CC BY-NC-ND 4.0 · SynOpen 2021; 05(02): 152-157
DOI: 10.1055/s-0040-1706048
paper

Visible-Light-Mediated Photocatalytic Oxidative C–C Bond Cleavage of Geminal Diazides: An Approach to Oxamates

Narenderreddy Katta 
a   Catalysis & Chemical Biology Laboratory, Department of Chemistry, Indian Institute of Technology (IIT) Hyderabad, Kandi, Sangareddy, Telangana 502 285, India
,
Arumugavel Murugan 
a   Catalysis & Chemical Biology Laboratory, Department of Chemistry, Indian Institute of Technology (IIT) Hyderabad, Kandi, Sangareddy, Telangana 502 285, India
,
Sonika Sharma
b   Loyola Academy Degree & P.G College, Old Alwal, Secunderabad, Telangana 500010, India
,
Duddu S. Sharada  ∗
a   Catalysis & Chemical Biology Laboratory, Department of Chemistry, Indian Institute of Technology (IIT) Hyderabad, Kandi, Sangareddy, Telangana 502 285, India
› Author AffiliationsWe gratefully acknowledge the Council of Scientific and Industrial Research (02(0297)/17/EMR-II), Government of India and the Indian Institute of Technology Hyderabad (IITH) for financial support. N.R.K. thanks the Indian Institute of Technology Hyderabad (IITH) and the Science and Engineering Research Board, Department of Science and Technology, Ministriy of Science and Technology, India (DST-SERB), and A.V.M thanks the University Grants Committee (UGC) for the award of research rellowships.
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Dedicated to all covid-19 warriors

Abstract

Photoredox catalysis has received great attention in both academia and industry and remarkable progress has been made over the past decade. Now, it has been shown that a visible-light-mediated oxidative C–C bond cleavage of geminal diazides can be induced by organic dye catalysis for the synthesis of oxamates. A mechanistic study, confirmed by control experiments, indicates that this proceeds through single-electron transfer (SET). This methodology can be applied to convert a wide array of geminal diazides into oxamates.

Key words

photoredox - oxamates - C–C cleavage

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706048.
  • Supporting Information


Publication History

Received: 05 May 2021

Accepted after revision: 18 May 2021

Article published online:
17 June 2021

© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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