Sulfoxide-Directed Metal-Free ortho-Propargylation of Aromatics and Heteroaromatics.

Chemistry : a European Journal
Andrew J EberhartDavid J Procter

Abstract

A sulfoxide-directed, metal-free ortho-propargylation of aromatics and heteroaromatics exploits intermolecular delivery of a propargyl nucleophile to sulfur followed by an intramolecular relay to carbon. The operationally simple cross-coupling procedure is general, regiospecific with regard to the propargyl nucleophile, and shows complete selectivity for products of ortho-propargylation over allenylation. The use of secondary propargyl silanes allows metal-free ortho-coupling to form carbon-carbon bonds between aromatic and heteroaromatic rings and secondary propargylic centres. The 'safety-catch' nature of the sulfoxide directing group is illustrated in a selective, iterative double cross-coupling process. The products of propargylation are versatile intermediates and they have been readily converted into substituted benzothiophenes.

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Citations

Jan 9, 2016·Journal of the American Chemical Society·José A Fernández-SalasDavid J Procter
May 11, 2016·The Journal of Organic Chemistry·Liang HuGangguo Zhu
Jul 12, 2016·The Journal of Organic Chemistry·Immo KloseNuno Maulide
Sep 13, 2016·Journal of the American Chemical Society·Xiong XiaoQian Wan
Nov 2, 2016·Journal of the American Chemical Society·Tomoyuki YanagiAtsuhiro Osuka
Mar 1, 2017·Journal of the American Chemical Society·Li ShangBo Peng
Mar 21, 2017·Nature Communications·Harry J ShrivesDavid J Procter
May 26, 2017·Journal of the American Chemical Society·Tiezheng JiaPatrick J Walsh
Jun 21, 2016·Chemical Communications : Chem Comm·Mukund M D Pramanik, Namrata Rastogi
Oct 11, 2016·Chemical Communications : Chem Comm·José A Fernández-SalasDavid J Procter
Jun 9, 2018·Angewandte Chemie·Miles H AuklandDavid J Procter
Aug 4, 2015·Chemistry : a European Journal·Shinya OtsukaAtsuhiro Osuka
Aug 12, 2018·Chemistry : a European Journal·Susana IzquierdoAlexandr Shafir
Sep 7, 2019·Chemistry : a European Journal·Tomoyuki YanagiHideki Yorimitsu
Oct 3, 2019·Chemical Communications : Chem Comm·Xiangtai MengShenlin Huang
Jul 30, 2020·Chemical Communications : Chem Comm·Wei YangXiaoming Feng
Jul 14, 2016·Angewandte Chemie·Alexander P Pulis, David J Procter
May 11, 2017·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Hideki Yorimitsu
Mar 17, 2021·Organic Letters·Uroš TodorovićNuno Maulide
Jul 10, 2019·The Journal of Organic Chemistry·Hang LuoPingfan Li
Aug 16, 2017·Organic Letters·Hitomi KawashimaHideki Yorimitsu

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