Literature DB >> 23734676

Simple and sustainable iron-catalyzed aerobic C-H functionalization of N,N-dialkylanilines.

Maxim O Ratnikov1, Xinfang Xu, Michael P Doyle.   

Abstract

Iron(III) chloride catalyzes the aerobic oxidation of tertiary anilines, including tetrahydroisoquinolines, to form reactive iminium ion intermediates that undergo Mannich reactions with silyloxyfurans, nitroalkanes, and other nucleophiles to give the corresponding butenolides, nitro compounds, and α-substituted tetrahydroisoquinolines, respectively, in good to excellent yields.

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Year:  2013        PMID: 23734676     DOI: 10.1021/ja402479r

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  8 in total

1.  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

2.  α-Arylation of Saturated Azacycles and N-Methylamines via Palladium(II)-Catalyzed C(sp(3))-H Coupling.

Authors:  Jillian E Spangler; Yoshihisa Kobayashi; Pritha Verma; Dong-Hui Wang; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2015-09-10       Impact factor: 15.419

3.  Synthesis of (±)-Tetrabenazine by Visible Light Photoredox Catalysis.

Authors:  Lindsey R Orgren; Emily E Maverick; Christopher C Marvin
Journal:  J Org Chem       Date:  2015-11-13       Impact factor: 4.354

4.  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

5.  The redox-Mannich reaction.

Authors:  Weijie Chen; Daniel Seidel
Journal:  Org Lett       Date:  2014-05-23       Impact factor: 6.005

6.  Oxidative diversification of amino acids and peptides by small-molecule iron catalysis.

Authors:  Thomas J Osberger; Donald C Rogness; Jeffrey T Kohrt; Antonia F Stepan; M Christina White
Journal:  Nature       Date:  2016-08-01       Impact factor: 49.962

7.  Sustainable Synthetic Approach for (Pyrazol-4-ylidene)pyridines By Metal Catalyst-Free Aerobic C(sp2)-C(sp3) Coupling Reactions between 1-Amino-2-imino-pyridines and 1-Aryl-5-pyrazolones.

Authors:  Hamada Mohamed Ibrahim; Haider Behbehani
Journal:  ACS Omega       Date:  2019-07-05

8.  Oxidative Dearomative Cross-Dehydrogenative Coupling of Indoles with Diverse C-H Nucleophiles: Efficient Approach to 2,2-Disubstituted Indolin-3-ones.

Authors:  Xue Yan; Ying-De Tang; Cheng-Shi Jiang; Xigong Liu; Hua Zhang
Journal:  Molecules       Date:  2020-01-20       Impact factor: 4.411

  8 in total

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