Umpolung reactivity of indole through gold catalysis

Biao Lu; Yingdong Luo; Lianzhu Liu; Longwu Ye; Yanzhao Wang; Liming Zhang

doi:10.1002/anie.201103014

Umpolung reactivity of indole through gold catalysis

Biao Lu, Yingdong Luo, Lianzhu Liu, Longwu Ye, Yanzhao Wang, Liming Zhang

Chemistry (Twin Cities)

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

172 Scopus citations

Abstract

Electrophilic indole? Indoles, which are typically nucleophilic, can be made electrophilic through gold catalysis. By using an ortho-azido group to deliver a nitrene intramolecularly, an arylalkyne is converted into a gold carbene intermediate containing an indole skeleton that is highly electrophilic at the 3-position. A range of functionalized indoles is readily accessed by utilizing this strategy.

Original language	English (US)
Pages (from-to)	8358-8362
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	36
DOIs	https://doi.org/10.1002/anie.201103014
State	Published - Aug 29 2011

Keywords

catalysis
gold
indole
nitrenes
umpolung

Access

10.1002/anie.201103014

Fingerprint Dive into the research topics of 'Umpolung reactivity of indole through gold catalysis'. Together they form a unique fingerprint.

Cite this

@article{80a332414b494a01bff6c42135ee720e,

title = "Umpolung reactivity of indole through gold catalysis",

abstract = "Electrophilic indole? Indoles, which are typically nucleophilic, can be made electrophilic through gold catalysis. By using an ortho-azido group to deliver a nitrene intramolecularly, an arylalkyne is converted into a gold carbene intermediate containing an indole skeleton that is highly electrophilic at the 3-position. A range of functionalized indoles is readily accessed by utilizing this strategy.",

keywords = "catalysis, gold, indole, nitrenes, umpolung",

author = "Biao Lu and Yingdong Luo and Lianzhu Liu and Longwu Ye and Yanzhao Wang and Liming Zhang",

year = "2011",

month = aug,

day = "29",

doi = "10.1002/anie.201103014",

language = "English (US)",

volume = "50",

pages = "8358--8362",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "36",

}

TY - JOUR

T1 - Umpolung reactivity of indole through gold catalysis

AU - Lu, Biao

AU - Luo, Yingdong

AU - Liu, Lianzhu

AU - Ye, Longwu

AU - Wang, Yanzhao

AU - Zhang, Liming

PY - 2011/8/29

Y1 - 2011/8/29

N2 - Electrophilic indole? Indoles, which are typically nucleophilic, can be made electrophilic through gold catalysis. By using an ortho-azido group to deliver a nitrene intramolecularly, an arylalkyne is converted into a gold carbene intermediate containing an indole skeleton that is highly electrophilic at the 3-position. A range of functionalized indoles is readily accessed by utilizing this strategy.

AB - Electrophilic indole? Indoles, which are typically nucleophilic, can be made electrophilic through gold catalysis. By using an ortho-azido group to deliver a nitrene intramolecularly, an arylalkyne is converted into a gold carbene intermediate containing an indole skeleton that is highly electrophilic at the 3-position. A range of functionalized indoles is readily accessed by utilizing this strategy.

KW - catalysis

KW - gold

KW - indole

KW - nitrenes

KW - umpolung

UR - http://www.scopus.com/inward/record.url?scp=80052080476&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=80052080476&partnerID=8YFLogxK

U2 - 10.1002/anie.201103014

DO - 10.1002/anie.201103014

M3 - Article

C2 - 21761530

AN - SCOPUS:80052080476

VL - 50

SP - 8358

EP - 8362

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 36

ER -

Umpolung reactivity of indole through gold catalysis

Abstract

Keywords

Access

Other files and links

Cite this