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Literature DB >> 23272978

Copper-catalyzed direct arylation of cyclic enamides using diaryliodonium salts.

Nicolas Gigant¹, Laëtitia Chausset-Boissarie, Marie-Charlotte Belhomme, Thomas Poisson, Xavier Pannecoucke, Isabelle Gillaizeau.

Abstract

A convenient method for the copper(II)-catalyzed direct arylation of cyclic and nonaromatic enamides using diaryliodonium salts has been developed. The reaction demonstrates large functional group tolerance, good yields, and total regioselectivity with a C(3)-functionalization. The synthetic potential of this coupling was explored by using a range of readily accessible diaryliodonium salts and enamides.

Entities: Chemical

Year: 2012 PMID： 23272978 DOI： 10.1021/ol303400s

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

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Cited

6 in total

1. Direct access to functionalized azepanes by cross-coupling with α-halo eneformamides.

Authors: Timothy K Beng; Sidney M Wilkerson-Hill; Richmond Sarpong
Journal: Org Lett Date: 2014-01-23 Impact factor: 6.005

2. Photoredox-catalyzed stereoselective alkylation of enamides with N-hydroxyphthalimide esters via decarboxylative cross-coupling reactions.

Authors: Jing-Yu Guo; Ze-Yu Zhang; Ting Guan; Lei-Wen Mao; Qian Ban; Kai Zhao; Teck-Peng Loh
Journal: Chem Sci Date: 2019-08-05 Impact factor: 9.825

3. A general synthesis of azetidines by copper-catalysed photoinduced anti-Baldwin radical cyclization of ynamides.

Authors: Clément Jacob; Hajar Baguia; Amaury Dubart; Samuel Oger; Pierre Thilmany; Jérôme Beaudelot; Christopher Deldaele; Stefano Peruško; Yohann Landrain; Bastien Michelet; Samuel Neale; Eugénie Romero; Cécile Moucheron; Veronique Van Speybroeck; Cédric Theunissen; Gwilherm Evano
Journal: Nat Commun Date: 2022-01-28 Impact factor: 17.694

Copper-catalyzed direct arylation of cyclic enamides using diaryliodonium salts.

1. Direct access to functionalized azepanes by cross-coupling with α-halo eneformamides.

2. Photoredox-catalyzed stereoselective alkylation of enamides with N-hydroxyphthalimide esters via decarboxylative cross-coupling reactions.

3. A general synthesis of azetidines by copper-catalysed photoinduced anti-Baldwin radical cyclization of ynamides.

4. Copper-catalyzed transformation of alkyl nitriles to N-arylacetamide using diaryliodonium salts.

5. Direct C-H functionalization of difluoroboron dipyrromethenes (BODIPYs) at β-position by iodonium salts.

6. Direct Synthesis of Enamides via Electrophilic Activation of Amides.