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Synthesis 2018; 50(15): 2897-2907
DOI: 10.1055/s-0036-1592006
special topic
© Georg Thieme Verlag Stuttgart · New York

Methylene Blue-Catalyzed Oxidative Cleavage of N-Carbonylated Indoles

Kui Wu
a   Department 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
b   Department of Chemistry, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, PA 15260, United States   Email: pengliu@pitt.edu
c   Computational Modeling & Simulation Program, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, PA 15260, United States
,
Sarbjeet Kaur
a   Department 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*
b   Department of Chemistry, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, PA 15260, United States   Email: pengliu@pitt.edu
,
Ting Wang  *
a   Department of Chemistry, University at Albany, State University of New York, 1400 Washington Avenue, Albany, New York 12222, United States   Email: twang3@albany.edu
› Author AffiliationsT.W. is grateful to the University at Albany, State University of New York, for financial support. P. L. thanks the National Science Foundation (CHE-1654122) for financial support.
Further Information

Publication History

Received: 27 January 2018

Accepted after revision: 09 April 2018

Publication Date:
08 May 2018 (online)

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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1592006.
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