Cobalt‐Catalyzed Deoxygenative Hydroboration of Nitro Compounds and Applications to One‐Pot Synthesis of Aldimines and Amides
Kristina Gudun, Raikhan Zakarina, Medet Segizbayev, Davit Hayrapetyan, Ainur Slamova, Andrey Y. Khalimon
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