Journal
ORGANIC LETTERS
Volume 23, Issue 3, Pages 722-726Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c03944
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Funding
- NSFC [21821003]
- Sun Yat-Sen University
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The unactivated C(sp(3))-H heteroarylation of free alcohol at the delta position was achieved through a radical procedure catalyzed by silver salt under gentle thermal conditions in water. Protonic acids and Lewis acids were found to efficiently activate pyridines for this Minisci-type reaction. The reaction showed good functional group tolerance and substrate scope, with terminal secondary and tertiary alcohols being suitable substrates. Both electron-donating and -withdrawing groups on the electron-deficient heteroarene substrates yielded the target products in moderate to good yields. The study also included a successful gram-scale experiment and radical blocking/experiment experiments to support the radical mechanism.
Catalyzed by silver salt, the unactivated C(sp(3))-H heteroarylation of free alcohol at the delta position is realized under gentle thermal conditions in water through a radical procedure. Both protonic acids and Lewis acids are found to be efficient for activating pyridines for this Minisci-type reaction. The reaction enjoys a good functional group tolerance and substrate scope. Terminal secondary and tertiary alcohols are suitable substrates. With either electron-donating or -withdrawing groups, the electron-deficient heteroarene substrates generate the target products in moderate to good yields. A gram-scale experiment can be successfully operated. A radical blocking experiment and a radical clock experiment are studied to support the radical mechanism.
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