Photocatalyst-Free Visible-Light Photoredox Dearomatization of Phenol Derivatives Containing Ketoximes: An Easy Access to Spiropyrrolines

Organic Letters
Yongzhen HanHua Fu

Abstract

A novel and simple visible-light photoredox intramolecular dearomatization of phenol derivatives containing ketoximes leading to spiropyrrolines has been developed. The protocol uses readily available 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as the base and electron-donor, visible light as the light source, and the reaction was performed well at room temperature without need of a photocatalyst. Therefore, the present method should provide a useful strategy for synthesis of spiropyrrolines.

References

May 29, 1999·Journal of Natural Products·B D Morris, M R Prinsep
Dec 26, 2001·Chemical Reviews·A R PapeE P Kündig
Dec 9, 2003·European Journal of Pharmacology·Srinivas PeddiRichard B Westkaemper
Apr 15, 2004·Bioorganic & Medicinal Chemistry Letters·Srinivas PeddiRichard B Westkaemper
Apr 9, 2008·Angewandte Chemie·Toshifumi DohiYasuyuki Kita
Jul 24, 2008·Chemical Society Reviews·Samir Z Zard
Oct 31, 2009·Bioorganic & Medicinal Chemistry·Morwenna S M PearsonJean-Bernard Behr
Dec 1, 2009·Angewandte Chemie·Kirsten Zeitler
Jun 10, 2010·Chemical Society Reviews·Jagan M R Narayanam, Corey R J Stephenson
Jun 24, 2010·Nature Chemistry·Tehshik P YoonJuana Du
Apr 21, 2011·Angewandte Chemie·Stéphane P Roche, John A Porco
May 27, 2011·Journal of the American Chemical Society·Sophie RousseauxStephen L Buchwald
Oct 7, 2011·Chemical Society Reviews·Ramon Rios
Jan 31, 2012·The Journal of Organic Chemistry·Joseph W Tucker, Corey R J Stephenson
Jun 20, 2012·Angewandte Chemie·Jun Xuan, Wen-Jing Xiao
Aug 8, 2012·Chemical Society Reviews·Lei Shi, Wujiong Xia
Jan 22, 2013·Journal of the American Chemical Society·Robert J Phipps, F Dean Toste
Mar 1, 2013·Journal of the American Chemical Society·Toshifumi DohiYasuyuki Kita
Mar 21, 2013·Chemical Reviews·Christopher K PrierDavid W C MacMillan
Apr 12, 2013·Angewandte Chemie·Durga Prasad Hari, Burkhard König
Jul 9, 2014·Chemical Reviews·Erick M Carreira, Thomas C Fessard
Jul 24, 2014·Bioorganic & Medicinal Chemistry Letters·Yajun ZhengSuresh B Singh
Dec 15, 2015·Chemistry : a European Journal·Michael J JamesWilliam P Unsworth
Feb 4, 2016·Chemical Society Reviews·Jia-Rong ChenWen-Jing Xiao
May 18, 2016·Scientific Reports·Min JiangHua Fu
Dec 10, 2016·Angewandte Chemie·Min JiangHua Fu
Sep 25, 2017·Journal of the American Chemical Society·Yunhe JinHua Fu
Oct 3, 2017·Angewandte Chemie·Thomas D SvejstrupDaniele Leonori

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