Catalytic Alkene Difunctionalization via Imidate Radicals

Journal of the American Chemical Society
Kohki M NakafukuDavid A Nagib

Abstract

The first catalytic strategy to harness imidate radicals has been developed. This approach enables alkene difunctionalization of allyl alcohols by photocatalytic reduction of their oxime imidates. The ensuing imidate radicals undergo consecutive intra- and intermolecular reactions to afford (i) hydroamination, (ii) aminoalkylation, or (iii) aminoarylation, via three distinct radical mechanisms. The broad scope and utility of this catalytic method for imidate radical reactivity is presented, along with comparisons to other N-centered radicals and complementary, closed-shell imidate pathways.

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Citations

Sep 19, 2019·Chemical Communications : Chem Comm·Yong-Hong LiShang-Dong Yang
Nov 14, 2019·Organic & Biomolecular Chemistry·Rima ThakurAmit Kumar
May 23, 2019·Angewandte Chemie·Dirk Leifert, Armido Studer
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Jan 7, 2020·Chemical Communications : Chem Comm·Zhuming SunHugh Y Zhu
Feb 15, 2020·Chemical Society Reviews·Heng Jiang, Armido Studer
Sep 24, 2020·Organic & Biomolecular Chemistry·Chengkou LiuKai Guo
Apr 19, 2019·Chemical Science·Leah M StatemanDavid A Nagib
Mar 21, 2020·Nature Communications·Quanping GuoZhaoqing Xu
Feb 9, 2020·Nature Communications·Xuzhong ShenZhan Lu
Jun 24, 2020·Nature Chemistry·Kohki M NakafukuDavid A Nagib
Jan 30, 2021·Chemical Communications : Chem Comm·Xiaojing LaiGuanyinsheng Qiu
Jan 8, 2021·The Journal of Organic Chemistry·Zhengqiang FuNing Liu
Mar 25, 2021·The Journal of Organic Chemistry·Lu-Wen ZhangWei He
Apr 30, 2021·Chemical Communications : Chem Comm·Jin-Biao LiuGuanyinsheng Qiu
Jan 31, 2020·Chemical Science·Andrew D ChenDavid A Nagib
Jun 18, 2021·Organic Letters·Ayham H AbazidBoris J Nachtsheim
Aug 6, 2021·The Journal of Physical Chemistry. B·Shingo HattoriKazuteru Shinozaki
Aug 6, 2021·Physical Chemistry Chemical Physics : PCCP·Maciej WitwickiAndrew Ozarowski
May 10, 2019·Journal of the American Chemical Society·Hongze LiHao Xu
Mar 7, 2020·Journal of the American Chemical Society·Allen F PrusinowskiDavid A Nagib
Jun 28, 2019·Journal of the American Chemical Society·Kaining ZhangZhiwei Zuo
Jun 11, 2019·Journal of the American Chemical Society·Seung Youn Hong, Sukbok Chang
Sep 13, 2019·The Journal of Organic Chemistry·Kohki M NakafukuDavid A Nagib
May 16, 2019·The Journal of Organic Chemistry·Lin Wang, Chuan Wang

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