Literature DB >> 27282517

Combination of organotrifluoroborates with photoredox catalysis marking a new phase in organic radical chemistry.

Takashi Koike1, Munetaka Akita.   

Abstract

Combination of organotrifluoroborates and visible-light-driven photoredox catalysis, both of which have attracted the attention of synthetic chemists, marks a new phase in the field of organic radical chemistry. We have developed photoredox-catalyzed radical reactions with organotrifluoroborates, which turn out to serve not only as a source of organic radicals but also as radical acceptors. The first part of this Perspective deals with the generation of organic radicals from organotrifluoroborates, and the latter part describes addition of the CF3 radical to alkenyltrifluoroborates. The good chemistry between organoborates and photoredox catalysis and its future will be discussed.

Entities:  

Year:  2016        PMID: 27282517     DOI: 10.1039/c6ob00996d

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  8 in total

1.  Photoredox-Catalyzed Multicomponent Petasis Reaction with Alkyltrifluoroborates.

Authors:  Jun Yi; Shorouk O Badir; Rauful Alam; Gary A Molander
Journal:  Org Lett       Date:  2019-05-30       Impact factor: 6.005

2.  Photoredox-Catalyzed Oxidation of Anions for the Atom-Economical Hydro-, Amido-, and Dialkylation of Alkenes.

Authors:  Katherine C Forbes; Anne Marie Crooke; Yuri Lee; Masamu Kawada; Kian M Shamskhou; Rachel A Zhang; Jeffrey S Cannon
Journal:  J Org Chem       Date:  2022-02-08       Impact factor: 4.354

3.  Advancements in Visible-Light-Enabled Radical C(sp)2-H Alkylation of (Hetero)arenes.

Authors:  Alexandra C Sun; Rory C McAtee; Edward J McClain; Corey R J Stephenson
Journal:  Synthesis (Stuttg)       Date:  2019-01-25       Impact factor: 2.969

4.  Construction of Complex Cyclobutane Building Blocks by Photosensitized [2 + 2] Cycloaddition of Vinyl Boronate Esters.

Authors:  Spencer O Scholz; Jesse B Kidd; Luca Capaldo; Niecia E Flikweert; Rowan M Littlefield; Tehshik P Yoon
Journal:  Org Lett       Date:  2021-04-12       Impact factor: 6.005

5.  Photoredox-mediated Minisci C-H alkylation of N-heteroarenes using boronic acids and hypervalent iodine.

Authors:  Guo-Xing Li; Christian A Morales-Rivera; Yaxin Wang; Fang Gao; Gang He; Peng Liu; Gong Chen
Journal:  Chem Sci       Date:  2016-07-12       Impact factor: 9.825

6.  Photo-induced trifunctionalization of bromostyrenes via remote radical migration reactions of tetracoordinate boron species.

Authors:  Chaokun Li; Shangteng Liao; Shanglin Chen; Nan Chen; Feng Zhang; Kai Yang; Qiuling Song
Journal:  Nat Commun       Date:  2022-04-04       Impact factor: 14.919

7.  A Lewis Base Catalysis Approach for the Photoredox Activation of Boronic Acids and Esters.

Authors:  Fabio Lima; Upendra K Sharma; Lars Grunenberg; Debasmita Saha; Sandra Johannsen; Joerg Sedelmeier; Erik V Van der Eycken; Steven V Ley
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-24       Impact factor: 15.336

8.  Photoredox-Catalyzed Cyclobutane Synthesis by a Deboronative Radical Addition-Polar Cyclization Cascade.

Authors:  Chao Shu; Adam Noble; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-15       Impact factor: 15.336

  8 in total

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