Literature DB >> 22684052

Mild ketone formation via Ni-catalyzed reductive coupling of unactivated alkyl halides with acid anhydrides.

Hongyu Yin1, Chenglong Zhao, Hengzhi You, Kunhua Lin, Hegui Gong.   

Abstract

Ni-catalyzed ketone formation through mild reductive coupling of a diverse set of unactivated alkyl bromides and iodides with particularly aryl acid anhydrides was successfully developed using zinc as the terminal reductant. These conditions also allow direct coupling of alkyl iodides with aryl acids in the presence of Boc(2)O and MgCl(2).

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Year:  2012        PMID： 22684052     DOI： 10.1039/c2cc33232a

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  17 in total

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Authors:  Shengyang Ni; Natalia M Padial; Cian Kingston; Julien C Vantourout; Daniel C Schmitt; Jacob T Edwards; Monika M Kruszyk; Rohan R Merchant; Pavel K Mykhailiuk; Brittany B Sanchez; Shouliang Yang; Matthew A Perry; Gary M Gallego; James J Mousseau; Michael R Collins; Robert J Cherney; Pavlo S Lebed; Jason S Chen; Tian Qin; Phil S Baran
Journal:  J Am Chem Soc       Date:  2019-04-16       Impact factor: 15.419

2.  Nickel-catalyzed cross-electrophile coupling of 2-chloropyridines with alkyl bromides.

Authors:  Daniel A Everson; Joseph A Buonomo; Daniel J Weix
Journal:  Synlett       Date:  2014-01       Impact factor: 2.454

3.  Ketones from Nickel-Catalyzed Decarboxylative, Non-Symmetric Cross-Electrophile Coupling of Carboxylic Acid Esters.

Authors:  Jiang Wang; Brian P Cary; Peyton D Beyer; Samuel H Gellman; Daniel J Weix
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-30       Impact factor: 15.336

4.  Mechanism and selectivity in nickel-catalyzed cross-electrophile coupling of aryl halides with alkyl halides.

Authors:  Soumik Biswas; Daniel J Weix
Journal:  J Am Chem Soc       Date:  2013-10-21       Impact factor: 15.419

5.  Vinyl Triflate-Aldehyde Reductive Coupling-Redox Isomerization Mediated by Formate: Rhodium-Catalyzed Ketone Synthesis in the Absence of Stoichiometric Metals.

Authors:  William G Shuler; Robert A Swyka; Tabitha T Schempp; Brian J Spinello; Michael J Krische
Journal:  Chemistry       Date:  2019-09-04       Impact factor: 5.236

6.  Nickel-Catalyzed Synthesis of Ketones from Alkyl Halides and Acid Chlorides: Preparation of Ethyl 4-Oxododecanoate.

Authors:  Alexander C Wotal; Donald C Batesky; Daniel J Weix
Journal:  Organic Synth       Date:  2016-02-22

7.  Substituted 2,2'-bipyridines by nickel-catalysis: 4,4'-di-tert-butyl-2,2'-bipyridine.

Authors:  Joseph A Buonomo; Daniel A Everson; Daniel J Weix
Journal:  Synthesis (Stuttg)       Date:  2013-11-01       Impact factor: 3.157

8.  Nickel-Catalyzed Synthesis of Dialkyl Ketones from the Coupling of N-Alkyl Pyridinium Salts with Activated Carboxylic Acids.

Authors:  Jiang Wang; Megan E Hoerrner; Mary P Watson; Daniel J Weix
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-05       Impact factor: 15.336

9.  Methods and Mechanisms for Cross-Electrophile Coupling of Csp(2) Halides with Alkyl Electrophiles.

Authors:  Daniel J Weix
Journal:  Acc Chem Res       Date:  2015-05-26       Impact factor: 22.384

10.  Light-Driven Carbene Catalysis for the Synthesis of Aliphatic and α-Amino Ketones.

Authors:  Anna V Bay; Keegan P Fitzpatrick; Gisela A González-Montiel; Abdikani Omar Farah; Paul Ha-Yeon Cheong; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2021-07-14       Impact factor: 16.823
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