Stereoselective synthesis of 3-alkylideneoxindoles by palladium-catalyzed cyclization reaction of 2-(alkynyl)aryl isocyanates with organoboron reagents

Tomoya Miura; Takeharu Toyoshima; Yusuke Takahashi; Masahiro Murakami

doi:10.1021/ol801844w

Stereoselective synthesis of 3-alkylideneoxindoles by palladium-catalyzed cyclization reaction of 2-(alkynyl)aryl isocyanates with organoboron reagents

Tomoya Miura, Takeharu Toyoshima, Yusuke Takahashi, Masahiro Murakami

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

45 Citations (Scopus)

Abstract

(Chemical Equation Presented) A palladium(0)/monophosphine catalyst promotes a cyclization reaction of 2-(alkynyl)aryl isocyanates with organoboron reagents to produce stereodefined 3-alkylideneoxindoles. The alkynyl and isocyanato groups undergo oxidative cyclization with Pd(O) to form an oxapalladacycle intermediate. Subsequent transmetalation and reductive elimination afford the product.

Original language	English
Pages (from-to)	4887-4889
Number of pages	3
Journal	Organic Letters
Volume	10
Issue number	21
DOIs	https://doi.org/10.1021/ol801844w
Publication status	Published - 2008
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol801844w

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abstract = "(Chemical Equation Presented) A palladium(0)/monophosphine catalyst promotes a cyclization reaction of 2-(alkynyl)aryl isocyanates with organoboron reagents to produce stereodefined 3-alkylideneoxindoles. The alkynyl and isocyanato groups undergo oxidative cyclization with Pd(O) to form an oxapalladacycle intermediate. Subsequent transmetalation and reductive elimination afford the product.",

author = "Tomoya Miura and Takeharu Toyoshima and Yusuke Takahashi and Masahiro Murakami",

year = "2008",

doi = "10.1021/ol801844w",

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volume = "10",

pages = "4887--4889",

journal = "Organic Letters",

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T1 - Stereoselective synthesis of 3-alkylideneoxindoles by palladium-catalyzed cyclization reaction of 2-(alkynyl)aryl isocyanates with organoboron reagents

AU - Miura, Tomoya

AU - Toyoshima, Takeharu

AU - Takahashi, Yusuke

AU - Murakami, Masahiro

PY - 2008

Y1 - 2008

N2 - (Chemical Equation Presented) A palladium(0)/monophosphine catalyst promotes a cyclization reaction of 2-(alkynyl)aryl isocyanates with organoboron reagents to produce stereodefined 3-alkylideneoxindoles. The alkynyl and isocyanato groups undergo oxidative cyclization with Pd(O) to form an oxapalladacycle intermediate. Subsequent transmetalation and reductive elimination afford the product.

AB - (Chemical Equation Presented) A palladium(0)/monophosphine catalyst promotes a cyclization reaction of 2-(alkynyl)aryl isocyanates with organoboron reagents to produce stereodefined 3-alkylideneoxindoles. The alkynyl and isocyanato groups undergo oxidative cyclization with Pd(O) to form an oxapalladacycle intermediate. Subsequent transmetalation and reductive elimination afford the product.

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ER -

Stereoselective synthesis of 3-alkylideneoxindoles by palladium-catalyzed cyclization reaction of 2-(alkynyl)aryl isocyanates with organoboron reagents

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