Literature DB >> 25333482

Nickel-catalyzed reductive methylation of alkyl halides and acid chlorides with methyl p-tosylate.

Zhuye Liang1, Weichao Xue, Kunhua Lin, Hegui Gong.   

Abstract

Methylation of unactivated alkyl halides and acid chlorides under Ni-catalyzed reductive coupling conditions led to efficient formation of methylated alkanes and ketones using methyl p-methyl tosylate as the methylation reagent. Moderate to excellent coupling yields as well as excellent functional group tolerance were observed under the present mild and easy-to-operate reaction conditions.

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Year:  2014        PMID： 25333482     DOI： 10.1021/ol502682q

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


  20 in total

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Journal:  J Am Chem Soc       Date:  2018-12-10       Impact factor: 15.419

2.  Cross-Electrophile Coupling of Vinyl Halides with Alkyl Halides.

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Journal:  Chemistry       Date:  2016-04-28       Impact factor: 5.236

3.  Nickel/Photoredox-Catalyzed Methylation of (Hetero)aryl Chlorides Using Trimethyl Orthoformate as a Methyl Radical Source.

Authors:  Stavros K Kariofillis; Benjamin J Shields; Makeda A Tekle-Smith; Michael J Zacuto; Abigail G Doyle
Journal:  J Am Chem Soc       Date:  2020-04-10       Impact factor: 15.419

4.  Cross-Electrophile Coupling of Unactivated Alkyl Chlorides.

Authors:  Holt A Sakai; Wei Liu; Chi Chip Le; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2020-06-26       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 Alkyl-Alkyl Cross-Electrophile Coupling Reaction of 1,3-Dimesylates for the Synthesis of Alkylcyclopropanes.

Authors:  Amberly B Sanford; Taylor A Thane; Tristan M McGinnis; Pan-Pan Chen; Xin Hong; Elizabeth R Jarvo
Journal:  J Am Chem Soc       Date:  2020-03-04       Impact factor: 15.419

7.  Harnessing Alkyl Amines as Electrophiles for Nickel-Catalyzed Cross Couplings via C-N Bond Activation.

Authors:  Corey H Basch; Jennie Liao; Jianyu Xu; Jacob J Piane; Mary P Watson
Journal:  J Am Chem Soc       Date:  2017-04-05       Impact factor: 15.419

8.  Alcohols as Latent Coupling Fragments for Metallaphotoredox Catalysis: sp3-sp2 Cross-Coupling of Oxalates with Aryl Halides.

Authors:  Xiaheng Zhang; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2016-10-17       Impact factor: 15.419

9.  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

10.  Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Chlorides with Primary Alkyl Chlorides.

Authors:  Seoyoung Kim; Matthew J Goldfogel; Michael M Gilbert; Daniel J Weix
Journal:  J Am Chem Soc       Date:  2020-05-21       Impact factor: 15.419
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