Nickel-catalyzed synthesis of 1,3,5-trisubstituted hydantoins from acrylates and isocyanates

Tomoya Miura; Yusuke Mikano; Masahiro Murakami

doi:10.1021/ol200957y

Nickel-catalyzed synthesis of 1,3,5-trisubstituted hydantoins from acrylates and isocyanates

Tomoya Miura, Yusuke Mikano, Masahiro Murakami

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

28 Citations (Scopus)

Abstract

One molecule of acrylate reacts with two molecules of isocyanate in the presence of a nickel(0)/SIPr catalyst to give a 1,3,5-trisubstituted hydantoin. Two processes operate in sequence, the first, regioselective formation of N-substituted fumaramate from acrylate and isocyanate and, the second, ring closure of the fumaramate with incorporation of another molecule of isocyanate.

Original language	English
Pages (from-to)	3560-3563
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	14
DOIs	https://doi.org/10.1021/ol200957y
Publication status	Published - Jul 15 2011
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "One molecule of acrylate reacts with two molecules of isocyanate in the presence of a nickel(0)/SIPr catalyst to give a 1,3,5-trisubstituted hydantoin. Two processes operate in sequence, the first, regioselective formation of N-substituted fumaramate from acrylate and isocyanate and, the second, ring closure of the fumaramate with incorporation of another molecule of isocyanate.",

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AU - Miura, Tomoya

AU - Mikano, Yusuke

AU - Murakami, Masahiro

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Y1 - 2011/7/15

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AB - One molecule of acrylate reacts with two molecules of isocyanate in the presence of a nickel(0)/SIPr catalyst to give a 1,3,5-trisubstituted hydantoin. Two processes operate in sequence, the first, regioselective formation of N-substituted fumaramate from acrylate and isocyanate and, the second, ring closure of the fumaramate with incorporation of another molecule of isocyanate.

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Nickel-catalyzed synthesis of 1,3,5-trisubstituted hydantoins from acrylates and isocyanates

Abstract

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