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

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

212 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
Externally published	Yes

Keywords

catalysis
gold
indole
nitrenes
umpolung

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10.1002/anie.201103014

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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.",

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

year = "2011",

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day = "29",

doi = "10.1002/anie.201103014",

language = "English (US)",

volume = "50",

pages = "8358--8362",

journal = "Angewandte Chemie - International Edition",

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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

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DO - 10.1002/anie.201103014

M3 - Article

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VL - 50

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 36

ER -

Umpolung reactivity of indole through gold catalysis

Abstract

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