Journal
ORGANIC LETTERS
Volume 21, Issue 7, Pages 2360-2364Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b00633
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Funding
- NSFC [21702182, 21873081, 21873055, 21702119]
- Chinese Thousand Youth Talents Plan
- Fundamental Research Funds for the Central Universities
- China Postdoctoral Science Foundation [2018M640546]
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We discovered a cooperative gold/silver catalysis mechanism in the oxidative cross-coupling reaction between 1,2,4,5-tetrafluorobenzene and N-TIPS-indole, using DFT calculations. A silver(I)-catalyzed CMD mechanism is responsible for the C-H activation of 1,2,4,5-tetrafluorobenzene, and C-H acidity determines the chemoselectivity. A gold(III)-catalyzed S(E)2Ar mechanism is responsible for the C3-H activation of N-TIPS-indole, and arene nucleophilicity determines the chemo- and regioselectivity. The orthogonal chemoselectivity control provides a mechanistic guide for dual C-H activation reactions.
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