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Literature DB >> 24740762

Chemoselective intermolecular α-arylation of amides.

Bo Peng¹, Danny Geerdink, Christophe Farès, Nuno Maulide.

Abstract

A new approach for the fully chemoselective α-arylation of amides is presented. By means of electrophilic amide activation, aryl groups can be regioselectively introduced α- to amides, even in the presence of esters and alkyl ketones. Mechanistic studies reveal key reaction intermediates and emphasize a remarkably subtle base effect in this transformation.

Entities: Chemical

Keywords: amides; arylation; chemoselectivity; keteniminium ions; sulfoxides

Year: 2014 PMID： 24740762 DOI： 10.1002/anie.201402229

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

26 in total

1. Direct Observation of Intermediates Involved in the Interruption of the Bischler-Napieralski Reaction.

Authors: Kolby L White; Marius Mewald; Mohammad Movassaghi
Journal: J Org Chem Date: 2015-07-22 Impact factor: 4.354

2. Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

Authors: Daniel Kaiser; Immo Klose; Rik Oost; James Neuhaus; Nuno Maulide
Journal: Chem Rev Date: 2019-06-25 Impact factor: 60.622

3. Mechanistic Pathways in Amide Activation: Flexible Synthesis of Oxazoles and Imidazoles.

Authors: Giovanni Di Mauro; Boris Maryasin; Daniel Kaiser; Saad Shaaban; Leticia González; Nuno Maulide
Journal: Org Lett Date: 2017-07-13 Impact factor: 6.005

4. The ketene-surrogate coupling: catalytic conversion of aryl iodides into aryl ketenes through ynol ethers.

Authors: Wenhan Zhang; Joseph M Ready
Journal: Angew Chem Int Ed Engl Date: 2014-06-27 Impact factor: 15.336

5. Uniting Amide Synthesis and Activation by P^III/P^V-Catalyzed Serial Condensation: Three-Component Assembly of 2-Amidopyridines.

Authors: Jeffrey M Lipshultz; Alexander T Radosevich
Journal: J Am Chem Soc Date: 2021-09-03 Impact factor: 16.383

Chemoselective intermolecular α-arylation of amides.

1. Direct Observation of Intermediates Involved in the Interruption of the Bischler-Napieralski Reaction.

2. Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

3. Mechanistic Pathways in Amide Activation: Flexible Synthesis of Oxazoles and Imidazoles.

4. The ketene-surrogate coupling: catalytic conversion of aryl iodides into aryl ketenes through ynol ethers.

5. Uniting Amide Synthesis and Activation by P^III/P^V-Catalyzed Serial Condensation: Three-Component Assembly of 2-Amidopyridines.

6. Sulfoxide-Directed Metal-Free ortho-Propargylation of Aromatics and Heteroaromatics.

7. Metal-Free C-H Alkyliminylation and Acylation of Alkenes with Secondary Amides.

8. Chemo- and Stereoselective Transition-Metal-Free Amination of Amides with Azides.

9. Mild Reductive Functionalization of Amides into N-Sulfonylformamidines.

10. A bioinspired and biocompatible ortho-sulfiliminyl phenol synthesis.