Literature DB >> 26821872

Phenyltrimethylammonium Salts as Methylation Reagents in the Nickel-Catalyzed Methylation of C-H Bonds.

Takeshi Uemura1, Mao Yamaguchi1, Naoto Chatani2.   

Abstract

Methylation of C(sp(2))-H bonds was achieved through the Ni(II)-catalyzed reaction of benzamides with phenyltrimethylammonium bromide or iodide as the source of the methyl group. The reaction has a broad scope and shows high functional-group compatibility. The reaction is also applicable to the methylation of C(sp(3))-H bonds in aliphatic amides.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H activation; chelation assistance; methylation; nickel; phenyltrimethylammonium iodide

Year:  2016        PMID： 26821872     DOI： 10.1002/anie.201511197

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  10 in total

1.  The mechanism of directed Ni(ii)-catalyzed C-H iodination with molecular iodine.

Authors:  Brandon E Haines; Jin-Quan Yu; Djamaladdin G Musaev
Journal:  Chem Sci       Date:  2017-11-28       Impact factor: 9.825

Review 2.  σ-Noninnocence: Masked Phenyl-Cation Transfer at Formal NiIV.

Authors:  Jelte S Steen; Gerald Knizia; Johannes E M N Klein
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-15       Impact factor: 15.336

3.  Nickela-electrocatalyzed Mild C-H Alkylations at Room Temperature.

Authors:  Ramesh C Samanta; Julia Struwe; Lutz Ackermann
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-08       Impact factor: 15.336

4.  Selective α-Methylation of Aryl Ketones Using Quaternary Ammonium Salts as Solid Methylating Agents.

Authors:  Johanna Templ; Michael Schnürch
Journal:  J Org Chem       Date:  2022-03-07       Impact factor: 4.354

5.  From aniline to phenol: carbon-nitrogen bond activation via uranyl photoredox catalysis.

Authors:  Deqing Hu; Yilin Zhou; Xuefeng Jiang
Journal:  Natl Sci Rev       Date:  2021-08-20       Impact factor: 23.178

6.  Palladium-catalyzed nucleomethylation of alkynes for synthesis of methylated heteroaromatic compounds.

Authors:  Xi Yang; Gang Wang; Zhi-Shi Ye
Journal:  Chem Sci       Date:  2022-08-18       Impact factor: 9.969

7.  Stille coupling via C-N bond cleavage.

Authors:  Dong-Yu Wang; Masatoshi Kawahata; Ze-Kun Yang; Kazunori Miyamoto; Shinsuke Komagawa; Kentaro Yamaguchi; Chao Wang; Masanobu Uchiyama
Journal:  Nat Commun       Date:  2016-09-30       Impact factor: 14.919

8.  Nickel-catalyzed C-H/N-H annulation of aromatic amides with alkynes in the absence of a specific chelation system.

Authors:  Atsushi Obata; Yusuke Ano; Naoto Chatani
Journal:  Chem Sci       Date:  2017-07-24       Impact factor: 9.825

Review 9.  High-Valent NiIII and NiIV Species Relevant to C-C and C-Heteroatom Cross-Coupling Reactions: State of the Art.

Authors:  Noel Nebra
Journal:  Molecules       Date:  2020-03-04       Impact factor: 4.411

10.  Modular and regioselective synthesis of all-carbon tetrasubstituted olefins enabled by an alkenyl Catellani reaction.

Authors:  Jianchun Wang; Zhe Dong; Cheng Yang; Guangbin Dong
Journal:  Nat Chem       Date:  2019-11-18       Impact factor: 24.427
  10 in total

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