Literature DB >> 16320999

Addition of grignard reagents to aryl acid chlorides: an efficient synthesis of aryl ketones.

Xiao-jun Wang1, Li Zhang, Xiufeng Sun, Yibo Xu, Dhileepkumar Krishnamurthy, Chris H Senanayake.   

Abstract

[chemical reaction: see text]. Direct addition of Grignard reagents to acid chlorides in the presence of bis[2-(N,N-dimethylamino)ethyl] ether proceeds selectively to provide aryl ketones in high yields. A possible tridentate interaction between Grignard reagents and bis[2-(N,N-dimethylamino)ethyl] ether moderates the reactivity of Grignard reagents, preventing the newly formed ketones from nucleophilic addition by Grignard reagents.

Entities:  

Year:  2005        PMID: 16320999     DOI: 10.1021/ol052150q

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


  5 in total

1.  Palladium-Catalyzed Cross-Coupling of Monochlorosilanes And Grignard Reagents.

Authors:  Bojan Vulovic; Andrew P Cinderella; Donald A Watson
Journal:  ACS Catal       Date:  2017-10-30       Impact factor: 13.084

2.  Copper-Free Alternatives to Access Ketone Building Blocks from Grignard Reagents.

Authors:  Christoph Taeschler; Eva Kirchner; Emilia Păunescu; Ulrich Mayerhöffer
Journal:  ACS Omega       Date:  2022-01-14

3.  Efficient in situ N-heterocyclic carbene palladium(ii) generated from Pd(OAc)2 catalysts for carbonylative Suzuki coupling reactions of arylboronic acids with 2-bromopyridine under inert conditions leading to unsymmetrical arylpyridine ketones: synthesis, characterization and cytotoxic activities.

Authors:  Nedra Touj; Abdullah S Al-Ayed; Mathieu Sauthier; Lamjed Mansour; Abdel Halim Harrath; Jamil Al-Tamimi; Ismail Özdemir; Sedat Yaşar; Naceur Hamdi
Journal:  RSC Adv       Date:  2018-12-05       Impact factor: 4.036

4.  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

5.  Direct Addition of Grignard Reagents to Aliphatic Carboxylic Acids Enabled by Bulky turbo-Organomagnesium Anilides.

Authors:  Kilian Colas; A Catarina V D Dos Santos; Stefanie V Kohlhepp; Abraham Mendoza
Journal:  Chemistry       Date:  2022-01-27       Impact factor: 5.020

  5 in total

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