Literature DB >> 34350919

Evolution towards green radical generation in total synthesis.

Matthew S Galliher1, Bec J Roldan1, Corey R J Stephenson1.   

Abstract

The use of radicals as intermediates in total synthesis has evolved since their initial use in the latter half of the twentieth century. Radical generation from metal hydride methodologies has shifted to "greener" techniques including catalytic metal-mediated systems, electrochemical and photoredox-mediated processes. This review will focus on these classical and contemporary methods for radical generation and their applications in recent total syntheses.

Entities:  

Year:  2021        PMID: 34350919      PMCID: PMC9074136          DOI: 10.1039/d1cs00411e

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   60.615


  42 in total

1.  Generation of Dithianyl and Dioxolanyl Radicals Using Photoredox Catalysis: Application in the Total Synthesis of the Danshenspiroketallactones via Radical Relay Chemistry.

Authors:  Yifan Deng; Minh D Nguyen; Yike Zou; K N Houk; Amos B Smith
Journal:  Org Lett       Date:  2019-02-26       Impact factor: 6.005

2.  Electrochemical Dimerization of Phenylpropenoids and the Surprising Antioxidant Activity of the Resultant Quinone Methide Dimers.

Authors:  Kevin J Romero; Matthew S Galliher; Mark A R Raycroft; Jean-Philippe R Chauvin; Irene Bosque; Derek A Pratt; Corey R J Stephenson
Journal:  Angew Chem Int Ed Engl       Date:  2018-11-26       Impact factor: 15.336

3.  Understanding Initiation with Triethylboron and Oxygen: The Differences between Low-Oxygen and High-Oxygen Regimes.

Authors:  Dennis P Curran; Timothy R McFadden
Journal:  J Am Chem Soc       Date:  2016-06-14       Impact factor: 15.419

4.  Total Synthesis of (-)-Batrachotoxinin A: A Local-Desymmetrization Approach.

Authors:  Yinliang Guo; Zhixian Guo; Jia-Tian Lu; Runting Fang; Si-Cong Chen; Tuoping Luo
Journal:  J Am Chem Soc       Date:  2020-02-14       Impact factor: 15.419

5.  Total Synthesis of 1-Hydroxytaxinine.

Authors:  Yusuke Imamura; Shun Yoshioka; Masanori Nagatomo; Masayuki Inoue
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-25       Impact factor: 15.336

6.  A scalable biomimetic synthesis of resveratrol dimers and systematic evaluation of their antioxidant activities.

Authors:  Bryan S Matsuura; Mitchell H Keylor; Bo Li; YuXuan Lin; Shelby Allison; Derek A Pratt; Corey R J Stephenson
Journal:  Angew Chem Int Ed Engl       Date:  2015-02-04       Impact factor: 15.336

7.  Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins.

Authors:  Steven W M Crossley; Carla Obradors; Ruben M Martinez; Ryan A Shenvi
Journal:  Chem Rev       Date:  2016-07-27       Impact factor: 60.622

8.  Thirty Years of (TMS)3SiH: A Milestone in Radical-Based Synthetic Chemistry.

Authors:  Chryssostomos Chatgilialoglu; Carla Ferreri; Yannick Landais; Vitaliy I Timokhin
Journal:  Chem Rev       Date:  2018-06-25       Impact factor: 60.622

9.  Radicals in natural product synthesis.

Authors:  Kevin J Romero; Matthew S Galliher; Derek A Pratt; Corey R J Stephenson
Journal:  Chem Soc Rev       Date:  2018-10-29       Impact factor: 54.564

10.  Et3B-mediated two- and three-component coupling reactions via radical decarbonylation of α-alkoxyacyl tellurides: single-step construction of densely oxygenated carboskeletons.

Authors:  Masanori Nagatomo; Daigo Kamimura; Yuki Matsui; Keisuke Masuda; Masayuki Inoue
Journal:  Chem Sci       Date:  2015-03-06       Impact factor: 9.825

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  3 in total

1.  Visible-light-promoted and chlorophyll-catalyzed aerobic desulfurization of thioamides to amides.

Authors:  Zihui Yang; Haoyi Zhou; Lin Wang; Jingxuan Zhang; Hongqi Xie; Yisong Liu; Jianguo Zeng; Pi Cheng
Journal:  RSC Adv       Date:  2022-06-09       Impact factor: 4.036

2.  Photoinduced metal-free borylation of aryl halides catalysed by an in situ formed donor-acceptor complex.

Authors:  Manhong Li; Siqi Liu; Haoshi Bao; Qini Li; Yi-Hui Deng; Tian-Yu Sun; Leifeng Wang
Journal:  Chem Sci       Date:  2022-04-04       Impact factor: 9.969

3.  Direct C-H Trifluoromethylation of (Hetero)Arenes in Water Enabled by Organic Photoredox-Active Amphiphilic Nanoparticles.

Authors:  Fabian Eisenreich; Anja R A Palmans
Journal:  Chemistry       Date:  2022-07-28       Impact factor: 5.020

  3 in total

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