Journal
ACS CATALYSIS
Volume 9, Issue 5, Pages 4627-4631Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b00563
Keywords
allylation; C(sp(3))-H; photocatalysis; delta-selectivity; radical; [1,5]-HAT
Categories
Funding
- Welch Foundation [I-1748]
- National Institutes of Health [R01GM102604]
- American Chemical Society Petroleum Research Fund [59177-ND1]
- Teva Pharmaceuticals Marc A. Goshko Memorial Grant [60011-TEV]
- Sloan Research Fellowship
- W. W. Caruth, Jr. Endowed Scholarship
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The allylation reaction is a highly versatile transformation in chemical synthesis. While many elegant direct C(sp(2))-H allylation reactions have been developed, the direct allylation of unactivated C(sp(3))-H bonds is underdeveloped. By applying photoredox catalysis and a [1,5]-HAT process, herein we report a direct allylation of unactivated C(sp(3))-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 delta-selectivity.
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