Combining gold(I)/gold(III) catalysis and C-H functionalization: A formal intramolecular [3+2] annulation towards tricyclic indolines and mechanistic studies

Guozhu Zhang; Yingdong Luo; Yanzhao Wang; Liming Zhang

doi:10.1002/anie.201100293

Combining gold(I)/gold(III) catalysis and C-H functionalization: A formal intramolecular [3+2] annulation towards tricyclic indolines and mechanistic studies

Guozhu Zhang
, Yingdong Luo
, Yanzhao Wang
, Liming Zhang

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

122 Scopus citations

Abstract

Gold rush: A combination of oxidative gold(I)/gold(III) catalysis and C-H functionalization led to the first oxidative coupling between in situ generated alkyl gold reagents and C sp 2-H bonds, affording tricyclic indolines through a formal [3+2] annulation between a vinyl group and an aniline moiety [see scheme; Tf=trifluoromethanesulfonyl, Selectfluor=1-chloromethyl-4-fluoro-1,4- diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)].

Original language	English (US)
Pages (from-to)	4450-4454
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	19
DOIs	https://doi.org/10.1002/anie.201100293
State	Published - May 2 2011
Externally published	Yes

Keywords

gold
homogeneous catalysis
nitrogen heterocycles
oxidation
reaction mechanisms

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10.1002/anie.201100293

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abstract = "Gold rush: A combination of oxidative gold(I)/gold(III) catalysis and C-H functionalization led to the first oxidative coupling between in situ generated alkyl gold reagents and C sp 2-H bonds, affording tricyclic indolines through a formal [3+2] annulation between a vinyl group and an aniline moiety [see scheme; Tf=trifluoromethanesulfonyl, Selectfluor=1-chloromethyl-4-fluoro-1,4- diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)].",

keywords = "gold, homogeneous catalysis, nitrogen heterocycles, oxidation, reaction mechanisms",

author = "Guozhu Zhang and Yingdong Luo and Yanzhao Wang and Liming Zhang",

year = "2011",

month = may,

day = "2",

doi = "10.1002/anie.201100293",

language = "English (US)",

volume = "50",

pages = "4450--4454",

journal = "Angewandte Chemie - International Edition",

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publisher = "John Wiley and Sons Ltd",

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TY - JOUR

T1 - Combining gold(I)/gold(III) catalysis and C-H functionalization

T2 - A formal intramolecular [3+2] annulation towards tricyclic indolines and mechanistic studies

AU - Zhang, Guozhu

AU - Luo, Yingdong

AU - Wang, Yanzhao

AU - Zhang, Liming

PY - 2011/5/2

Y1 - 2011/5/2

N2 - Gold rush: A combination of oxidative gold(I)/gold(III) catalysis and C-H functionalization led to the first oxidative coupling between in situ generated alkyl gold reagents and C sp 2-H bonds, affording tricyclic indolines through a formal [3+2] annulation between a vinyl group and an aniline moiety [see scheme; Tf=trifluoromethanesulfonyl, Selectfluor=1-chloromethyl-4-fluoro-1,4- diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)].

AB - Gold rush: A combination of oxidative gold(I)/gold(III) catalysis and C-H functionalization led to the first oxidative coupling between in situ generated alkyl gold reagents and C sp 2-H bonds, affording tricyclic indolines through a formal [3+2] annulation between a vinyl group and an aniline moiety [see scheme; Tf=trifluoromethanesulfonyl, Selectfluor=1-chloromethyl-4-fluoro-1,4- diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)].

KW - gold

KW - homogeneous catalysis

KW - nitrogen heterocycles

KW - oxidation

KW - reaction mechanisms

UR - https://www.scopus.com/pages/publications/79955510598

UR - https://www.scopus.com/pages/publications/79955510598#tab=citedBy

U2 - 10.1002/anie.201100293

DO - 10.1002/anie.201100293

M3 - Article

C2 - 21480449

AN - SCOPUS:79955510598

SN - 1433-7851

VL - 50

SP - 4450

EP - 4454

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 19

ER -

Combining gold(I)/gold(III) catalysis and C-H functionalization: A formal intramolecular [3+2] annulation towards tricyclic indolines and mechanistic studies

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