Functionalization of remote C(sp³)-H bonds enabled by copper-catalyzed coupling of O-acyloximes with terminal alkynes.

ABSTRACT: Transition metal catalyzed Sonogashira cross-coupling of terminal alkynes with aryl(vinyl) (pseudo)halides has been successfully extended to alkyl halides for the synthesis of functionalized internal alkynes. The direct alkynylation of remote unfunctionalized sp³ carbon by terminal alkynes remains difficult to realize. We report herein an approach to this synthetic challenge by developing two catalytic remote sp³ carbon alkynylation protocols. In the presence of a catalytic amount of Cu(I) salt and a tridentate ligand (tBu₃-terpyridine), O-acyloximes derived from cycloalkanones and acyclic ketones are efficiently coupled with terminal alkynes to afford a variety of γ- and δ-alkynyl nitriles and γ-alkynyl ketones, respectively. These reactions proceed throug

SUBMITTER: Li Z 

PROVIDER: S-EPMC6972843 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature