Nickel-catalyzed [2 + 2 + 2] cycloaddition reaction of isocyanates with 1,3-dienes

Masao Morimoto; Yui Nishida; Tomoya Miura; Masahiro Murakami

doi:10.1246/cl.130082

Nickel-catalyzed [2 + 2 + 2] cycloaddition reaction of isocyanates with 1,3-dienes

Masao Morimoto, Yui Nishida, Tomoya Miura, Masahiro Murakami

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

13 Citations (Scopus)

Abstract

Two molecules of an isocyanate react with one molecule of a 1,3-diene in the presence of a nickel(0) catalyst to give a 6-substituted dihydropyrimidine-2,4-dione. A five-membered azanickelacyclic intermediate is initially generated through oxidative cyclization of a hetero-pair of the isocyanate and the 1,3-diene onto nickel(0). Another molecule of the isocyanate is subsequently incorporated therein and reductive elimination follows.

Original language	English
Pages (from-to)	550-552
Number of pages	3
Journal	Chemistry Letters
Volume	42
Issue number	5
DOIs	https://doi.org/10.1246/cl.130082
Publication status	Published - 2013
Externally published	Yes

ASJC Scopus subject areas

Chemistry(all)

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abstract = "Two molecules of an isocyanate react with one molecule of a 1,3-diene in the presence of a nickel(0) catalyst to give a 6-substituted dihydropyrimidine-2,4-dione. A five-membered azanickelacyclic intermediate is initially generated through oxidative cyclization of a hetero-pair of the isocyanate and the 1,3-diene onto nickel(0). Another molecule of the isocyanate is subsequently incorporated therein and reductive elimination follows.",

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T1 - Nickel-catalyzed [2 + 2 + 2] cycloaddition reaction of isocyanates with 1,3-dienes

AU - Morimoto, Masao

AU - Nishida, Yui

AU - Miura, Tomoya

AU - Murakami, Masahiro

PY - 2013

Y1 - 2013

N2 - Two molecules of an isocyanate react with one molecule of a 1,3-diene in the presence of a nickel(0) catalyst to give a 6-substituted dihydropyrimidine-2,4-dione. A five-membered azanickelacyclic intermediate is initially generated through oxidative cyclization of a hetero-pair of the isocyanate and the 1,3-diene onto nickel(0). Another molecule of the isocyanate is subsequently incorporated therein and reductive elimination follows.

AB - Two molecules of an isocyanate react with one molecule of a 1,3-diene in the presence of a nickel(0) catalyst to give a 6-substituted dihydropyrimidine-2,4-dione. A five-membered azanickelacyclic intermediate is initially generated through oxidative cyclization of a hetero-pair of the isocyanate and the 1,3-diene onto nickel(0). Another molecule of the isocyanate is subsequently incorporated therein and reductive elimination follows.

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ER -

Nickel-catalyzed [2 + 2 + 2] cycloaddition reaction of isocyanates with 1,3-dienes

Abstract

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