Literature DB >> 23815788

Simple and direct sp3 C-H bond arylation of tetrahydroisoquinolines and isochromans via 2,3-dichloro-5,6-dicyano-1,4-benzoquinone oxidation under mild conditions.

Wataru Muramatsu1, Kimihiro Nakano, Chao-Jun Li.   

Abstract

The 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated sp(3) C-H bond arylation of tetrahydroisoquinolines and isochromans is described. The corresponding products were facilely synthesized via a simple nucleophilic addition reaction between readily available aryl Grignard reagents and iminium (or oxonium) cations generated in situ by DDQ oxidation of tetrahydroisoquinolines (or isochromans) under mild conditions.

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Year:  2013        PMID： 23815788     DOI： 10.1021/ol401534g

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


  10 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.  Palladium-Catalyzed Direct α-Aryation of Benzyl Thioethers with Aryl Bromides.

Authors:  Gustavo Frensch; Nusrah Hussain; Francisco A Marques; Patrick J Walsh
Journal:  Adv Synth Catal       Date:  2014-08-11       Impact factor: 5.837

3.  Redox-neutral α-arylation of amines.

Authors:  Weijie Chen; Richard G Wilde; Daniel Seidel
Journal:  Org Lett       Date:  2013-12-13       Impact factor: 6.005

Review 4.  Quinone-Catalyzed Selective Oxidation of Organic Molecules.

Authors:  Alison E Wendlandt; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2015-11-04       Impact factor: 15.336

5.  Dual C-H functionalization of N-aryl amines: synthesis of polycyclic amines via an oxidative Povarov approach.

Authors:  Chang Min; Abbas Sanchawala; Daniel Seidel
Journal:  Org Lett       Date:  2014-05-01       Impact factor: 6.005

6.  One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates.

Authors:  Joshua P Barham; Matthew P John; John A Murphy
Journal:  Beilstein J Org Chem       Date:  2014-12-12       Impact factor: 2.883

7.  Chemoselective Palladium-Catalyzed Deprotonative Arylation/[1,2]-Wittig Rearrangement of Pyridylmethyl Ethers.

Authors:  Feng Gao; Byeong-Seon Kim; Patrick J Walsh
Journal:  Chem Sci       Date:  2015-10-27       Impact factor: 9.825

8.  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

9.  From Isocyanides to Iminonitriles via Silver-mediated Sequential Insertion of C(sp3)-H Bond.

Authors:  Huiwen Chi; Hao Li; Bingxin Liu; Rongxuan Ye; Haoyang Wang; Yin-Long Guo; Qitao Tan; Bin Xu
Journal:  iScience       Date:  2019-11-01

10.  Cross-dehydrogenative coupling and oxidative-amination reactions of ethers and alcohols with aromatics and heteroaromatics.

Authors:  Mahesh K Lakshman; Prasanna K Vuram
Journal:  Chem Sci       Date:  2017-06-30       Impact factor: 9.825
  10 in total

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