Literature DB >> 28918623

Intermolecular Radical Addition to Carbonyls Enabled by Visible Light Photoredox Initiated Hole Catalysis.

Lena Pitzer1, Frederik Sandfort1, Felix Strieth-Kalthoff1, Frank Glorius1.   

Abstract

Herein, we present a novel strategy for the utilization of simple carbonyl compounds, aldehydes and ketones, as intermolecular radical acceptors. The reaction is enabled by visible light photoredox initiated hole catalysis and the in situ Brønsted acid activation of the carbonyl compound. This regioselective alkyl radical addition reaction does not require metals, ligands or additives and proceeds with a high degree of atom economy under mild conditions. The proposed mechanism is supported by both experimental and theoretical studies.

Entities:  

Year:  2017        PMID: 28918623     DOI: 10.1021/jacs.7b08086

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


  7 in total

1.  Direct Synthesis of Secondary Benzylic Alcohols Enabled by Photoredox/Ni Dual-Catalyzed Cross-Coupling.

Authors:  Rauful Alam; Gary A Molander
Journal:  J Org Chem       Date:  2017-11-27       Impact factor: 4.354

2.  Branch-Selective Addition of Unactivated Olefins into Imines and Aldehydes.

Authors:  Jeishla L M Matos; Suhelen Vásquez-Céspedes; Jieyu Gu; Takuya Oguma; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2018-11-29       Impact factor: 15.419

3.  Organocatalytic reductive coupling of aldehydes with 1,1-diarylethylenes using an in situ generated pyridine-boryl radical.

Authors:  Jia Cao; Guoqiang Wang; Liuzhou Gao; Xu Cheng; Shuhua Li
Journal:  Chem Sci       Date:  2018-02-28       Impact factor: 9.825

4.  Perfluoroalkylative pyridylation of alkenes via 4-cyanopyridine-boryl radicals.

Authors:  Jia Cao; Guoqiang Wang; Liuzhou Gao; Hui Chen; Xueting Liu; Xu Cheng; Shuhua Li
Journal:  Chem Sci       Date:  2019-01-16       Impact factor: 9.825

5.  Photocatalytic carbanion generation - benzylation of aliphatic aldehydes to secondary alcohols.

Authors:  Karsten Donabauer; Mitasree Maity; Anna Lucia Berger; Gregory S Huff; Stefano Crespi; Burkhard König
Journal:  Chem Sci       Date:  2019-04-16       Impact factor: 9.825

Review 6.  Reductive radical-polar crossover: traditional electrophiles in modern radical reactions.

Authors:  Lena Pitzer; J Luca Schwarz; Frank Glorius
Journal:  Chem Sci       Date:  2019-08-16       Impact factor: 9.825

7.  Light-enabled metal-free pinacol coupling by hydrazine.

Authors:  Zihang Qiu; Hanh D M Pham; Jianbin Li; Chen-Chen Li; Durbis J Castillo-Pazos; Rustam Z Khaliullin; Chao-Jun Li
Journal:  Chem Sci       Date:  2019-10-11       Impact factor: 9.825

  7 in total

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