Literature DB >> 12670223

The Barbier-Grignard-type carbonyl alkylation using unactivated alkyl halides in water.

Charlene C K Keh1, Chunmei Wei, Chao-Jun Li.   

Abstract

The aqueous Barbier-Grignard-type alkylation of aldehydes with unactivated alkyl iodides and bromides was developed. By using a combination of zinc and cuprous iodide, catalyzed by indium(I) chloride, we successfully added tertiary, secondary, and primary alkyl halides to various aromatic aldehydes in 0.07 M aqueous Na2C2O4. A mechanistic rationale for the success of the reaction has been proposed.

Entities:  

Year:  2003        PMID: 12670223     DOI: 10.1021/ja029649p

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  4 in total

1.  Direct Synthesis of Secondary Benzylic Alcohols Enabled by Photoredox/Ni Dual-Catalyzed Cross-Coupling.

Authors:  Rauful Alam; Gary A Molander
Journal:  J Org Chem       Date:  2017-11-27       Impact factor: 4.354

Review 2.  En route to metal-mediated and metal-catalysed reactions in water.

Authors:  Feng Zhou; Chao-Jun Li
Journal:  Chem Sci       Date:  2018-11-05       Impact factor: 9.825

3.  Na@SiO2-Mediated Addition of Organohalides to Carbonyl Compounds for the Formation of Alcohols and Epoxides.

Authors:  Mohit Kapoor; Jih Ru Hwu
Journal:  Sci Rep       Date:  2016-11-17       Impact factor: 4.379

4.  Water opens the door to organolithiums and Grignard reagents: exploring and comparing the reactivity of highly polar organometallic compounds in unconventional reaction media towards the synthesis of tetrahydrofurans.

Authors:  Luciana Cicco; Stefania Sblendorio; Rosmara Mansueto; Filippo M Perna; Antonio Salomone; Saverio Florio; Vito Capriati
Journal:  Chem Sci       Date:  2015-11-03       Impact factor: 9.825

  4 in total

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