C[double bond, length as m-dash]N bond formation via palladium-catalyzed carbene insertion into N[double bond, length as m-dash]N bonds: inhibiting the general 1,2-migration process of ylide intermediates

A new example of C[double bond, length as m-dash]N double bond formation in metal carbene insertion reactions is reported. Remarkably, the general 1,2-migration process of the corresponding ylide intermediates in X-H carbene insertion reactions that leads to C-X single bond formation is completely i...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2017-02, Vol.53 (18), p.2697-2700
Main Authors: Zhu, Chuanle, Chen, Pengquan, Zhu, Rui, Lin, Zhiming, Wu, Wanqing, Jiang, Huanfeng
Format: Article
Language:English
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Summary:A new example of C[double bond, length as m-dash]N double bond formation in metal carbene insertion reactions is reported. Remarkably, the general 1,2-migration process of the corresponding ylide intermediates in X-H carbene insertion reactions that leads to C-X single bond formation is completely inhibited by replacing the H atom with a nitrogen atom. This palladium-catalyzed carbene insertion reaction with N[double bond, length as m-dash]N double bonds gave various N,N-disubstituted hydrazone products in high yields.
ISSN:1359-7345
1364-548X
DOI:10.1039/c6cc10187a