Literature DB >> 23098335

Nickel-catalyzed synthesis of diarylamines via oxidatively induced C-N bond formation at room temperature.

Laurean Ilies1, Tatsuaki Matsubara, Eiichi Nakamura.   

Abstract

A nickel-catalyzed oxidative coupling of zinc amides with organomagnesium compounds selectively produces diarylamines under mild reaction conditions, with tolerance for chloride, bromide, hydroxyl, ester, and ketone groups. A diamine is bis-monoarylated. A bromoaniline undergoes N-arylation followed by Kumada-Tamao-Corriu coupling in one pot. The reaction may proceed via oxidatively induced reductive elimination of a nickel species.

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Year:  2012        PMID： 23098335     DOI： 10.1021/ol302688u

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


  10 in total

1.  Electrochemically Enabled, Nickel-Catalyzed Amination.

Authors:  Chao Li; Yu Kawamata; Hugh Nakamura; Julien C Vantourout; Zhiqing Liu; Qinglong Hou; Denghui Bao; Jeremy T Starr; Jinshan Chen; Ming Yan; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-14       Impact factor: 15.336

2.  Cu(II) complex of pyridine-based polydentate as a novel, efficient, and highly reusable catalyst in C-N bond-forming reaction.

Authors:  Hashem Sharghi; Saeideh Sepehri; Mahdi Aberi
Journal:  Mol Divers       Date:  2017-06-26       Impact factor: 2.943

3.  Electrochemically Driven, Ni-Catalyzed Aryl Amination: Scope, Mechanism, and Applications.

Authors:  Yu Kawamata; Julien C Vantourout; David P Hickey; Peng Bai; Longrui Chen; Qinglong Hou; Wenhua Qiao; Koushik Barman; Martin A Edwards; Alberto F Garrido-Castro; Justine N deGruyter; Hugh Nakamura; Kyle Knouse; Chuanguang Qin; Khalyd J Clay; Denghui Bao; Chao Li; Jeremy T Starr; Carmen Garcia-Irizarry; Neal Sach; Henry S White; Matthew Neurock; Shelley D Minteer; Phil S Baran
Journal:  J Am Chem Soc       Date:  2019-04-02       Impact factor: 15.419

4.  Photochemically-Mediated, Nickel-Catalyzed Synthesis of N-(Hetero)aryl Sulfamate Esters.

Authors:  J Miles Blackburn; Anastasia L Gant Kanegusuku; Georgia E Scott; Jennifer L Roizen
Journal:  Org Lett       Date:  2019-08-22       Impact factor: 6.005

5.  Aryl amination using ligand-free Ni(II) salts and photoredox catalysis.

Authors:  Emily B Corcoran; Michael T Pirnot; Shishi Lin; Spencer D Dreher; Daniel A DiRocco; Ian W Davies; Stephen L Buchwald; David W C MacMillan
Journal:  Science       Date:  2016-06-23       Impact factor: 47.728

6.  Iron-catalyzed arylation of heterocycles via directed C-H bond activation.

Authors:  John J Sirois; Riley Davis; Brenton DeBoef
Journal:  Org Lett       Date:  2014-01-22       Impact factor: 6.005

7.  Controlling first-row catalysts: amination of aryl and heteroaryl chlorides and bromides with primary aliphatic amines catalyzed by a BINAP-ligated single-component Ni(0) complex.

Authors:  Shaozhong Ge; Rebecca A Green; John F Hartwig
Journal:  J Am Chem Soc       Date:  2014-01-21       Impact factor: 15.419

8.  Versatile routes for synthesis of diarylamines through acceptorless dehydrogenative aromatization catalysis over supported gold-palladium bimetallic nanoparticles.

Authors:  Kento Taniguchi; Xiongjie Jin; Kazuya Yamaguchi; Kyoko Nozaki; Noritaka Mizuno
Journal:  Chem Sci       Date:  2016-12-01       Impact factor: 9.825

9.  Chromium-catalyzed para-selective formation of quaternary carbon centers by alkylation of benzamide derivatives.

Authors:  Pei Liu; Changpeng Chen; Xuefeng Cong; Jinghua Tang; Xiaoming Zeng
Journal:  Nat Commun       Date:  2018-11-06       Impact factor: 14.919

10.  Chemoselective, Scalable Nickel-Electrocatalytic O-Arylation of Alcohols.

Authors:  Hai-Jun Zhang; Longrui Chen; Martins S Oderinde; Jacob T Edwards; Yu Kawamata; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2021-08-15       Impact factor: 16.823
  10 in total

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