Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 27, Pages 10859-10863Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202001571
Keywords
carbazate; deoxgenative alkylation; electrochemistry; radical fragmentation
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Funding
- National Natural Science Foundation of China [21772085, 21971107]
- Collaborative Innovation Center of Solid-State Lighting and Energy-Saving Electronics of Nanjing University
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The C-O bond cleavage for activation of alcohols is synthetically useful and practically challenging. This work describes carbazate as a new type of electrochemically activated alkylating agent derived from ubiquitous alcohols for direct functionalization of heteroarenes under mild electrolytic conditions. The simple undivided cell at low oxidative potentials with carbon/platinum electrode set-ups offers excellent substrate tolerance, affording a variety of primary, secondary and tertiary alkyl-decorated heterocycles in good chemical yields. Furthermore, the mechanism for this electrochemical deoxyalkylation reaction has been investigated.
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