Silver-Catalyzed Vinylcarbene Insertion into C-C Bonds of 1,3-Diketones with Vinyl- N-triftosylhydrazones

Yong Wu; Yongquan Ning; Xinyue Han; Peiqiu Liao; Ying Xia; Paramasivam Sivaguru; Xihe Bi

doi:10.1021/acs.orglett.2c03176

Silver-Catalyzed Vinylcarbene Insertion into C-C Bonds of 1,3-Diketones with Vinyl- N-triftosylhydrazones

Org Lett. 2022 Nov 11;24(44):8136-8141. doi: 10.1021/acs.orglett.2c03176. Epub 2022 Oct 31.

Authors

Yong Wu¹, Yongquan Ning¹, Xinyue Han¹, Peiqiu Liao¹, Ying Xia¹, Paramasivam Sivaguru¹, Xihe Bi^{1

2}

Affiliations

¹ Jilin Province Key Laboratory of Organic Functional Molecular Design and Synthesis, Department of Chemistry, Northeast Normal University, Changchun, Jilin 130024, China.
² State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China.

PMID: 36314934
DOI: 10.1021/acs.orglett.2c03176

Abstract

We describe the silver-catalyzed formal insertion of a vinylcarbene into unstrained C(CO)-C bonds of 1,3-diketones using vinyl-N-triftosylhydrazones as vinylcarbene precursors. This method allows the rapid synthesis of otherwise inaccessible 2-vinyl-substituted 1,4-diketones from relatively simple substrates. This mild catalytic protocol exhibits a good functional group tolerance and substrate scope and allows for good chemoselectivity control. The preliminary theoretical calculations suggest that the reaction proceeds through a stepwise enol cyclopropanation/retro-aldol pathway.