Literature DB >> 19751053

Inter- and intramolecular addition reactions of electron-deficient alkenes with alkyl radicals, generated by SET-photochemical decarboxylation of carboxylic acids, serve as a mild and efficient method for the preparation of gamma-amino acids and macrocyclic lactones.

Yasuharu Yoshimi1, Miho Masuda, Tomoyuki Mizunashi, Keisuke Nishikawa, Kousuke Maeda, Nobumasa Koshida, Tatsuya Itou, Toshio Morita, Minoru Hatanaka.   

Abstract

Inter- and intramolecular additions of alkyl radicals, generated by SET photochemical decarboxylation reactions of free carboxylic acids, to electron-deficient alkenes take place under mild conditions as part of efficient routes for the formation of N-Boc gamma-amino acids and macrocyclic lactones.

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Year:  2009        PMID: 19751053     DOI: 10.1021/ol9019277

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


  8 in total

1.  Hydrodecarboxylation of Carboxylic and Malonic Acid Derivatives via Organic Photoredox Catalysis: Substrate Scope and Mechanistic Insight.

Authors:  Jeremy D Griffin; Mary A Zeller; David A Nicewicz
Journal:  J Am Chem Soc       Date:  2015-08-28       Impact factor: 15.419

2.  Photocatalytic Aminodecarboxylation of Carboxylic Acids.

Authors:  Simon B Lang; Kaitie C Cartwright; Richard S Welter; Theresa M Locascio; Jon A Tunge
Journal:  European J Org Chem       Date:  2016-06-19

Review 3.  Recent Advances in Photoredox-Mediated Radical Conjugate Addition Reactions: An Expanding Toolkit for the Giese Reaction.

Authors:  Anastasia L Gant Kanegusuku; Jennifer L Roizen
Journal:  Angew Chem Int Ed Engl       Date:  2021-07-21       Impact factor: 16.823

4.  Influence of solvent, electron acceptors and arenes on photochemical decarboxylation of free carboxylic acids via single electron transfer (SET).

Authors:  Yasuharu Yoshimi; Shota Hayashi; Keisuke Nishikawa; Yoshiki Haga; Kousuke Maeda; Toshio Morita; Tatsuya Itou; Yutaka Okada; Nobuyuki Ichinose; Minoru Hatanaka
Journal:  Molecules       Date:  2010-04-12       Impact factor: 4.411

5.  Picosecond to millisecond tracking of a photocatalytic decarboxylation reaction provides direct mechanistic insights.

Authors:  Aditi Bhattacherjee; Mahima Sneha; Luke Lewis-Borrell; Omri Tau; Ian P Clark; Andrew J Orr-Ewing
Journal:  Nat Commun       Date:  2019-11-13       Impact factor: 14.919

6.  Photoinduced Electron Transfer-Promoted Reactions Using Exciplex-Type Organic Photoredox Catalyst Directly Linking Donor and Acceptor Arenes.

Authors:  Mugen Yamawaki; Akiko Asano; Toshiki Furutani; Yuki Izumi; Yosuke Tanaka; Kazuyuki Osaka; Toshio Morita; Yasuharu Yoshimi
Journal:  Molecules       Date:  2019-12-05       Impact factor: 4.411

7.  Decarboxylative allylation of amino alkanoic acids and esters via dual catalysis.

Authors:  Simon B Lang; Kathryn M O'Nele; Jon A Tunge
Journal:  J Am Chem Soc       Date:  2014-09-22       Impact factor: 15.419

8.  Carboxylic acids as a traceless activation group for conjugate additions: a three-step synthesis of (±)-pregabalin.

Authors:  Lingling Chu; Chisa Ohta; Zhiwei Zuo; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2014-07-28       Impact factor: 15.419

  8 in total

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