Selective 1,2-Aminoisothiocyanation of 1,3-Dienes Under Visible-Light Photoredox Catalysis.

Angewandte Chemie
Weisi GuoJieping Zhu

Abstract

Selective three-component 1,2-diamination of 1,3-dienes with concurrent introduction of two orthogonally protected amino groups remains unknown despite its significant synthetic potential. We report herein that reaction of conjugated dienes with N-aminopyridinium salts and TMSNCS affords 1,2-aminoisothiocyanation products in a highly chemo- and regio-selective manner under mild photoredox catalytic conditions. Mechanistic studies indicate that the facile isomerization of allyl thiocyanates to allyl isothiocyanates under photocatalytic conditions is responsible for the selective formation of the observed products. The mild isomerization protocol is expected to find applications in the synthesis of allyl isothiocyanates in a broad sense.

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Citations

Jan 1, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Hongjun YaoWei Zhang
Mar 12, 2021·Journal of the American Chemical Society·Fu-Dong LuWen-Jing Xiao
Mar 19, 2021·Organic & Biomolecular Chemistry·Ziying WuHuanfeng Jiang
Apr 24, 2021·Beilstein Journal of Organic Chemistry·Zhonglie YangJiahong Li
Jun 11, 2021·Organic Letters·Qi XuYifei Li

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