Azaindole synthesis through dual activation catalysis with N-heterocyclic carbenes

Hayden A. Sharma; M. Todd Hovey; Karl A. Scheidt

doi:10.1039/c6cc04735a

Azaindole synthesis through dual activation catalysis with N-heterocyclic carbenes

Hayden A. Sharma, M. Todd Hovey, Karl A. Scheidt^*

^*Corresponding author for this work

Chemistry

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

15 Scopus citations

Abstract

A convergent, transition-metal-free synthesis of 2-aryl-azaindoles has been developed. The interception of a reactive aza-ortho-azaquinone methide intermediate by an acyl anion equivalent generated through carbene catalysis provides high yields, a wide substrate scope, and the synthesis of previously inaccessible azaindoles.

Original language	English (US)
Pages (from-to)	9283-9286
Number of pages	4
Journal	Chemical Communications
Volume	52
Issue number	59
DOIs	https://doi.org/10.1039/c6cc04735a
State	Published - 2016

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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title = "Azaindole synthesis through dual activation catalysis with N-heterocyclic carbenes",

abstract = "A convergent, transition-metal-free synthesis of 2-aryl-azaindoles has been developed. The interception of a reactive aza-ortho-azaquinone methide intermediate by an acyl anion equivalent generated through carbene catalysis provides high yields, a wide substrate scope, and the synthesis of previously inaccessible azaindoles.",

author = "Sharma, {Hayden A.} and {Todd Hovey}, M. and Scheidt, {Karl A.}",

note = "Funding Information: HAS, MTH, and KAS acknowledge financial support generously provided by the NIH (NIGMS R01-GM073072). HAS thanks Northwestern University for a Summer Undergraduate Research Grant. Publisher Copyright: {\textcopyright} 2016 The Royal Society of Chemistry.",

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doi = "10.1039/c6cc04735a",

language = "English (US)",

volume = "52",

pages = "9283--9286",

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T1 - Azaindole synthesis through dual activation catalysis with N-heterocyclic carbenes

AU - Sharma, Hayden A.

AU - Todd Hovey, M.

AU - Scheidt, Karl A.

N1 - Funding Information: HAS, MTH, and KAS acknowledge financial support generously provided by the NIH (NIGMS R01-GM073072). HAS thanks Northwestern University for a Summer Undergraduate Research Grant. Publisher Copyright: © 2016 The Royal Society of Chemistry.

PY - 2016

Y1 - 2016

N2 - A convergent, transition-metal-free synthesis of 2-aryl-azaindoles has been developed. The interception of a reactive aza-ortho-azaquinone methide intermediate by an acyl anion equivalent generated through carbene catalysis provides high yields, a wide substrate scope, and the synthesis of previously inaccessible azaindoles.

AB - A convergent, transition-metal-free synthesis of 2-aryl-azaindoles has been developed. The interception of a reactive aza-ortho-azaquinone methide intermediate by an acyl anion equivalent generated through carbene catalysis provides high yields, a wide substrate scope, and the synthesis of previously inaccessible azaindoles.

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U2 - 10.1039/c6cc04735a

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JO - Chemical Communications

JF - Chemical Communications

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ER -

Azaindole synthesis through dual activation catalysis with N-heterocyclic carbenes

Abstract

ASJC Scopus subject areas

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