Ru(II)-Catalyzed Cross-Coupling of Cyclopropenes with Diazo Compounds: Formation of Olefins from Two Different Carbene Precursors

Bo Wang; Heng Yi; Hang Zhang; Tong Sun; Yan Zhang; Jianbo Wang

doi:10.1021/acs.joc.7b02634

Ru(II)-Catalyzed Cross-Coupling of Cyclopropenes with Diazo Compounds: Formation of Olefins from Two Different Carbene Precursors

J Org Chem. 2018 Jan 19;83(2):1026-1032. doi: 10.1021/acs.joc.7b02634. Epub 2018 Jan 4.

Authors

Bo Wang¹, Heng Yi¹, Hang Zhang¹, Tong Sun¹, Yan Zhang¹, Jianbo Wang^{1

2}

Affiliations

¹ Beijing National Laboratory of Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University , Beijing 100871, China.
² The State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences , Shanghai 200032, China.

PMID: 29251509
DOI: 10.1021/acs.joc.7b02634

Abstract

Formal carbene dimerization is a convergent method for the synthesis of alkenes. Herein, we report a Ru(II)-catalyzed carbene dimerization of cyclopropenes and diazo compounds. The yields are up to 97% and the stereoselectivity are up to >20:1. Mechanistically, it has been experimentally demonstrated that the catalyst reacts with cyclopropene first to generate a Ru(II)-carbene species, which is attacked by nucleophilic diazo substrate, followed by dinitrogen extrusion to form the double bond.