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

Kang Wang; Jianbo Wang

doi:10.1055/s-0037-1611020

Synlett, Table of Contents

Synlett 2019; 30(05): 542-551
DOI: 10.1055/s-0037-1611020

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

Kang Wang

^aBeijing 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

^bResearch Institute of Aerospace Special Materials and Processing Technology, Beijing 100074, P. R. of China

,

Jianbo Wang *

^aBeijing 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

^cThe 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

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Abstract

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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

Key words

cross-coupling - catalysis - carbene migratory insertion - metal carbene - C–C bond formation

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References

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