Silver-Free Palladium-Catalyzed sp(3) and sp(2) C-H Alkynylation Promoted by a 1,2,3-Triazole Amine Directing Group

Org Lett. 2016 Jun 17;18(12):2970-3. doi: 10.1021/acs.orglett.6b01319. Epub 2016 Jun 6.

Abstract

Triazole amine was identified as an effective directing group in promoting C-H alkynylation under silver-free conditions. No other external oxidant was required, and the alkynylation products were received in good to excellent yields. X-ray crystallographic analysis confirmed a direct C-H activation intermediate. Other typical directing groups, including pyridine amine (PIP) and 8-aminoquinoline (QA), gave almost no reaction under identical conditions, which highlighted the unique reactivity of the triazole directing group in direct C-H functionalization.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.