Litcius/Paper detail

Cobalt-catalyzed branched selective hydroallylation of terminal alkynes

Jieping Chen, Jiale Ying, Zhan Lu

2022Nature Communications35 citationsDOIOpen Access PDF

Abstract

Here, we reported a cobalt-hydride-catalyzed Markovnikov-type hydroallylation of terminal alkynes with allylic electrophile to access valuable and branched skipped dienes (1,4-dienes) with good regioselectivity. This operationally simple protocol exhibits excellent functional group tolerance and exceptional substrate scope. The reactions could be carried out in gram-scale with TON (turn over number) up to 1160, and the products could be easily derivatized. The preliminary mechanism of electrophilic allylation of α-selective cobalt alkenyl intermediate was proposed based on deuterium labeling experiment and kinetic studies.

Topics & Concepts

ElectrophileRegioselectivityMarkovnikov's ruleCatalysisCobaltAllylic rearrangementChemistryCombinatorial chemistrySubstrate (aquarium)HydrideFunctional groupOrganic chemistryHydrogenBiologyPolymerEcologyCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsOrganoboron and organosilicon chemistry