Gold(I)-Catalyzed Diazo Coupling: Strategy towards Alkene Formation and Tandem Benzannulation

A gold(I)‐catalyzed cross‐coupling of diazo compounds to afford tetrasubstituted alkenes has been developed by taking advantage of a trivial electronic difference between two diazo substrates. A N‐heterocyclic‐carbene‐derived gold complex is the most effective catalyst for this transformation. Based...

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Bibliographic Details
Published in:	Angewandte Chemie International Edition Vol. 53; no. 41; pp. 11070 - 11074
Main Authors:	Zhang, Daming, Xu, Guangyang, Ding, Dong, Zhu, Chenghao, Li, Jian, Sun, Jiangtao
Format:	Journal Article
Language:	English
Published:	Weinheim WILEY-VCH Verlag 06-10-2014 WILEY‐VCH Verlag Wiley Subscription Services, Inc
Edition:	International ed. in English
Subjects:	Alkenes annulations Catalysts cross-coupling diazo compounds Electronics Formations Gold Joining Olefins Strategy Transformations gold cross-coupling annulations alkenes diazo compounds
Online Access:	Get full text
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Summary:	A gold(I)‐catalyzed cross‐coupling of diazo compounds to afford tetrasubstituted alkenes has been developed by taking advantage of a trivial electronic difference between two diazo substrates. A N‐heterocyclic‐carbene‐derived gold complex is the most effective catalyst for this transformation. Based on this new strategy, a gold(I)‐initiated benzannulation has been achieved through a tandem reaction involving a diazo cross‐coupling, 6π electrocyclization, and oxidative aromatization. Crossing paths: A gold(I)‐catalyzed cross‐coupling of diazo compounds to afford tetrasubstituted alkenes has been developed. In addition, a gold(I)‐initiated benzannulation has been achieved in a tandem reaction involving cross‐coupling of the vinyldiazoacetates, sequential 6π electrocyclization, and oxidative aromatization.
Bibliography:	ark:/67375/WNG-KV9BRFNK-P Priority Academic Program Development of Jiangsu Higher Education Institution (PAPD) This project is supported by NSFC (No. 21172023), A Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institution (PAPD) and Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology (BM2012110). istex:FD1553BB5FC201B4526F5E9E20BE118E0F3BADB6 NSFC - No. 21172023 ArticleID:ANIE201406712 Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology - No. BM2012110 These authors contributed equally to this work. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201406712