Literature DB >> 26991022

Nickel-Catalyzed Carboxylation of Benzylic C-N Bonds with CO2.

Toni Moragas1, Morgane Gaydou1, Ruben Martin2,3.   

Abstract

A user-friendly Ni-catalyzed reductive carboxylation of benzylic C-N bonds with CO2 is described. This procedure outperforms state-of-the-art techniques for the carboxylation of benzyl electrophiles by avoiding commonly observed parasitic pathways, such as homodimerization or β-hydride elimination, thus leading to new knowledge in cross-electrophile reactions.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−N activation; carboxylation; homogeneous catalysis; nickel; reductive coupling

Year:  2016        PMID： 26991022     DOI： 10.1002/anie.201600697

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


  20 in total

1.  Synthesis of β-Phenethylamines via Ni/Photoredox Cross-Electrophile Coupling of Aliphatic Aziridines and Aryl Iodides.

Authors:  Talia J Steiman; Junyi Liu; Amanuella Mengiste; Abigail G Doyle
Journal:  J Am Chem Soc       Date:  2020-04-06       Impact factor: 15.419

2.  Activation of diverse carbon-heteroatom and carbon-carbon bonds via palladium(II)-catalysed β-X elimination.

Authors:  Van T Tran; John A Gurak; Kin S Yang; Keary M Engle
Journal:  Nat Chem       Date:  2018-08-20       Impact factor: 24.427

3.  Vinylation of Benzylic Amines via C-N Bond Functionalization of Benzylic Pyridinium Salts.

Authors:  Weiye Guan; Jennie Liao; Mary P Watson
Journal:  Synthesis (Stuttg)       Date:  2018-06-08       Impact factor: 3.157

4.  Harnessing Alkyl Amines as Electrophiles for Nickel-Catalyzed Cross Couplings via C-N Bond Activation.

Authors:  Corey H Basch; Jennie Liao; Jianyu Xu; Jacob J Piane; Mary P Watson
Journal:  J Am Chem Soc       Date:  2017-04-05       Impact factor: 15.419

5.  Development of an Improved System for the Carboxylation of Aryl Halides through Mechanistic Studies.

Authors:  David J Charboneau; Gary W Brudvig; Nilay Hazari; Hannah M C Lant; Andrew K Saydjari
Journal:  ACS Catal       Date:  2019-03-14       Impact factor: 13.084

6.  Deaminative Reductive Cross-Electrophile Couplings of Alkylpyridinium Salts and Aryl Bromides.

Authors:  Jennie Liao; Corey H Basch; Megan E Hoerrner; Michael R Talley; Brian P Boscoe; Joseph W Tucker; Michelle R Garnsey; Mary P Watson
Journal:  Org Lett       Date:  2019-03-27       Impact factor: 6.005

7.  Dissection of Alkylpyridinium Structures to Understand Deamination Reactions.

Authors:  Sergei Tcyrulnikov; Qiuqi Cai; J Cameron Twitty; Jianyu Xu; Abderrahman Atifi; Olivia P Bercher; Glenn P A Yap; Joel Rosenthal; Mary P Watson; Marisa C Kozlowski
Journal:  ACS Catal       Date:  2021-06-28       Impact factor: 13.700

8.  Harnessing Alkylpyridinium Salts as Electrophiles in Deaminative Alkyl-Alkyl Cross-Couplings.

Authors:  Shane Plunkett; Corey H Basch; Samantha O Santana; Mary P Watson
Journal:  J Am Chem Soc       Date:  2019-01-30       Impact factor: 15.419

9.  Transforming Benzylic Amines into Diarylmethanes: Cross-Couplings of Benzylic Pyridinium Salts via C-N Bond Activation.

Authors:  Jennie Liao; Weiye Guan; Brian P Boscoe; Joseph W Tucker; John W Tomlin; Michelle R Garnsey; Mary P Watson
Journal:  Org Lett       Date:  2018-05-10       Impact factor: 6.005

10.  Nickel-Catalyzed, Stereospecific C-C and C-B Cross-Couplings via C-N and C-O Bond Activation.

Authors:  Jianyu Xu; Olivia P Bercher; Michael R Talley; Mary P Watson
Journal:  ACS Catal       Date:  2021-01-19       Impact factor: 13.084
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