Synthesis of DBpin using Earth-abundant metal catalysis

Cummins, Andrew W.M. and Li, Shuyang and Willcox, Dominic R. and Muilu, Tommi and Docherty, Jamie H. and Thomas, Stephen P. (2020) Synthesis of DBpin using Earth-abundant metal catalysis. Tetrahedron, 76 (15): 131084. ISSN 0040-4020

Abstract

The synthesis of DBpin was achieved using (EtBIP)CoCl2 or (tBuPNN)FeCl2 as pre-catalysts activated with NaOtBu. (EtBIP)CoCl2 was used as a pre-catalyst for the hydrogen isotope exchange of HBpin with D2, and (tBuPNN)FeCl2 for deuterogenolysis of B2pin2. The one-pot, tandem hydrogenolysis-hydroboration/deuterogenolysis-deuteroboration reaction of terminal alkenes could be catalysed by (tBuPNN)FeCl2 to give alkyl boronic esters.