Literature DB >> 25397731

n-BuLi as a highly efficient precatalyst for hydrophosphonylation of aldehydes and unactivated ketones.

Chengwei Liu1, Yu Zhang1, Qinqin Qian1, Dan Yuan1, Yingming Yao1.   

Abstract

It was found for the first time that organic alkali metal compounds serve as highly efficient precatalysts for the hydrophosphonylation reactions of aldehydes and unactivated ketones with dialkyl phosphite under mild conditions. For ketone substrates, a reversible reaction was observed, and the influence of catalyst loading and reaction temperature on the reaction equilibrium was studied in detail. Overall, the hydrophosphonylation reactions catalyzed by 0.1 mol % n-BuLi were completed within 5 min for a broad range of substrates and generated a series of α-hydroxy phosphonates in high yields.

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Year:  2014        PMID: 25397731     DOI: 10.1021/ol5030713

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


  3 in total

1.  Green and Effective Preparation of α-Hydroxyphosphonates by Ecocatalysis.

Authors:  Pola Cybulska; Yves-Marie Legrand; Alicja Babst-Kostecka; Sébastien Diliberto; Anna Leśniewicz; Erwan Oliviero; Valérie Bert; Clotilde Boulanger; Claude Grison; Tomasz K Olszewski
Journal:  Molecules       Date:  2022-05-11       Impact factor: 4.927

Review 2.  Synthesis and Reactions of α-Hydroxyphosphonates.

Authors:  Zita Rádai; György Keglevich
Journal:  Molecules       Date:  2018-06-20       Impact factor: 4.411

3.  Resolution of Racemic α-Hydroxyphosphonates: Bi(OTf)3-Catalyzed Stereoselective Esterification of α-Hydroxyphosphonates with (+)-Dibenzoyl-l-tartaric Anhydride.

Authors:  Babak Kaboudin; Sajedeh Alavi; Foad Kazemi; Hiroshi Aoyama; Tsutomu Yokomatsu
Journal:  ACS Omega       Date:  2019-09-10
  3 in total

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