Literature DB >> 26366608

Decarboxylative 1,4-Addition of α-Oxocarboxylic Acids with Michael Acceptors Enabled by Photoredox Catalysis.

Guang-Zu Wang1, Rui Shang1, Wan-Min Cheng1, Yao Fu1.   

Abstract

Enabled by iridium photoredox catalysis, 2-oxo-2-(hetero)arylacetic acids were decarboxylatively added to various Michael acceptors including α,β-unsaturated ester, ketone, amide, aldehyde, nitrile, and sulfone at room temperature. The reaction presents a new type of acyl Michael addition using stable and easily accessible carboxylic acid to formally generate acyl anion through photoredox-catalyzed radical decarboxylation.

Entities:  

Year:  2015        PMID： 26366608     DOI： 10.1021/acs.orglett.5b02392

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


  8 in total

1.  α-Silyl Amides: Effective Bifunctional Lynchpins for Type I Anion Relay Chemistry.

Authors:  Thomas D Montgomery; Amos B Smith
Journal:  Org Lett       Date:  2017-11-09       Impact factor: 6.005

2.  Three-component carboacylation of alkenes via cooperative nickelaphotoredox catalysis.

Authors:  Dingyi Wang; Lutz Ackermann
Journal:  Chem Sci       Date:  2022-05-30       Impact factor: 9.969

3.  Acyl Radical Chemistry via Visible-Light Photoredox Catalysis.

Authors:  Arghya Banerjee; Zhen Lei; Ming-Yu Ngai
Journal:  Synthesis (Stuttg)       Date:  2018-12-12       Impact factor: 3.157

4.  A Sequential Umpolung/Enzymatic Dynamic Kinetic Resolution Strategy for the Synthesis of γ-Lactones.

Authors:  Mark A Maskeri; Malte L Schrader; Karl A Scheidt
Journal:  Chemistry       Date:  2020-04-24       Impact factor: 5.236

5.  Stereocontrolled Synthesis of 1,4-Dicarbonyl Compounds by Photochemical Organocatalytic Acyl Radical Addition to Enals.

Authors:  Giulio Goti; Bartosz Bieszczad; Alberto Vega-Peñaloza; Paolo Melchiorre
Journal:  Angew Chem Int Ed Engl       Date:  2018-12-20       Impact factor: 15.336

6.  Diverse synthesis of C2-linked functionalized molecules via molecular glue strategy with acetylene.

Authors:  Bo Yang; Shaodong Lu; Yongdong Wang; Shifa Zhu
Journal:  Nat Commun       Date:  2022-04-06       Impact factor: 17.694

7.  Photocatalyzed Functionalization of Alkenoic Acids in 3D-Printed Reactors.

Authors:  Alexandra Jorea; Davide Ravelli; Rodrigo M Romarowski; Stefania Marconi; Ferdinando Auricchio; Maurizio Fagnoni
Journal:  ChemSusChem       Date:  2022-07-08       Impact factor: 9.140

8.  Photochemical generation of acyl and carbamoyl radicals using a nucleophilic organic catalyst: applications and mechanism thereof.

Authors:  Eduardo de Pedro Beato; Daniele Mazzarella; Matteo Balletti; Paolo Melchiorre
Journal:  Chem Sci       Date:  2020-06-04       Impact factor: 9.825
  8 in total

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