Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 22, Pages 4963-4968Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202000753
Keywords
aminoboranes; cobalt; hydroboration; imines; nitriles
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Funding
- Nazarbayev University through NU-ORAU grant [2016023]
- Nazarbayev University through FDCRG grant [240919FD3911]
- SPG grant
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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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