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

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.

Automated summary

AgSbF6 has been established as an effective catalyst for the hydroboration of diverse isocyanates, yielding selective N-boryl formamides or N-boryl methylamines under different conditions. Additionally, this catalyst system selectively hydroborates various N-heterocycles, with pyridine derivatives preferentially undergoing 1,4 hydroboration and quinolines observed to undergo complete heterocycle hydrogenation to form tetrahydroquinoline (after hydrolysis).