Synthesis of 3,3-disubstituted oxindoles by palladium-catalyzed tandem reaction of 2-(alkynyl)aryl isocyanates with benzylic alcohols

Takeharu Toyoshima; Yusuke Mikano; Tomoya Miura; Masahiro Murakami

doi:10.1021/ol101892b

Synthesis of 3,3-disubstituted oxindoles by palladium-catalyzed tandem reaction of 2-(alkynyl)aryl isocyanates with benzylic alcohols

Takeharu Toyoshima, Yusuke Mikano, Tomoya Miura, Masahiro Murakami

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

20 Citations (Scopus)

Abstract

A palladium complex sequentially promoted two mechanistically distinct reactions, the first, cyclization of 2-(alkynyl)aryl isocyanates with benzylic alcohols, and the second, [1,3] rearrangement of a benzyl group from oxygen to carbon, furnishing 3,3-disubstituted oxindoles in one pot.

Original language	English
Pages (from-to)	4584-4587
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	20
DOIs	https://doi.org/10.1021/ol101892b
Publication status	Published - Oct 15 2010
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol101892b

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title = "Synthesis of 3,3-disubstituted oxindoles by palladium-catalyzed tandem reaction of 2-(alkynyl)aryl isocyanates with benzylic alcohols",

abstract = "A palladium complex sequentially promoted two mechanistically distinct reactions, the first, cyclization of 2-(alkynyl)aryl isocyanates with benzylic alcohols, and the second, [1,3] rearrangement of a benzyl group from oxygen to carbon, furnishing 3,3-disubstituted oxindoles in one pot.",

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

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doi = "10.1021/ol101892b",

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T1 - Synthesis of 3,3-disubstituted oxindoles by palladium-catalyzed tandem reaction of 2-(alkynyl)aryl isocyanates with benzylic alcohols

AU - Toyoshima, Takeharu

AU - Mikano, Yusuke

AU - Miura, Tomoya

AU - Murakami, Masahiro

PY - 2010/10/15

Y1 - 2010/10/15

N2 - A palladium complex sequentially promoted two mechanistically distinct reactions, the first, cyclization of 2-(alkynyl)aryl isocyanates with benzylic alcohols, and the second, [1,3] rearrangement of a benzyl group from oxygen to carbon, furnishing 3,3-disubstituted oxindoles in one pot.

AB - A palladium complex sequentially promoted two mechanistically distinct reactions, the first, cyclization of 2-(alkynyl)aryl isocyanates with benzylic alcohols, and the second, [1,3] rearrangement of a benzyl group from oxygen to carbon, furnishing 3,3-disubstituted oxindoles in one pot.

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Synthesis of 3,3-disubstituted oxindoles by palladium-catalyzed tandem reaction of 2-(alkynyl)aryl isocyanates with benzylic alcohols

Abstract

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