期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 26, 期 22, 页码 4963-4968出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202000753
关键词
aminoboranes; cobalt; hydroboration; imines; nitriles
资金
- Nazarbayev University through NU-ORAU grant [2016023]
- Nazarbayev University through FDCRG grant [240919FD3911]
- SPG grant
The commercially available and bench-stable Co(acac)(2)/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)(2)], 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.
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