Literature DB >> 29531521

Arylation of Azaarylmethylamines with Aryl Chlorides and a NiBr2/NIXANTPHOS-based Catalyst.

Gui Gao1, Yue Fu2, Minyan Li2, Bo Wang1, Bing Zheng1, Shicong Hou1, Patrick J Walsh2.   

Abstract

A nickel-catalyzed coupling of azaarylmethylamines with aryl chlorides has been achieved. NIXANTPHOS together with low cost NiBr2 was successfully developed and optimized to exhibit high reactivity at 2.5 mol % loading. Under optimized reaction conditions, aryl(azaaryl)methylamine products were afforded in good to excellent yields (22 examples, up to 98% yield).

Entities:  

Keywords:  Aryl Chlorides; Arylation; Azaarylmethylamines; NIXANTPHOS; NiBr2

Year:  2017        PMID： 29531521      PMCID： PMC5844573          DOI： 10.1002/adsc.201700438

Source DB:  PubMed          Journal:  Adv Synth Catal        ISSN： 1615-4150            Impact factor:   5.837


  37 in total

1.  Synthesis of diarylmethylamines via palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions.

Authors:  Minyan Li; Baris Yücel; Javier Adrio; Ana Bellomo; Patrick J Walsh
Journal:  Chem Sci       Date:  2014-06-01       Impact factor: 9.825

2.  Umpolung Synthesis of Diarylmethylamines via Palladium-Catalyzed Arylation of N-Benzyl Aldimines.

Authors:  Minyan Li; Baris Yucel; Jacqueline Jiménez; Madeline Rotella; Yue Fu; Patrick J Walsh
Journal:  Adv Synth Catal       Date:  2016-05-12       Impact factor: 5.837

3.  Synthesis and antitumor activity of novel N-substituted tetrahydro-β-carboline-imidazolium salt derivatives.

Authors:  Bei Zhou; Zheng-Fen Liu; Guo-Gang Deng; Wen Chen; Min-Yan Li; Li-Juan Yang; Yan Li; Xiao-Dong Yang; Hong-Bin Zhang
Journal:  Org Biomol Chem       Date:  2016-10-04       Impact factor: 3.876

4.  Stereospecific Intramolecular Arylation of 2- and 3-Pyridyl Substituted Alkylamines via Configurationally Stable α-Pyridyl Organolithiums.

Authors:  Julien Maury; Wojciech Zawodny; Jonathan Clayden
Journal:  Org Lett       Date:  2017-01-18       Impact factor: 6.005

5.  Catalytic asymmetric α-acylation of tertiary amines mediated by a dual catalysis mode: N-heterocyclic carbene and photoredox catalysis.

Authors:  Daniel A DiRocco; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2012-05-02       Impact factor: 15.419

6.  4,5-dihydroxypyrimidine carboxamides and N-alkyl-5-hydroxypyrimidinone carboxamides are potent, selective HIV integrase inhibitors with good pharmacokinetic profiles in preclinical species.

Authors:  Vincenzo Summa; Alessia Petrocchi; Victor G Matassa; Cristina Gardelli; Ester Muraglia; Michael Rowley; Odalys Gonzalez Paz; Ralph Laufer; Edith Monteagudo; Paola Pace
Journal:  J Med Chem       Date:  2006-11-16       Impact factor: 7.446

7.  Palladium-Catalyzed Benzylic C-H Arylation of Azaarylmethylamines.

Authors:  Byeong-Seon Kim; Jacqueline Jiménez; Feng Gao; Patrick J Walsh
Journal:  Org Lett       Date:  2015-11-17       Impact factor: 6.005

8.  Transition metal-catalyzed direct arylation of substrates with activated sp3-hybridized C-H bonds and some of their synthetic equivalents with aryl halides and pseudohalides.

Authors:  Fabio Bellina; Renzo Rossi
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

9.  Total Syntheses of (R)-Strongylodiols C and D.

Authors:  Feipeng Liu; Jiangchun Zhong; Shuoning Li; Minyan Li; Lin Wu; Qian Wang; Jianyou Mao; Shikuo Liu; Bing Zheng; Min Wang; Qinghua Bian
Journal:  J Nat Prod       Date:  2016-01-06       Impact factor: 4.050

Review 10.  An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles.

Authors:  Marcus Baumann; Ian R Baxendale
Journal:  Beilstein J Org Chem       Date:  2013-10-30       Impact factor: 2.883
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  4 in total

1.  Transition-Metal-Free Radical C(sp3)-C(sp2) and C(sp3)-C(sp3) Coupling Enabled by 2-Azaallyls as Super-Electron-Donors and Coupling-Partners.

Authors:  Minyan Li; Simon Berritt; Lucas Matuszewski; Guogang Deng; Ana Pascual-Escudero; Grace B Panetti; Michal Poznik; Xiaodong Yang; Jason J Chruma; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2017-10-31       Impact factor: 15.419

2.  Nickel-catalyzed enantioselective vinylation of aryl 2-azaallyl anions.

Authors:  Shengzu Duan; Guogang Deng; Yujin Zi; Xiaomei Wu; Xun Tian; Zhengfen Liu; Minyan Li; Hongbin Zhang; Xiaodong Yang; Patrick J Walsh
Journal:  Chem Sci       Date:  2021-03-26       Impact factor: 9.825

3.  Regio- and chemoselective Csp3-H arylation of benzylamines by single electron transfer/hydrogen atom transfer synergistic catalysis.

Authors:  Takafumi Ide; Joshua P Barham; Masashi Fujita; Yuji Kawato; Hiromichi Egami; Yoshitaka Hamashima
Journal:  Chem Sci       Date:  2018-09-12       Impact factor: 9.825

4.  Pd(ii)-catalyzed meta-C-H bromination and chlorination of aniline and benzoic acid derivatives.

Authors:  Hao Wang; Lei Fu; Chunlin Zhou; Gang Li
Journal:  Chem Sci       Date:  2022-07-05       Impact factor: 9.969
  4 in total

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