CoIII-Catalyzed C-H Alkenylation and Allylation with Cyclopropenes via Sequential C-H/C-C Bond Activation

Ye Lim Kim, Sun A. Park, Seoung Mi Choi, Jong Un Park, Ju Hyun Kim

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

An atom-economical strategy for the C-H alkenylation and C-H allylation of arenes by employing cyclopropenes as versatile alkenylating and allylating reagents is reported, catalyzed by cobalt. The Co-catalyzed C-H alkenylation process involves sequential C-H and C-C bond cleavage. Under the optimized conditions, broad-ranging alkenylated (hetero)arenes were synthesized with complete (E)-stereoselectivity (up to 91%). The consecutive C-H allylation proved viable under basic conditions via double-bond migration of the initially generated alkenyl (hetero)arenes, thus leading to allylated (hetero)arenes with high stereoselectivity of olefin (E/Z ratio = 91:9 to 100:0).

Original languageEnglish
Pages (from-to)6674-6679
Number of pages6
JournalOrganic Letters
Volume23
Issue number17
DOIs
StatePublished - 3 Sep 2021

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