Literature DB >> 11671754

Lewis Acid-Promoted Coupling Reactions of Acid Chlorides with Organoaluminum and Organozinc Reagents.

Mitsuhiro Arisawa1, Yasuhiro Torisawa, Michiaki Kawahara, Masamichi Yamanaka, Atsushi Nishida, Masako Nakagawa.   

Abstract

An efficient synthesis of alpha,beta-unsaturated ketones by the reaction of acid chlorides with trialkylaluminum (1/3 mole equiv) in the presence of AlCl(3) (1 mol equiv) is described. Dialkylzincs were also useful and are easier to prepare than trialkylaluminum. Reaction of RCOCl with R'AlCl(2) or R'(2)AlCl gave R'COR, without AlCl(3), in high yield.

Entities:  

Year:  1997        PMID: 11671754     DOI: 10.1021/jo970244a

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  2 in total

1.  Acylation of N-p-Toluenesulfonylpyrrole Under Friedel-Crafts Conditions. Evidence for Organoaluminum Intermediates.

Authors:  John W Huffman; Valerie J Smith; Lea W Padgett
Journal:  Tetrahedron       Date:  2008-02-25       Impact factor: 2.457

2.  Continuous flow synthesis of diaryl ketones by coupling of aryl Grignard reagents with acyl chlorides under mild conditions in the ecofriendly solvent 2-methyltetrahydrofuran.

Authors:  Chuan-Tao Zhang; Rui Zhu; Zheng Wang; Bing Ma; Adrian Zajac; Marcin Smiglak; Chun-Nian Xia; Steven L Castle; Wen-Long Wang
Journal:  RSC Adv       Date:  2019-01-17       Impact factor: 3.361

  2 in total

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