Remote Allylation of Unactivated C(sp3)-H Bonds Triggered by Photogenerated Amidyl Radicals.

ACS Catalysis
Bin Xu, Uttam K Tambar

Abstract

The allylation reaction is a highly versatile transformation in chemical synthesis. While many elegant direct C(sp2)-H allylation reactions have been developed, the direct allylation of unactivated C(sp3)-H bonds is underdeveloped. By applying photoredox catalysis and a [1,5]-HAT process, herein we report a direct allylation of unactivated C(sp3)‒H bonds. This photocatalyzed transformation is tolerant of several functional groups in the amide and allylic chloride substrates. Various allyl-substituted amide products were obtained with good yields and high δ-selectivity.

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Citations

Feb 13, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Sergio Rodríguez-ArévaloSantiago Vázquez
Aug 7, 2019·Organic & Biomolecular Chemistry·Tongyu LiBolin Zhu
Aug 14, 2019·Chemical Society Reviews·Zhen ChenJun-An Ma
Feb 6, 2020·Chemistry, an Asian Journal·Gautam KumarIndranil Chatterjee
Mar 5, 2020·Journal of the American Chemical Society·Bin XuUttam K Tambar
Nov 23, 2019·Journal of the American Chemical Society·Xiaojun ZengWei Liu
Mar 10, 2020·Journal of the American Chemical Society·Simon CerfontaineLudovic Troian-Gautier
Feb 21, 2020·ACS Catalysis·Dian-Feng ChenGarret M Miyake
Sep 30, 2021·Chemical Reviews·Natalie Holmberg-Douglas, David A Nicewicz

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