Literature DB >> 31961696

Nickel-Catalyzed Deaminative Acylation of Activated Aliphatic Amines with Aromatic Amides via C-N Bond Activation.

Chu-Guo Yu1, Yutaka Matsuo1,2.   

Abstract

Deaminative functionalization of aliphatic primary amines has great synthetic utility. Herein, we describe a Ni-catalyzed reductive deaminative cross-electrophile coupling reaction between Katritzky salts and aromatic amides. This work provides examples of the synthesis of various ketones from alkylpyridinium salts, including both primary and secondary alkylamines. Given its mild reaction conditions and high functional group tolerance, this cross-coupling strategy is expected to be useful for late-stage functionalization of complex compounds.

Entities:  

Year:  2020        PMID: 31961696     DOI: 10.1021/acs.orglett.9b04497

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


  7 in total

Review 1.  Recent Progress in Fragmentation of Katritzky Salts Enabling Formation of C-C, C-B, and C-S Bonds.

Authors:  Yuan Gao; Songwei Jiang; Nian-Dong Mao; Huan Xiang; Ji-Long Duan; Xiang-Yang Ye; Li-Wei Wang; Yang Ye; Tian Xie
Journal:  Top Curr Chem (Cham)       Date:  2022-05-19

2.  Dual Nickel/Photoredox-Catalyzed Deaminative Cross-Coupling of Sterically Hindered Primary Amines.

Authors:  Julia R Dorsheimer; Melissa A Ashley; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2021-11-12       Impact factor: 15.419

3.  Deaminative Reductive Methylation of Alkylpyridinium Salts.

Authors:  Olivia P Bercher; Shane Plunkett; Thomas E Mortimer; Mary P Watson
Journal:  Org Lett       Date:  2021-08-31       Impact factor: 6.072

4.  Nickel-Catalyzed Conversion of Amides to Carboxylic Acids.

Authors:  Rachel R Knapp; Ana S Bulger; Neil K Garg
Journal:  Org Lett       Date:  2020-03-25       Impact factor: 6.005

5.  Nickel-Catalyzed Synthesis of Dialkyl Ketones from the Coupling of N-Alkyl Pyridinium Salts with Activated Carboxylic Acids.

Authors:  Jiang Wang; Megan E Hoerrner; Mary P Watson; Daniel J Weix
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-05       Impact factor: 15.336

6.  Continuous-Flow Synthesis of Pyrylium Tetrafluoroborates: Application to Synthesis of Katritzky Salts and Photoinduced Cationic RAFT Polymerization.

Authors:  Carlo Sambiagio; Matteo Ferrari; Koen van Beurden; Nicola Della Ca'; Jack van Schijndel; Timothy Noël
Journal:  Org Lett       Date:  2021-03-02       Impact factor: 6.005

7.  Phosphite mediated asymmetric N to C migration for the synthesis of chiral heterocycles from primary amines.

Authors:  Soniya Rani; Soumya Ranjan Dash; Asish Bera; Md Nirshad Alam; Kumar Vanka; Pradip Maity
Journal:  Chem Sci       Date:  2021-05-28       Impact factor: 9.825

  7 in total

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