Synthesis 2017; 49(04): 736-744
DOI: 10.1055/s-0036-1588345
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© Georg Thieme Verlag Stuttgart · New York

Borinic Acids via Direct Arylation of Amine–Borane Complexes: An Air- and Water-Stable Boron Source

Jimmy Richard
Institut des Sciences Moléculaires, UMR 5255 CNRS - Université de Bordeaux, 351 cours de la libération, 33405 Talence cedex, France   Email: sandra.pinet@u-bordeaux.fr   Email: mathieu.pucheault@u-bordeaux.fr
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Mélodie Birepinte
Institut des Sciences Moléculaires, UMR 5255 CNRS - Université de Bordeaux, 351 cours de la libération, 33405 Talence cedex, France   Email: sandra.pinet@u-bordeaux.fr   Email: mathieu.pucheault@u-bordeaux.fr
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Jean Baptiste Charbonnier
Institut des Sciences Moléculaires, UMR 5255 CNRS - Université de Bordeaux, 351 cours de la libération, 33405 Talence cedex, France   Email: sandra.pinet@u-bordeaux.fr   Email: mathieu.pucheault@u-bordeaux.fr
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Virginie Liautard
Institut des Sciences Moléculaires, UMR 5255 CNRS - Université de Bordeaux, 351 cours de la libération, 33405 Talence cedex, France   Email: sandra.pinet@u-bordeaux.fr   Email: mathieu.pucheault@u-bordeaux.fr
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Sandra Pinet*
Institut des Sciences Moléculaires, UMR 5255 CNRS - Université de Bordeaux, 351 cours de la libération, 33405 Talence cedex, France   Email: sandra.pinet@u-bordeaux.fr   Email: mathieu.pucheault@u-bordeaux.fr
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Mathieu Pucheault*
Institut des Sciences Moléculaires, UMR 5255 CNRS - Université de Bordeaux, 351 cours de la libération, 33405 Talence cedex, France   Email: sandra.pinet@u-bordeaux.fr   Email: mathieu.pucheault@u-bordeaux.fr
› Author Affiliations
Further Information

Publication History

Received: 07 October 2016

Accepted: 13 October 2016

Publication Date:
15 November 2016 (online)

Abstract

A synthesis of borinic acids and borinates was optimized using amine–borane complexes as a water and air insensitive borylating agent. The reaction operates under convenient conditions using a non-cryogenic temperature and with no flash chromatography, and it gives no boron impurities. The reaction proceeds through a tandem dehydrogenation–double addition mechanism.

Supporting Information

 
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