Literature DB >> 11418053

Copper-catalyzed coupling of arylboronic acids and amines.

J C Antilla1, S L Buchwald.   

Abstract

[reaction: see text] A general catalytic coupling of arylboronic acids and amines is reported. This room-temperature coupling was realized through the use of catalytic copper(II) acetate, 2,6-lutidine as base, and myristic acid as an additive. Functionalized aniline substrates provided the diarylamine coupling products in good yield (58-91%). A variety of alkylamines were also successfully coupled to give N-alkyl anilines in moderate yield (50-64%).

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Year:  2001        PMID: 11418053     DOI: 10.1021/ol0160396

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


  12 in total

Review 1.  Aerobic copper-catalyzed organic reactions.

Authors:  Scott E Allen; Ryan R Walvoord; Rosaura Padilla-Salinas; Marisa C Kozlowski
Journal:  Chem Rev       Date:  2013-06-20       Impact factor: 60.622

2.  Catalytic aziridination with alcoholic substrates via a chromium tetracarbene catalyst.

Authors:  C Luke Keller; Jesse L Kern; Bradley D Terry; Sharani Roy; David M Jenkins
Journal:  Chem Commun (Camb)       Date:  2018-01-04       Impact factor: 6.222

3.  Copper(II)-Catalyzed Aminooxygenation and Carboamination of N-Aryl-2-allylanilines.

Authors:  Eric S Sherman; Sherry R Chemler
Journal:  Adv Synth Catal       Date:  2009-02-01       Impact factor: 5.837

4.  Copper-Catalyzed Synthesis of N-Aryl and N-Sulfonyl Indoles from 2-Vinylanilines with O2 as Terminal Oxidant and TEMPO as Co-Catalyst.

Authors:  Timothy W Liwosz; Sherry R Chemler
Journal:  Synlett       Date:  2014       Impact factor: 2.454

5.  N-substituted imines by the copper-catalyzed N-imination of boronic acids and organostannanes with O-acyl ketoximes.

Authors:  Songbai Liu; Ying Yu; Lanny S Liebeskind
Journal:  Org Lett       Date:  2007-04-20       Impact factor: 6.005

6.  Copper(II) carboxylate-promoted intramolecular carboamination of alkenes for the synthesis of polycyclic lactams.

Authors:  Peter H Fuller; Sherry R Chemler
Journal:  Org Lett       Date:  2007-11-29       Impact factor: 6.005

7.  Diastereoselective pyrrolidine synthesis via copper promoted intramolecular aminooxygenation of alkenes: formal synthesis of (+)-monomorine.

Authors:  Monissa C Paderes; Sherry R Chemler
Journal:  Org Lett       Date:  2009-05-07       Impact factor: 6.005

8.  N-amidation by copper-mediated cross-coupling of organostannanes or boronic acids with o-acetyl hydroxamic acids.

Authors:  Zhihui Zhang; Ying Yu; Lanny S Liebeskind
Journal:  Org Lett       Date:  2008-06-17       Impact factor: 6.005

9.  Copper-Mediated Radical-Polar Crossover Enables Photocatalytic Oxidative Functionalization of Sterically Bulky Alkenes.

Authors:  Nicholas L Reed; Grace A Lutovsky; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2021-04-15       Impact factor: 15.419

10.  N-Arylation of amines, amides, imides and sulfonamides with arylboroxines catalyzed by simple copper salt/EtOH system.

Authors:  Zhang-Guo Zheng; Jun Wen; Na Wang; Bo Wu; Xiao-Qi Yu
Journal:  Beilstein J Org Chem       Date:  2008-11-07       Impact factor: 2.883

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