Magnesium promoted autocatalytic dehydrogenation of amine borane complexes: A reliable, non-cryogenic, scalable access to boronic acids

TETRAHEDRON

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Article

Marciasini, Ludovic D.¹  Richard, Jimmy¹  Cacciuttolo, Bastien¹  Sartori, Guillaume¹  Birepinte, Melodie¹  Chabaud, Laurent¹  Pinet, Sandra¹  Pucheault, Mathieu¹ 

[1] Univ Bordeaux, CNRS, Inst Sci Mol, UMR 5255, 351 Cours Liberat, F-33405 Talence, France

关键词: Borane;    Boronic acids;    Dehydrogenation;    Tandem reaction;    Magnesium;   

DOI  :  10.1016/j.tet.2018.11.036

来源: Elsevier

【 摘 要 】

Owing to the unusual reactivity of dialkylamine-borane complexes, a methodology was developed to simply access boronic acids. The intrinsic instability of magnesium aminoborohydride was tweaked into a tandem dehydrogenation borylation sequence. Proceeding via an autocatalytic cycle, amineborane dehydrogenation was induced by a variety of Grignard reagents. Overall, addition of the organo-magnesium species onto specially designed dialkylamine-borane complexes led to a variety of boronic acids in high yields. In addition, the reaction can be performed under Barbier conditions, on a large scale. (C) 2018 Elsevier Ltd. All rights reserved.

【 授权许可】

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