Literature DB >> 23802908

Primary alkylboronic acids as highly active catalysts for the dehydrative amide condensation of α-hydroxycarboxylic acids.

Risa Yamashita1, Akira Sakakura, Kazuaki Ishihara.   

Abstract

Primary alkylboronic acids such as methylboronic acid and butylboronic acid are highly active catalysts for the dehydrative amide condensation of α-hydroxycarboxylic acids. The catalytic activities of these primary alkylboronic acids are much higher than those of the previously reported arylboronic acids. The present method was easily applied to a large-scale synthesis, and 14 g of an amide was obtained in a single reaction.

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Year:  2013        PMID: 23802908     DOI: 10.1021/ol401537f

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  6 in total

1.  Unique physicochemical and catalytic properties dictated by the B3NO2 ring system.

Authors:  Hidetoshi Noda; Makoto Furutachi; Yasuko Asada; Masakatsu Shibasaki; Naoya Kumagai
Journal:  Nat Chem       Date:  2017-01-30       Impact factor: 24.427

2.  Mechanistic insights into boron-catalysed direct amidation reactions.

Authors:  Sergey Arkhipenko; Marco T Sabatini; Andrei S Batsanov; Valerija Karaluka; Tom D Sheppard; Henry S Rzepa; Andrew Whiting
Journal:  Chem Sci       Date:  2018-01-02       Impact factor: 9.825

3.  Boronic acid-DMAPO cooperative catalysis for dehydrative condensation between carboxylic acids and amines.

Authors:  Kazuaki Ishihara; Yanhui Lu
Journal:  Chem Sci       Date:  2015-11-06       Impact factor: 9.825

4.  Catalytic direct amidations in tert-butyl acetate using B(OCH2CF3)3.

Authors:  Charlotte E Coomber; Victor Laserna; Liam T Martin; Peter D Smith; Helen C Hailes; Michael J Porter; Tom D Sheppard
Journal:  Org Biomol Chem       Date:  2019-06-21       Impact factor: 3.876

5.  Methyltrimethoxysilane (MTM) as a Reagent for Direct Amidation of Carboxylic Acids.

Authors:  D Christopher Braddock; Joshua J Davies; Paul D Lickiss
Journal:  Org Lett       Date:  2022-01-27       Impact factor: 6.005

Review 6.  Catalytic and non-catalytic amidation of carboxylic acid substrates.

Authors:  Keyvan Pedrood; Saeed Bahadorikhalili; Vahid Lotfi; Bagher Larijani; Mohammad Mahdavi
Journal:  Mol Divers       Date:  2021-06-13       Impact factor: 2.943

  6 in total

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