Litcius/Paper detail

Cobalt‐Catalyzed One‐Pot Asymmetric Difunctionalization of Alkynes to Access Chiral <i>gem</i>‐(Borylsilyl)alkanes

Yang’en You, Shaozhong Ge

2021Angewandte Chemie International Edition65 citationsDOI

Abstract

Abstract Enantioselective cobalt‐catalyzed one‐pot hydrosilylation and hydroboration of terminal alkynes has been developed employing a cobalt catalyst generated from Co(acac) 2 and ( R , R )‐Me‐Ferrocelane. A variety of terminal alkynes undergo this asymmetric transformation, affording the corresponding gem ‐(borylsilyl)alkane products with high enantioselectivity (up to 98 % ee ). This one‐pot reaction combines ( E )‐selective hydrosilylation of alkynes and consecutive enantioselective hydroboration of ( E )‐vinylsilanes with one chiral cobalt catalyst. This protocol represents the most straightforward approach to access versatile chiral gem ‐(borylsilyl)alkanes from readily available alkynes with commercially available cobalt salt and chiral ligand.

Topics & Concepts

HydrosilylationCobaltHydroborationCatalysisEnantioselective synthesisChemistryCombinatorial chemistryOrganic chemistryAlkyneOrganoboron and organosilicon chemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions