Literature DB >> 29375927

Nickel/Photoredox-Catalyzed Amidation via Alkylsilicates and Isocyanates.

Shuai Zheng1, David N Primer1, Gary A Molander1.   

Abstract

A nickel/photoredox, dual-catalyzed amidation reaction between alkylsilicate reagents and alkyl/aryl isocyanates is reported. In contrast to the previously reported reductive coupling process, this protocol is characterized by mild reaction conditions and the absence of a stoichiometric reductant. A mechanistic hypothesis involving a nickel-isocyanate adduct is proposed based on literature precedent and further validation by experimental results.

Entities:  

Keywords:  alkylsilicates; amidation; isocyanates; nickel/photoredox dual catalysis; radicals

Year:  2017        PMID： 29375927      PMCID： PMC5784433          DOI： 10.1021/acscatal.7b02795

Source DB:  PubMed          Journal:  ACS Catal            Impact factor:   13.084


  34 in total

1.  Nickel-Catalyzed Reductive Amidation of Unactivated Alkyl Bromides.

Authors:  Eloisa Serrano; Ruben Martin
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-30       Impact factor: 15.336

Review 2.  Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

Authors:  Ranjan Jana; Tejas P Pathak; Matthew S Sigman
Journal:  Chem Rev       Date:  2011-02-14       Impact factor: 60.622

Review 3.  Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Authors:  Christopher K Prier; Danica A Rankic; David W C MacMillan
Journal:  Chem Rev       Date:  2013-03-19       Impact factor: 60.622

4.  Ni-catalyzed direct reductive amidation via C-O bond cleavage.

Authors:  Arkaitz Correa; Ruben Martin
Journal:  J Am Chem Soc       Date:  2014-05-07       Impact factor: 15.419

Review 5.  C-N bond forming cross-coupling reactions: an overview.

Authors:  Jitender Bariwal; Erik Van der Eycken
Journal:  Chem Soc Rev       Date:  2013-09-30       Impact factor: 54.564

6.  Nickel-Catalyzed Synthesis of Quinazolinediones.

Authors:  Gregory L Beutner; Yi Hsiao; Thomas Razler; Eric M Simmons; William Wertjes
Journal:  Org Lett       Date:  2017-02-13       Impact factor: 6.005

7.  Nonclassical Routes for Amide Bond Formation.

Authors:  Renata Marcia de Figueiredo; Jean-Simon Suppo; Jean-Marc Campagne
Journal:  Chem Rev       Date:  2016-09-22       Impact factor: 60.622

8.  Direct Conversion of Carboxylic Acids to Alkyl Ketones.

Authors:  Javad Amani; Gary A Molander
Journal:  Org Lett       Date:  2017-06-12       Impact factor: 6.005

9.  Phenol Derivatives as Coupling Partners with Alkylsilicates in Photoredox/Nickel Dual Catalysis.

Authors:  Niki R Patel; Gary A Molander
Journal:  J Org Chem       Date:  2016-06-03       Impact factor: 4.354

10.  Visible Light Photoredox Cross-Coupling of Acyl Chlorides with Potassium Alkoxymethyltrifluoroborates: Synthesis of α-Alkoxyketones.

Authors:  Javad Amani; Esmat Sodagar; Gary A Molander
Journal:  Org Lett       Date:  2016-02-01       Impact factor: 6.005
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  8 in total

1.  Synthesis of amino-diamondoid pharmacophores via photocatalytic C-H aminoalkylation.

Authors:  William K Weigel; Hoang T Dang; Hai-Bin Yang; David B C Martin
Journal:  Chem Commun (Camb)       Date:  2020-08-20       Impact factor: 6.222

Review 2.  Alkyl Carbon-Carbon Bond Formation by Nickel/Photoredox Cross-Coupling.

Authors:  John A Milligan; James P Phelan; Shorouk O Badir; Gary A Molander
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-27       Impact factor: 15.336

3.  Photoredox/Nickel-Catalyzed Single-Electron Tsuji-Trost Reaction: Development and Mechanistic Insights.

Authors:  Jennifer K Matsui; Álvaro Gutiérrez-Bonet; Madeline Rotella; Rauful Alam; Osvaldo Gutierrez; Gary A Molander
Journal:  Angew Chem Int Ed Engl       Date:  2018-11-07       Impact factor: 15.336

4.  Amide Synthesis by Nickel/Photoredox-Catalyzed Direct Carbamoylation of (Hetero)Aryl Bromides.

Authors:  Nurtalya Alandini; Luca Buzzetti; Gianfranco Favi; Tim Schulte; Lisa Candish; Karl D Collins; Paolo Melchiorre
Journal:  Angew Chem Int Ed Engl       Date:  2020-02-25       Impact factor: 15.336

5.  A chiral nickel DBFOX complex as a bifunctional catalyst for visible-light-promoted asymmetric photoredox reactions.

Authors:  Xiang Shen; Yanjun Li; Zhaorui Wen; Shi Cao; Xinyi Hou; Lei Gong
Journal:  Chem Sci       Date:  2018-04-27       Impact factor: 9.825

6.  Desulfonative photoredox alkylation of N-heteroaryl sulfones - an acid-free approach for substituted heteroarene synthesis.

Authors:  Zheng-Jun Wang; Shuai Zheng; Jennifer K Matsui; Zhipeng Lu; Gary A Molander
Journal:  Chem Sci       Date:  2019-03-14       Impact factor: 9.825

7.  Generation of Alkyl Radicals: From the Tyranny of Tin to the Photon Democracy.

Authors:  Stefano Crespi; Maurizio Fagnoni
Journal:  Chem Rev       Date:  2020-08-06       Impact factor: 60.622

Review 8.  Recent Advances in Visible-Light-Mediated Amide Synthesis.

Authors:  Bin Lu; Wen-Jing Xiao; Jia-Rong Chen
Journal:  Molecules       Date:  2022-01-14       Impact factor: 4.411
  8 in total

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