Literature DB >> 28514176

Transition-Metal-Free, Visible-Light-Enabled Decarboxylative Borylation of Aryl N-Hydroxyphthalimide Esters.

Lisa Candish1, Michael Teders1, Frank Glorius1.   

Abstract

Herein, we report a conceptually novel borylation reaction proceeding via a mild photoinduced decarboxylation of redox-activated aromatic carboxylic acids. This work constitutes the first application of cheap and easily prepared N-hydroxyphthalimide esters as aryl radical precursors and does not require the use of expensive transition metals or ligands. The reaction is operationally simple, scalable, and displays broad scope and functional group tolerance.

Entities:  

Year:  2017        PMID: 28514176     DOI: 10.1021/jacs.7b03127

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  30 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.  Light-Driven Intermolecular Charge Transfer Induced Reactivity of Ethynylbenziodoxol(on)e and Phenols.

Authors:  Bin Liu; Chern-Hooi Lim; Garret M Miyake
Journal:  J Am Chem Soc       Date:  2018-10-02       Impact factor: 15.419

3.  A Radical Approach to Anionic Chemistry: Synthesis of Ketones, Alcohols, and Amines.

Authors:  Shengyang Ni; Natalia M Padial; Cian Kingston; Julien C Vantourout; Daniel C Schmitt; Jacob T Edwards; Monika M Kruszyk; Rohan R Merchant; Pavel K Mykhailiuk; Brittany B Sanchez; Shouliang Yang; Matthew A Perry; Gary M Gallego; James J Mousseau; Michael R Collins; Robert J Cherney; Pavlo S Lebed; Jason S Chen; Tian Qin; Phil S Baran
Journal:  J Am Chem Soc       Date:  2019-04-16       Impact factor: 15.419

4.  Visible-Light-Promoted C-S Cross-Coupling via Intermolecular Charge Transfer.

Authors:  Bin Liu; Chern-Hooi Lim; Garret M Miyake
Journal:  J Am Chem Soc       Date:  2017-09-19       Impact factor: 15.419

5.  Hydroesterification and difunctionalization of olefins with N-hydroxyphthalimide esters.

Authors:  Lingying Leng; Joseph M Ready
Journal:  ACS Catal       Date:  2021-10-27       Impact factor: 13.700

6.  Direct Carbon Isotope Exchange through Decarboxylative Carboxylation.

Authors:  Cian Kingston; Michael A Wallace; Alban J Allentoff; Justine N deGruyter; Jason S Chen; Sharon X Gong; Samuel Bonacorsi; Phil S Baran
Journal:  J Am Chem Soc       Date:  2019-01-03       Impact factor: 15.419

7.  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

8.  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

9.  Evolution of a Synthetic Strategy for Complex Polypyrrole Alkaloids: Total Syntheses of Curvulamine and Curindolizine.

Authors:  Jun Xuan; Karl T Haelsig; Michael Sheremet; Paulo A Machicao; Thomas J Maimone
Journal:  J Am Chem Soc       Date:  2021-02-11       Impact factor: 15.419

10.  A visible-light mediated ring opening reaction of alkylidenecyclopropanes for the generation of homopropargyl radicals.

Authors:  Xiao-Yu Zhang; Chao Ning; Ben Mao; Yin Wei; Min Shi
Journal:  Chem Sci       Date:  2021-05-28       Impact factor: 9.825

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