Cobalt‐Catalyzed Deoxygenative Hydroboration of Nitro Compounds and Applications to One‐Pot Synthesis of Aldimines and Amides

2021

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DOI 10.1002/adsc.202101043
Data confidence 85 high
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Abstract

Abstract The commercially available and bench‐stable Co(acac) 2 ligated with bis[(2‐diphenylphosphino)phenyl] ether (dpephos) was employed for selective room temperature hydroboration of nitro compounds with HBPin (TOF up to 4615 h −1 ), tolerating halide, hydroxy, amino, ether, ester, lactone, amide and heteroaromatic functionalities. These reactions offered a direct access to a variety of N ‐borylamines RN(H)BPin, which were in situ treated with aldehydes and carboxylic acids to produce a series of aldimines and secondary carboxamides without the need for dehydrating and/or coupling reagents. Combination of these transformations in a sequential one‐pot manner allowed for direct and selective synthesis of aldimines and secondary carboxamides from readily available and inexpensive nitro compounds. magnified image