Simple silver(i)-salt catalyzed selective hydroboration of isocyanates, pyridines, and quinolines

Abstract

AgSbF₆ has been established as an effective catalyst for the hydroboration of structurally and electronically diverse isocyanates under ligand- and solvent-free conditions which selectively yielded either N-boryl formamides or N-boryl methylamines under different conditions. Further, various N-heterocycles can be selectively hydroborated using this simple catalytic system; pyridine derivatives undergo preferential 1,4 hydroboration whereas the formation of tetrahydroquinoline (after hydrolysis) via complete heterocycle hydrogenation was observed for quinolines.