Photoredox-Catalyzed C-H Arylation of Internal Alkenes to Tetrasubstituted Alkenes: Synthesis of Tamoxifen

Organic Letters
Quannan WangZhengkun Yu

Abstract

Visible-light-induced direct C-H arylation of S,S-functionalized internal alkenes, that is, α-oxo ketene dithioacetals and analogues, has been efficiently realized with aryldiazonium salts (ArN2BF4) as coupling partners and Ru(bpy)3Cl2·6H2O as photosensitizer at ambient temperature. The strategy to activate the internal olefinic C-H bond by both the alkylthio and electron-withdrawing functional groups was investigated. The synthetic protocol was successfully applied to the synthesis of all-carbon tetrasubstituted alkenes including tamoxifen.

References

Feb 16, 2000·European Journal of Cancer : Official Journal for European Organization for Research and Treatment of Cancer (EORTC) [and] European Association for Cancer Research (EACR)·A S Levenson, V C Jordan
Dec 4, 2003·Journal of the American Chemical Society·Kenichiro ItamiJun-ichi Yoshida
Oct 4, 2007·Journal of the American Chemical Society·Yasushi NishiharaKentaro Takagi
Nov 2, 2007·Chemical Reviews·Alison B Flynn, William W Ogilvie
Sep 10, 2009·Angewandte Chemie·Ikuhiro NagaoTamejiro Hiyama
Oct 20, 2012·Chemical Society Reviews·Liandi WangZhengkun Yu
Nov 14, 2012·Chemical Society Reviews·Ling PanQun Liu
May 7, 2014·Chemical Communications : Chem Comm·Qin YangZhengkun Yu
May 8, 2014·Organic Letters·Jie Tang, Lukas J Goossen
Sep 17, 2015·Chemistry : a European Journal·Xiaoge YangZhengkun Yu
Dec 31, 2015·Journal of the American Chemical Society·Jan B Metternich, Ryan Gilmour
Mar 11, 2016·Angewandte Chemie·Fanzhi YangLutz Ackermann
Aug 3, 2016·Accounts of Chemical Research·Indrajit GhoshBurkhard König
Sep 27, 2016·Angewandte Chemie·Mickel J HansenBen L Feringa
Oct 14, 2016·Chemistry : a European Journal·Enrico La CasciaElena Fernández
Jan 27, 2017·Chemical Reviews·Zhe DongGuangbin Dong
Mar 3, 2017·Journal of the American Chemical Society·Barry M TrostNicolas Quach
Apr 21, 2017·Nature·Jacob T EdwardsPhil S Baran
May 20, 2017·Chemistry : a European Journal·Jiangwei WenAiwen Lei
Jun 21, 2017·Organic & Biomolecular Chemistry·Zhuqing LiuZhengkun Yu
Aug 12, 2017·Journal of the American Chemical Society·Stefan KraftRobert B Kargbo

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Citations

May 28, 2020·Chemical Society Reviews·Jiang LouZhengkun Yu

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