Tuning Triplet Energy Transfer of Hydroxamates as the Nitrene Precursor for Intramolecular C(sp3 )-H Amidation

Journal of the American Chemical Society
Hoimin JungSukbok Chang

Abstract

Reported herein is the design of a photosensitization strategy to generate triplet nitrenes and its applicability for the intramolecular C-H amidation reactions. Substrate optimization by tuning physical organic parameters according to the proposed energy transfer pathway led us to identify hydroxamates as a convenient nitrene precursor. While more classical nitrene sources, representatively organic azides, were ineffective under the current photosensitization conditions, hydroxamates, which are readily available from alcohols or carboxylic acids, are highly efficient in accessing synthetically valuable 2-oxazolidinones and γ-lactams by visible light. Mechanism studies supported our working hypothesis that the energy transfer path is mainly operative.

References

Oct 13, 2005·Journal of the American Chemical Society·Hélène LebelSylvain Lectard
Jul 24, 2008·Chemical Society Reviews·Samir Z Zard
May 28, 2009·Angewandte Chemie·Christiane MüllerThorsten Bach
Jun 26, 2012·Angewandte Chemie·Geoffroy DequirezPhilippe Dauban
Nov 28, 2013·Angewandte Chemie·Elliot P Farney, Tehshik P Yoon
Mar 24, 2016·Angewandte Chemie·Matthew N HopkinsonFrank Glorius
Jun 9, 2016·Journal of the American Chemical Society·Andreas TrösterThorsten Bach
Jun 22, 2016·Journal of the American Chemical Society·Jacob DaviesDaniele Leonori
Oct 23, 2016·Chemistry : a European Journal·Xiang RenZhan Lu
Jan 5, 2017·Chemical Reviews·Yoonsu ParkSukbok Chang
Apr 20, 2017·Organic & Biomolecular Chemistry·Hélène LebelMatthias Ernzerhof
Jul 5, 2017·Chemistry : a European Journal·Petrus F KuijpersBas de Bruin
Oct 13, 2017·Journal of the American Chemical Society·Dian-Feng ChenTomislav Rovis
Feb 1, 2015·Chemical Science·E BrachetB König
May 19, 2018·Angewandte Chemie·Quan-Quan ZhouWen-Jing Xiao
May 23, 2018·Chemistry : a European Journal·Jacob DaviesDaniele Leonori
Aug 8, 2018·Nature Chemistry·Michael TedersFrank Glorius
Aug 9, 2018·Chemical Society Reviews·Felix Strieth-KalthoffFrank Glorius
Apr 13, 2019·Journal of the American Chemical Society·Hao WangGong Chen
Apr 17, 2019·The Journal of Organic Chemistry·Peter BellottiEtienne Brachet
May 31, 2019·Journal of the American Chemical Society·Mary Elisabeth DaubTehshik P Yoon
Aug 27, 2019·Journal of the American Chemical Society·Hoimin JungSukbok Chang
Dec 2, 2019·Chemical Science·Evan M SherbrookTehshik P Yoon

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