Synlett 2019; 30(05): 542-551
DOI: 10.1055/s-0037-1611020
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© Georg Thieme Verlag Stuttgart · New York

Transition-Metal-Catalyzed Cross-Coupling with Non-Diazo Carbene Precursors

Kang Wang
a  Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular ­Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China
b  Research Institute of Aerospace Special Materials and Processing Technology, Beijing 100074, P. R. of China
,
a  Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular ­Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, P. R. of China
c  The State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China   eMail: wangjb@pku.edu.cn
› Institutsangaben
The project has been supported by the National Basic Research ­Program of China (973 Program, No. 2015CB856600) and the Natural Science Foundation of China (21332002).
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Publikationsverlauf

Received: 16. August 2018

Accepted after revision: 17. September 2018

Publikationsdatum:
16. Oktober 2018 (eFirst)

Abstract

Transition-metal-catalyzed cross-coupling reactions through metal carbene migratory insertion have emerged as powerful methodology for carbon–carbon bond constructions. Typically, diazo compounds (or in situ generated diazo compounds from N-tosylhydrazones) have been employed as the metal carbene precursors for this type of cross-coupling reactions. Recently, cross-coupling reactions employing non-diazo carbene precursors, such as conjugated ene-yne-ketones, allenyl ketones, alkynes, cyclopropenes, and Cr(0) Fischer carbenes, have been developed. This account will summarize our efforts in the development of transition-metal-catalyzed cross-coupling reactions with these non-diazo carbene precursors.

1 Introduction

2 Cross-Coupling with Ene-yne-ketones, Allenyl Ketones, and Alkynes

3 Cross-Coupling Involving Ring-Opening of Cyclopropenes

4 Palladium-Catalyzed Cross-Coupling with Chromium(0) Fischer Carbenes

5 Conclusion

 
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