Literature DB >> 19354317

Selective monomethylation of anilines by Cu(OAc)2-promoted cross-coupling with MeB(OH)2.

Israel González1, Jesús Mosquera, César Guerrero, Ramón Rodríguez, Jacobo Cruces.   

Abstract

N-Methylanilines are readily synthesized in high yields through the copper(II)-promoted coupling of anilines and methylboronic acid. This method represents a new approach for the selective monomethylation of anilines, and it is the first reported example of a Chan-Lam coupling involving the use of methylboronic acid. An incubation period of the substrate with the copper reagent is needed before addition of the methylboronic acid.

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Year:  2009        PMID： 19354317     DOI： 10.1021/ol802882k

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


  10 in total

1.  Copper-Catalyzed Amidation of Primary and Secondary Alkyl Boronic Esters.

Authors:  Luis M Mori-Quiroz; Kirk W Shimkin; Sina Rezazadeh; Ryan A Kozlowski; Donald A Watson
Journal:  Chemistry       Date:  2016-09-22       Impact factor: 5.236

2.  Dirhodium-catalyzed C-H arene amination using hydroxylamines.

Authors:  Mahesh P Paudyal; Adeniyi Michael Adebesin; Scott R Burt; Daniel H Ess; Zhiwei Ma; László Kürti; John R Falck
Journal:  Science       Date:  2016-09-09       Impact factor: 47.728

3.  Development and characterization of 3-(benzylsulfonamido)benzamides as potent and selective SIRT2 inhibitors.

Authors:  Mohammad A Khanfar; Luisa Quinti; Hua Wang; Soo Hyuk Choi; Aleksey G Kazantsev; Richard B Silverman
Journal:  Eur J Med Chem       Date:  2014-02-06       Impact factor: 6.514

4.  From methylene bridged diindole to carbonyl linked benzimidazoleindole: Development of potent and metabolically stable PCSK9 modulators.

Authors:  Haibo Xie; Ka Yang; Gabrielle N Winston-McPherson; Donnie S Stapleton; Mark P Keller; Alan D Attie; Kerry A Smith; Weiping Tang
Journal:  Eur J Med Chem       Date:  2020-08-04       Impact factor: 6.514

5.  Copper-Catalyzed Chan-Lam Cyclopropylation of Phenols and Azaheterocycles.

Authors:  Joseph Derosa; Miriam L O'Duill; Matthew Holcomb; Mark N Boulous; Ryan L Patman; Fen Wang; Michelle Tran-Dubé; Indrawan McAlpine; Keary M Engle
Journal:  J Org Chem       Date:  2018-03-13       Impact factor: 4.354

6.  Evidence for alkene cis-aminocupration, an aminooxygenation case study: kinetics, EPR spectroscopy, and DFT calculations.

Authors:  Monissa C Paderes; Lee Belding; Branden Fanovic; Travis Dudding; Jerome B Keister; Sherry R Chemler
Journal:  Chemistry       Date:  2012-01-11       Impact factor: 5.236

7.  Selective formation of secondary amides via the copper-catalyzed cross-coupling of alkylboronic acids with primary amides.

Authors:  Steven A Rossi; Kirk W Shimkin; Qun Xu; Luis M Mori-Quiroz; Donald A Watson
Journal:  Org Lett       Date:  2013-04-23       Impact factor: 6.005

8.  Stereoselective oxidative glycosylation of anomeric nucleophiles with alcohols and carboxylic acids.

Authors:  Tianyi Yang; Feng Zhu; Maciej A Walczak
Journal:  Nat Commun       Date:  2018-09-07       Impact factor: 14.919

9.  Selective Pd-Catalyzed Monoarylation of Small Primary Alkyl Amines through Backbone-Modification in Ylide-Functionalized Phosphines (YPhos).

Authors:  Ilja Rodstein; Daniel Sowa Prendes; Leon Wickert; Maurice Paaßen; Viktoria H Gessner
Journal:  J Org Chem       Date:  2020-09-21       Impact factor: 4.354

10.  Synthesis of Mono-N-Methyl Aromatic Amines from Nitroso Compounds and Methylboronic Acid.

Authors:  Silvia Roscales; Aurelio G Csákÿ
Journal:  ACS Omega       Date:  2019-08-12
  10 in total

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