Visible light induced Barton decarboxylation free of radical initiators

Wang Jiaxin; Fu Mingchen

doi:10.3969/j.issn.0253-2778.2020.11.004

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Open Access JUSTC Research Article

Visible light induced Barton decarboxylation free of radical initiators

Wang Jiaxin,
Fu Mingchen^,

Department of Chemistry, University of Science and Technology of China, Hefei 230026, China

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https://doi.org/10.3969/j.issn.0253-2778.2020.11.004

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Author Bio:
Wang Jiaxin is currently a Master student in the Lab of Anhui Province Key Laboratory of Biomass Clean Energy under the supervision of Associate Prof. Shi Jing at University of Science and Technology of China. Her current research mainly focuses on visible light driven radical synthetic chemistry.
Corresponding author: Fu Mingchen (corresponding author) received his Ph.D. degree in Organic Chemistry from University of Science and Technology of China (USTC). He is currently an associate researcher at USTC. His research interests include photochemistry in organic synthesis and carbonylation reaction using formic acid as the carbon source. E-mail: fumingchen@ustc.edu.cn
Received Date: 09 November 2020
Rev Recd Date: 23 November 2020
Publish Date: 30 November 2020

Abstract Full text PDF

Abstract

Abstract

Herein, a novel protocol for visible light induced decarboxylation was reported. The method avoids the addition of radical initiators. A series of primary, secondary, and tertiary redox-active esters underwent decarboxylation efficiently, as well as amino acid and peptide derivatives. Many natural products and drug molecules containing carboxyl groups can also be transformed well. The method has mild reaction conditions, wide substrate scope, satisfactory functional group compatibility with good to excellent yields. The preliminary mechanism studies suggested that tris(trimethylsilyl)silane((TMS)3SiH) acts not only as a hydrogen source, but also as an electron donor to form electron donor-acceptor (EDA) complex with redox-active esters, and the reaction involves the radical process.

Abstract

Herein, a novel protocol for visible light induced decarboxylation was reported. The method avoids the addition of radical initiators. A series of primary, secondary, and tertiary redox-active esters underwent decarboxylation efficiently, as well as amino acid and peptide derivatives. Many natural products and drug molecules containing carboxyl groups can also be transformed well. The method has mild reaction conditions, wide substrate scope, satisfactory functional group compatibility with good to excellent yields. The preliminary mechanism studies suggested that tris(trimethylsilyl)silane((TMS)3SiH) acts not only as a hydrogen source, but also as an electron donor to form electron donor-acceptor (EDA) complex with redox-active esters, and the reaction involves the radical process.