Literature DB >> 17165922

Copper-catalyzed amidation of allylic and benzylic C-H bonds.

Guillaume Pelletier1, David A Powell.   

Abstract

[Structure: see text] A copper-catalyzed amidation of allylic and benzylic C-H bonds with both primary and secondary sulfonamides is described. The reaction is applicable to the coupling of a diverse set of hydrocarbon species with aryl, heteroaryl, and alkyl sulfonamides and is tolerant of a variety of functional groups. Mechanistic insight has been gained through the isolation of a benzylic acetate intermediate, which was demonstrated to undergo facile conversion to the substituted sulfonamide product under copper catalysis.

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Year:  2006        PMID: 17165922     DOI: 10.1021/ol062514u

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


  16 in total

1.  Palladium(0)-catalyzed intermolecular amination of unactivated C(sp³)-H bonds.

Authors:  Jun Pan; Mingjuan Su; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2011-08-02       Impact factor: 15.336

2.  Radical C(sp3)-H functionalization and cross-coupling reactions.

Authors:  Dung L Golden; Sung-Eun Suh; Shannon S Stahl
Journal:  Nat Rev Chem       Date:  2022-05-17       Impact factor: 34.571

3.  Mechanistic Studies on the Synthesis of Pyrrolidines and Piperidines via Copper-Catalyzed Intramolecular C-H Amination.

Authors:  José María Muñoz-Molina; Daniel Bafaluy; Ignacio Funes-Ardoiz; Adiran de Aguirre; Feliu Maseras; Tomás R Belderrain; Pedro J Pérez; Kilian Muñiz
Journal:  Organometallics       Date:  2022-04-29       Impact factor: 3.837

4.  Metal-Catalyzed and Metal-Free Intermolecular Amination of Light Alkanes and Benzenes.

Authors:  Pericles Stavropoulos
Journal:  Comments Mod Chem A Comments Inorg Chem       Date:  2016-04-29       Impact factor: 4.533

5.  Oxidative Cyclization of Sulfamate Esters Using NaOCl - A Metal-Mediated Hoffman-Löffler Freytag Reaction.

Authors:  David N Zalatan; J Du Bois
Journal:  Synlett       Date:  2009-01-01       Impact factor: 2.454

6.  Copper-Catalyzed C-H Fluorination/Functionalization Sequence Enabling Benzylic C-H Cross Coupling with Diverse Nucleophiles.

Authors:  Aristidis Vasilopoulos; Dung L Golden; Joshua A Buss; Shannon S Stahl
Journal:  Org Lett       Date:  2020-07-29       Impact factor: 6.005

7.  Ph3P/CCl4 as a highly efficient reagent for one-pot N-alkylation of sulfonamides from alcohols: a rapid route to N-alkyl sulfonamides synthesis.

Authors:  Mohammad Navid Soltani Rad; Somayeh Behrouz
Journal:  Mol Divers       Date:  2013-08-14       Impact factor: 2.943

8.  Allylic amination and N-arylation-based domino reactions providing rapid three-component strategies to fused pyrroles with different substituted patterns.

Authors:  Bo Jiang; Ying Li; Man-Su Tu; Shu-Liang Wang; Shu-Jiang Tu; Guigen Li
Journal:  J Org Chem       Date:  2012-08-13       Impact factor: 4.354

9.  C(sp3)-H methylation enabled by peroxide photosensitization and Ni-mediated radical coupling.

Authors:  Aristidis Vasilopoulos; Shane W Krska; Shannon S Stahl
Journal:  Science       Date:  2021-04-23       Impact factor: 47.728

10.  Copper-catalyzed aerobic oxidative coupling: From ketone and diamine to pyrazine.

Authors:  Kun Wu; Zhiliang Huang; Xiaotian Qi; Yingzi Li; Guanghui Zhang; Chao Liu; Hong Yi; Lingkui Meng; Emilio E Bunel; Jeffrey T Miller; Chih-Wen Pao; Jyh-Fu Lee; Yu Lan; Aiwen Lei
Journal:  Sci Adv       Date:  2015-10-09       Impact factor: 14.136

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