Department of Chemistry, School of Sciences and Humanities, Nazarbayev University, 53 Kabanbay Batyr Avenue, Nur-Sultan, 010000, Kazakhstan.
Core Facilities, Office of the Provost, Nazarbayev University, 53 Kabanbay Batyr Avenue, Nur-Sultan, 010000, Kazakhstan.
Chemistry. 2020 Apr 16;26(22):4963-4968. doi: 10.1002/chem.202000753. Epub 2020 Mar 31.
The commercially available and bench-stable Co(acac) /dpephos system is employed as a precatalyst for selective and efficient room temperature hydroboration of organic nitriles with HBPin to produce a series of N,N-diborylamines [RN(BPin) ], which react in situ with aldehydes to give aldimines. Formation of aldimines from N,N-diborylamines does not require a dehydrating agent, is applicable to a wide range of N,N-diborylamine and aldehyde substrates and is highly chemoselective, being unaffected by various common functional groups, such as alkenes, alkynes, secondary amines, ketones, esters, amides, carboxylic acids, pyridines, nitriles, and nitro compounds. The overall transformation represents a synthetically valuable approach to aldimines from nitriles and can be performed in a sequential one-pot manner, tolerating ester, lactone, carboxamide and unactivated alkene functionalities.
市售且稳定的 Co(acac)/dpephos 体系被用作预催化剂，用于在室温下选择性和高效地对有机腈进行硼氢化，得到一系列 N,N-二硼基胺 [RN(BPin)]，它们与醛原位反应得到亚胺。从 N,N-二硼基胺形成亚胺不需要脱水剂，适用于广泛的 N,N-二硼基胺和醛底物，并且具有高度的化学选择性，不受各种常见官能团的影响，如烯烃、炔烃、仲胺、酮、酯、酰胺、羧酸、吡啶、腈和硝基化合物。整个转化代表了一种从腈制备亚胺的具有合成价值的方法，可以以连续一锅法进行，容忍酯、内酯、羧酰胺和未活化的烯烃官能团。
