Literature DB >> 33629454

Recent Advances in Photoredox-Mediated Radical Conjugate Addition Reactions: An Expanding Toolkit for the Giese Reaction.

Anastasia L Gant Kanegusuku1, Jennifer L Roizen1.   

Abstract

Photomediated Giese reactions are at the forefront of radical chemistry, much like the classical tin-mediated Giese reactions were nearly forty years ago. With the global recognition of organometallic photocatalysts for the mild and tunable generation of carbon-centered radicals, chemists have developed a torrent of strategies to form previously inaccessible radical intermediates that are capable of engaging in intermolecular conjugate addition reactions. This Review summarizes advances in photoredox-mediated Giese reactions since 2013, with a focus on the breadth of methods that provide access to crucial carbon-centered radical intermediates that can engage in radical conjugate addition processes.
© 2021 Wiley-VCH GmbH.

Entities:  

Keywords:  Giese reaction; photocatalysis; photoredox catalysis; radical Michael addition; radical conjugate addition

Mesh:

Substances:

Year:  2021        PMID: 33629454      PMCID: PMC8382814          DOI: 10.1002/anie.202016666

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   16.823


  171 in total

1.  Photochemical generation of radicals from alkyl electrophiles using a nucleophilic organic catalyst.

Authors:  Bertrand Schweitzer-Chaput; Matthew A Horwitz; Eduardo de Pedro Beato; Paolo Melchiorre
Journal:  Nat Chem       Date:  2018-12-03       Impact factor: 24.427

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Journal:  Helv Chim Acta       Date:  1949       Impact factor: 2.164

3.  Factors Controlling the Addition of Carbon-Centered Radicals to Alkenes-An Experimental and Theoretical Perspective.

Authors:  Hanns Fischer; Leo Radom
Journal:  Angew Chem Int Ed Engl       Date:  2001-04-17       Impact factor: 15.336

4.  Radical cation Diels-Alder cycloadditions by visible light photocatalysis.

Authors:  Shishi Lin; Michael A Ischay; Charles G Fry; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2011-11-11       Impact factor: 15.419

5.  Visible-light-mediated utilization of α-aminoalkyl radicals: addition to electron-deficient alkenes using photoredox catalysts.

Authors:  Yoshihiro Miyake; Kazunari Nakajima; Yoshiaki Nishibayashi
Journal:  J Am Chem Soc       Date:  2012-02-08       Impact factor: 15.419

6.  Sn-free Ni-catalyzed reductive coupling of glycosyl bromides with activated alkenes.

Authors:  Hegui Gong; R Stephen Andrews; Joseph L Zuccarello; Stephen J Lee; Michel R Gagné
Journal:  Org Lett       Date:  2009-02-19       Impact factor: 6.005

7.  Advances in Photocatalysis: A Microreview of Visible Light Mediated Ruthenium and Iridium Catalyzed Organic Transformations.

Authors:  Jon I Day; Kip Teegardin; Jimmie Weaver; John Chan
Journal:  Org Process Res Dev       Date:  2016-06-28       Impact factor: 3.317

8.  Oxalates as Activating Groups for Alcohols in Visible Light Photoredox Catalysis: Formation of Quaternary Centers by Redox-Neutral Fragment Coupling.

Authors:  Christopher C Nawrat; Christopher R Jamison; Yuriy Slutskyy; David W C MacMillan; Larry E Overman
Journal:  J Am Chem Soc       Date:  2015-08-31       Impact factor: 15.419

9.  Engaging unactivated alkyl, alkenyl and aryl iodides in visible-light-mediated free radical reactions.

Authors:  John D Nguyen; Erica M D'Amato; Jagan M R Narayanam; Corey R J Stephenson
Journal:  Nat Chem       Date:  2012-10       Impact factor: 24.427

10.  Free Radical Chemistry Enabled by Visible Light-Induced Electron Transfer.

Authors:  Daryl Staveness; Irene Bosque; Corey R J Stephenson
Journal:  Acc Chem Res       Date:  2016-08-16       Impact factor: 22.384

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  8 in total

Review 1.  Strategies to Generate Nitrogen-centered Radicals That May Rely on Photoredox Catalysis: Development in Reaction Methodology and Applications in Organic Synthesis.

Authors:  Kitae Kwon; R Thomas Simons; Meganathan Nandakumar; Jennifer L Roizen
Journal:  Chem Rev       Date:  2021-10-08       Impact factor: 60.622

2.  Radical C(sp3)-H functionalization and cross-coupling reactions.

Authors:  Dung L Golden; Sung-Eun Suh; Shannon S Stahl
Journal:  Nat Rev Chem       Date:  2022-05-17       Impact factor: 34.571

3.  Alcohols as Alkylating Agents: Photoredox-Catalyzed Conjugate Alkylation via In Situ Deoxygenation.

Authors:  Johnny Z Wang; Holt A Sakai; David W C MacMillan
Journal:  Angew Chem Int Ed Engl       Date:  2022-07-19       Impact factor: 16.823

Review 4.  Photocatalytic C(sp3) radical generation via C-H, C-C, and C-X bond cleavage.

Authors:  Chia-Yu Huang; Jianbin Li; Chao-Jun Li
Journal:  Chem Sci       Date:  2022-04-18       Impact factor: 9.969

5.  Photocatalytic Late-Stage Functionalization of Sulfonamides via Sulfonyl Radical Intermediates.

Authors:  Michael J Tilby; Damien F Dewez; Loïc R E Pantaine; Adrian Hall; Carolina Martínez-Lamenca; Michael C Willis
Journal:  ACS Catal       Date:  2022-05-06       Impact factor: 13.700

6.  Access to chiral β-sulfonyl carbonyl compounds via photoinduced organocatalytic asymmetric radical sulfonylation with sulfur dioxide.

Authors:  Fu-Sheng He; Chun Zhang; Minghui Jiang; Lujun Lou; Jie Wu; Shengqing Ye
Journal:  Chem Sci       Date:  2022-07-08       Impact factor: 9.969

7.  Facile Conversion of α-Amino Acids into α-Amino Phosphonates by Decarboxylative Phosphorylation using Visible-Light Photocatalysis.

Authors:  Dominik Reich; Adam Noble; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2022-08-04       Impact factor: 16.823

8.  A General Organocatalytic System for Electron Donor-Acceptor Complex Photoactivation and Its Use in Radical Processes.

Authors:  Eduardo de Pedro Beato; Davide Spinnato; Wei Zhou; Paolo Melchiorre
Journal:  J Am Chem Soc       Date:  2021-07-28       Impact factor: 15.419

  8 in total

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