Visible-Light-Mediated Synthesis of Oxidized Amides via Organic Photoredox Catalysis

Yuliu Du; Zheng Wei; Ting Wang

doi:10.1055/s-0036-1591988

Synthesis, Table of Contents

Synthesis 2018; 50(17): 3379-3386
DOI: 10.1055/s-0036-1591988

special topic

Visible-Light-Mediated Synthesis of Oxidized Amides via Organic Photoredox Catalysis

Yuliu Du

Department of Chemistry, University at Albany, State University of New York, 1400 Washington Avenue, Albany, NY 12222, USA Email: twang3@albany.edu

,

Zheng Wei

Department of Chemistry, University at Albany, State University of New York, 1400 Washington Avenue, Albany, NY 12222, USA Email: twang3@albany.edu

,

Ting Wang *

Department of Chemistry, University at Albany, State University of New York, 1400 Washington Avenue, Albany, NY 12222, USA Email: twang3@albany.edu

› Author Affiliations

Abstract

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Published as part of the Special Topic Photoredox Methods and their Strategic Applications in Synthesis

Abstract

The development of visible-light-mediated synthesis of oxidized amides is reported. The reaction shows a broad substrate scope and highlights a mild nature of the reaction conditions. A range of functional groups are well tolerated in the reaction. Relying on the strategy, a variety of α-alkoxy amino acids are synthesized.

Key words

visible light - organic photoredox catalysis - oxidized amides - α-alkoxy amino - acids - rhodamine 6G

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References

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17 The 5-methoxy-2,4-dimethyloxazole (1a) was synthesized from commercially available N-acetyl-l-alanine methyl ester via a cyclodehydration procedure (Scheme 5). For references related to the syntheses of oxazole substrates, see the Supporting Information.

18a Crystal data for 3l: C₁₇H₂₀BrNO₄, monoclinic, P2₁/c; a = 7.0075(7) Å, b = 10.9379(3) Å, c = 27.4093(8) Å; α = 90°, β = 90.601(2)°, γ = 90°; V = 1739.7(3) Å³; Z = 4, Z′ = 1; R ₁ = 4.22%. See also the Supporting Information.
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Supplementary Material

Supporting Information