Cobalt‐Catalyzed Deoxygenative Hydroboration of Nitro Compounds and Applications to One‐Pot Synthesis of Aldimines and Amides. Issue 3 (23rd November 2021)

• Record Type: Journal Article
• Authors: Gudun, Kristina A.; Zakarina, Raikhan; Segizbayev, Medet; Hayrapetyan, Davit; Slamova, Ainur; Khalimon, Andrey Y.
• Is Part Of: Advanced synthesis & catalysis. Volume 364:Issue 3(2022)
• Page Start: 601
• Page End: 611
• Publication Date: 2021-11-23
• Subjects: Cobalt -- Hydroboration -- Nitro compounds -- Aminoboranes -- C−N bond formation; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202101043
• Languages: English
• ISSNs: 1615-4150

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. Abstract :