
vinylic C−H activation
α-aryl enone

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10.1002/anie.201612147

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title = "Rh/Cu-Catalyzed Cascade [4+2] Vinylic C−H O-Annulation and Ring Contraction of α-Aryl Enones with Alkynes in Air",

abstract = "An unprecedented Rh-catalyzed ketone-directed vinylic C−H activation/[4+2] O-annulation of α-aryl enones with internal alkynes followed by a Cu-catalyzed ring contraction in air to provide multiaryl-substituted furan derivatives has been developed. The preliminary mechanism study identifies the active pyrylium salt as the key intermediate.",

keywords = "O-annulation, furans, pyrylium, vinylic C−H activation, α-aryl enone",

author = "Yinsong Zhao and Shiqing Li and Xuesong Zheng and Junbin Tang and Zhijie She and Ge Gao and Jingsong You",

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

year = "2017",

month = apr,

day = "3",

doi = "10.1002/anie.201612147",

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T1 - Rh/Cu-Catalyzed Cascade [4+2] Vinylic C−H O-Annulation and Ring Contraction of α-Aryl Enones with Alkynes in Air

AU - Zhao, Yinsong

AU - Li, Shiqing

AU - Zheng, Xuesong

AU - Tang, Junbin

AU - She, Zhijie

AU - Gao, Ge

AU - You, Jingsong

PY - 2017/4/3

Y1 - 2017/4/3

N2 - An unprecedented Rh-catalyzed ketone-directed vinylic C−H activation/[4+2] O-annulation of α-aryl enones with internal alkynes followed by a Cu-catalyzed ring contraction in air to provide multiaryl-substituted furan derivatives has been developed. The preliminary mechanism study identifies the active pyrylium salt as the key intermediate.

AB - An unprecedented Rh-catalyzed ketone-directed vinylic C−H activation/[4+2] O-annulation of α-aryl enones with internal alkynes followed by a Cu-catalyzed ring contraction in air to provide multiaryl-substituted furan derivatives has been developed. The preliminary mechanism study identifies the active pyrylium salt as the key intermediate.

KW - O-annulation

KW - furans

KW - pyrylium

KW - vinylic C−H activation

KW - α-aryl enone

UR - https://www.scopus.com/pages/publications/85014780999

U2 - 10.1002/anie.201612147

DO - 10.1002/anie.201612147

M3 - 文章

C2 - 28276622

AN - SCOPUS:85014780999

SN - 1433-7851

VL - 56

SP - 4286

EP - 4289

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 15

ER -

Rh/Cu-Catalyzed Cascade [4+2] Vinylic C−H O-Annulation and Ring Contraction of α-Aryl Enones with Alkynes in Air

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Keywords

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