Insight into the MOtBu (M = Na, K)-mediated dehydrogenation of dimethylamine-borane and transfer hydrogenation of nitriles to primary amines

Chemistry. 2024 Apr 11:e202400942. doi: 10.1002/chem.202400942. Online ahead of print.ABSTRACTSelective synthesis of primary amines from nitriles is challenging in synthetic chemistry due to the possible en-route generation of various amines and imines. Herein, we report a practical and operationally simple MOtBu-mediated (M = Na, K) transfer hydrogenation of nitriles to the corresponding primary amines with a relatively unexplored sacrificial hydrogen source (dimethylamine borane). The strategy encompasses a broad substrate scope under transition metal-free conditions and does not require any solvent. The mechanistic investigation was performed with the aid of control experiments and spectroscopic studies. The GC analysis of the reaction mixture exhibited the evolution of the H2 gas. Additionally, detailed computational calculations were undertaken to shed light on the possible intermediates and transition states involved during the present protocol.PMID:38605476 | DOI:10.1002/chem.202400942

Source: Chemistry - April 12, 2024 Category: Chemistry Authors: Deep Chowdhury Rahul Sutradhar Ankan Paul Arup Mukherjee Source Type: research