Literature DB >> 25162768

Direct arylation of C(sp3)-H bonds in aliphatic amides with diaryliodonium salts in the presence of a nickel catalyst.

Miki Iyanaga1, Yoshinori Aihara, Naoto Chatani.   

Abstract

The Ni(II)-catalyzed direct arylation of C(sp(3))-H (methyl and methylene) bonds in aliphatic amides containing an 8-aminoquinoline moiety as the directing group with diaryliodonium salts as coupling electrophiles is described. A wide variety of functional groups are tolerated in the reaction. The reaction represents the first example of the Ni-catalyzed direct arylation of C(sp(3))-H bonds with diaryliodonium salts.

Entities:  

Year:  2014        PMID: 25162768     DOI: 10.1021/jo501691f

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  12 in total

Review 1.  Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)-H Bonds.

Authors:  Bin Liu; Andrew M Romine; Camille Z Rubel; Keary M Engle; Bing-Feng Shi
Journal:  Chem Rev       Date:  2021-10-29       Impact factor: 60.622

2.  A Mild and General One-Pot Synthesis of Densely Functionalized Diaryliodonium Salts.

Authors:  Linlin Qin; Bao Hu; Kiel D Neumann; Ethan J Linstad; Katelyenn McCauley; Jordan Veness; Jayson J Kempinger; Stephen G DiMagno
Journal:  European J Org Chem       Date:  2015-08-14

3.  Palladium-Catalyzed Directed C(sp3)-H Arylation of Saturated Heterocycles at C-3 Using a Concise Optimization Approach.

Authors:  Dominic P Affron; James A Bull
Journal:  European J Org Chem       Date:  2015-11-27

4.  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

5.  TBAI-Catalyzed Oxidative Coupling of Benzyl Ketones to Synthesize 2,3-Diaryl-1,4-Diketones in Water.

Authors:  Lingkai Kong; Xueping Hu; Li-Ping Bai
Journal:  ACS Omega       Date:  2022-01-07

6.  Ni(ii)-catalyzed mono-selective ortho-arylation of unactivated aryl C-H bonds utilizing amino acids as a directing group.

Authors:  Zhanqing Cong; Feng Gao; Hong Liu
Journal:  RSC Adv       Date:  2019-04-08       Impact factor: 4.036

7.  Synthesis of β-arylated alkylamides via Pd-catalyzed one-pot installation of a directing group and C(sp(3))-H arylation.

Authors:  Yunyun Liu; Yi Zhang; Xiaoji Cao; Jie-Ping Wan
Journal:  Beilstein J Org Chem       Date:  2016-06-03       Impact factor: 2.883

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

9.  Palladium-catalyzed direct β-arylation of ketones with diaryliodonium salts: a stoichiometric heavy metal-free and user-friendly approach.

Authors:  Zhongxing Huang; Quynh P Sam; Guangbin Dong
Journal:  Chem Sci       Date:  2015-06-17       Impact factor: 9.825

10.  4-Methyltetrahydropyran (4-MeTHP): Application as an Organic Reaction Solvent.

Authors:  Shoji Kobayashi; Tomoki Tamura; Saki Yoshimoto; Takashi Kawakami; Araki Masuyama
Journal:  Chem Asian J       Date:  2019-10-16
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