Unravelling the underlying mechanism of the reduction of aldehydes/ketones with metal borohydride in an aprotic solvent

Chem Commun (Camb). 2024 Apr 3. doi: 10.1039/d3cc06108f. Online ahead of print.ABSTRACTThe reduction mechanism of aldehyde/ketones with M(BH4)n is not fully understood, even though the hydroboration mechanism of weak Lewis base borane complexes is known to involve a four-membered ring transition state. Herein, the reduction mechanism of M(BH4)n in aprotic solvents has been elucidated for a six-membered ring, in which hydride transfer to the C atom from the B atom, formation of an L·BH3 adduct, and disproportionation of (BH3(OR)-) borane are involved. The metal cations and solvents participate in and significantly influence the reaction procedure. We believe that this mechanistic study would provide a further reference for the application of M(BH4)n in organic reactions.PMID:38568798 | DOI:10.1039/d3cc06108f

Source: Chemical Communications - April 3, 2024 Category: Chemistry Authors: Xinying Li Jia-Xin Kang Shasha Liang Xi-Hong Long Yan-Na Ma Xuenian Chen Source Type: research