Cyanamide synthesis by the palladium-catalyzed cleavage of a Si-N bond

Shin Kamijo; Tienan Jin; Yoshinori Yamamoto

doi:10.1002/1521-3773(20020517)41:10<1780::aid-anie1780>3.0.co;2-%23

Cyanamide synthesis by the palladium-catalyzed cleavage of a Si-N bond

Shin Kamijo, Tienan Jin, Yoshinori Yamamoto

SCI - Research and Analytical Center for Giant Molecules

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

37 Citations (Scopus)

Abstract

A palladium mimic of the Curtius rearrangement and a palladium-catalyzed geminal addition of a Si-N bond occurs in the high-yielding synthesis of cyanamides from isocyanides and trimethylsilyl azide in the presence of a palladium catalyst (see scheme). A wide range of functional groups are tolerated in the reaction.

Original language	English
Pages (from-to)	1780-1782
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	41
Issue number	10
DOIs	https://doi.org/10.1002/1521-3773(20020517)41:10<1780::aid-anie1780>3.0.co;2-%23
Publication status	Published - 2002 Jan 1

Keywords

Amides
Azomethine ylides
Cycloaddition
Natural products
Synthetic methods

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/1521-3773(20020517)41:10<1780::aid-anie1780>3.0.co;2-%23

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AU - Yamamoto, Yoshinori

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N2 - A palladium mimic of the Curtius rearrangement and a palladium-catalyzed geminal addition of a Si-N bond occurs in the high-yielding synthesis of cyanamides from isocyanides and trimethylsilyl azide in the presence of a palladium catalyst (see scheme). A wide range of functional groups are tolerated in the reaction.

AB - A palladium mimic of the Curtius rearrangement and a palladium-catalyzed geminal addition of a Si-N bond occurs in the high-yielding synthesis of cyanamides from isocyanides and trimethylsilyl azide in the presence of a palladium catalyst (see scheme). A wide range of functional groups are tolerated in the reaction.

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KW - Cycloaddition

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KW - Synthetic methods

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