Literature DB >> 28474531

Decarboxylative Borylation of Aliphatic Esters under Visible-Light Photoredox Conditions.

Dawei Hu1, Linghua Wang1, Pengfei Li1.   

Abstract

The conventional methods for preparing alkyl boronates often necessitate anhydrous and demanding reaction conditions. Herein, a new, operationally simple decarboxylative borylation reaction of readily available aliphatic acid derivatives under additive-free visible-light photoredox conditions in nonanhydrous solvents has been described. Primary and secondary alkyl boronates or tetrafluoroborates with various functional groups were prepared accordingly. A catalytic cycle involving alkyl radical reaction with base-activated diboron species has been proposed.

Entities:  

Year:  2017        PMID: 28474531     DOI: 10.1021/acs.orglett.7b01181

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


  19 in total

1.  Decarboxylative Alkynylation.

Authors:  Joel M Smith; Tian Qin; Rohan R Merchant; Jacob T Edwards; Lara R Malins; Zhiqing Liu; Guanda Che; Zichao Shen; Scott A Shaw; Martin D Eastgate; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-01       Impact factor: 15.336

2.  Electrochemical borylation of carboxylic acids.

Authors:  Lisa M Barton; Longrui Chen; Donna G Blackmond; Phil S Baran
Journal:  Proc Natl Acad Sci U S A       Date:  2021-08-24       Impact factor: 11.205

3.  Exploiting the sp2 character of bicyclo[1.1.1]pentyl radicals in the transition-metal-free multi-component difunctionalization of [1.1.1]propellane.

Authors:  Weizhe Dong; Expédite Yen-Pon; Longbo Li; Ayan Bhattacharjee; Anais Jolit; Gary A Molander
Journal:  Nat Chem       Date:  2022-07-21       Impact factor: 24.274

4.  Umpolung AlaB Reagents for the Synthesis of Non-Proteogenic Amino Acids, Peptides and Proteins.

Authors:  Feng Zhu; Eric Miller; Wyatt C Powell; Kelly Johnson; Alexander Beggs; Garrett E Evenson; Maciej A Walczak
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-23       Impact factor: 16.823

5.  Organoboron chemistry comes to light: recent advances in photoinduced synthetic approaches to organoboron compounds.

Authors:  Viet D Nguyen; Vu T Nguyen; Shengfei Jin; Hang T Dang; Oleg V Larionov
Journal:  Tetrahedron       Date:  2018-12-24       Impact factor: 2.457

6.  Visible Light-Induced Borylation of C-O, C-N, and C-X Bonds.

Authors:  Shengfei Jin; Hang T Dang; Graham C Haug; Ru He; Viet D Nguyen; Vu T Nguyen; Hadi D Arman; Kirk S Schanze; Oleg V Larionov
Journal:  J Am Chem Soc       Date:  2020-01-10       Impact factor: 15.419

7.  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

8.  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

9.  Transition Metal-Free 1,2-Carboboration of Unactivated Alkenes.

Authors:  Ying Cheng; Christian Mück-Lichtenfeld; Armido Studer
Journal:  J Am Chem Soc       Date:  2018-05-15       Impact factor: 15.419

10.  Facile synthesis of α-aminoboronic acids from amines and potassium acyltrifluoroborates (KATs) via trifluoroborate-iminiums (TIMs).

Authors:  Tomoya Shiro; Anne Schuhmacher; Moritz K Jackl; Jeffrey W Bode
Journal:  Chem Sci       Date:  2018-05-16       Impact factor: 9.825

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