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Cobalt-Catalyzed Deoxygenative Hydroboration of Nitro Compounds and Applications to One-Pot Synthesis of Aldimines and Amides
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2021-11-03 , DOI: 10.1002/adsc.202101043
Kristina Gudun 1 , Raikhan Zakarina 1 , Medet Segizbayev 2 , Davit Hayrapetyan 1 , Ainur Slamova 1 , Andrey Khalimon 1
Affiliation  

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.

中文翻译:

硝基化合物的钴催化脱氧硼氢化反应及其在醛亚胺和酰胺的一锅法合成中的应用

使用与双[(2-二苯基膦基)苯基]醚 (dpephos) 连接的可商购且台式稳定的 Co(acac) 2与 HBPin 选择性室温硼氢化硝基化合物(TOF 高达 4615 h -1),耐受卤化物、羟基、氨基、醚、酯、内酯、酰胺和杂芳族官能团。这些反应提供了直接获得各种原位N-硼胺 RN(H)BPin的途径用醛和羧酸处理产生一系列醛亚胺和仲羧酰胺,而不需要脱水和/或偶联剂。以顺序一锅法将这些转化结合起来,可以从容易获得且廉价的硝基化合物直接和选择性地合成醛亚胺和仲羧酰胺。
更新日期:2021-11-03
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