Methylene Blue-Catalyzed Oxidative Cleavage of N-Carbonylated Indoles

Kui Wu; Cheng Fang; Sarbjeet Kaur; Peng Liu; Ting Wang

doi:10.1055/s-0036-1592006

Synthesis, Inhaltsverzeichnis

Synthesis 2018; 50(15): 2897-2907
DOI: 10.1055/s-0036-1592006

special topic

Methylene Blue-Catalyzed Oxidative Cleavage of N-Carbonylated Indoles

Kui Wu

^aDepartment of Chemistry, University at Albany, State University of New York, 1400 Washington Avenue, Albany, New York 12222, United States eMail: twang3@albany.edu

,

Cheng Fang

^bDepartment of Chemistry, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, PA 15260, United States eMail: pengliu@pitt.edu

^cComputational Modeling & Simulation Program, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, PA 15260, United States

,

Sarbjeet Kaur

^aDepartment of Chemistry, University at Albany, State University of New York, 1400 Washington Avenue, Albany, New York 12222, United States eMail: twang3@albany.edu

,

Peng Liu*

^bDepartment of Chemistry, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, PA 15260, United States eMail: pengliu@pitt.edu

,

Ting Wang *

^aDepartment of Chemistry, University at Albany, State University of New York, 1400 Washington Avenue, Albany, New York 12222, United States eMail: twang3@albany.edu

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Abstract

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

Abstract

The development of a visible-light-mediated oxidative cleavage of electron-deficient indoles is reported. Methylene blue serves as an effective catalyst and the transformation shows a broad substrate scope. A variety of functional groups are well accommodated in the mild reaction conditions. The photo-mediated single electron transfer and oxidative cleavage mechanisms were investigated via density functional theory and Marcus theory calculations.

Key words

methylene blue - visible light - electron-deficient indoles - Witkop–Winterfeldt oxidation - photocatalysis

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Referenzen

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