Modular synthesis of (E)-cinnamaldehydes directly from allylarenes via a metal-free DDQ-mediated oxidative processElectronic supplementary information (ESI) available. See DOI: 10.1039/c8ob01469h

An efficient synthesis of ( E )-cinnamaldehydes by a metal-free DDQ-mediated oxidative transformation of allylarenes was developed. The protocol provides a practical method to prepare diverse ( E )-cinnamaldehydes with broad functional group tolerance in good to excellent yields, including easy acce...

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Main Authors: Xu, Ting-Ting, Jiang, Tao-Shan, Han, Xiao-Lan, Xu, Yuan-Hong, Qiao, Jin-Ping
Format: Article
Language:English
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Summary:An efficient synthesis of ( E )-cinnamaldehydes by a metal-free DDQ-mediated oxidative transformation of allylarenes was developed. The protocol provides a practical method to prepare diverse ( E )-cinnamaldehydes with broad functional group tolerance in good to excellent yields, including easy access to natural products randainal and geranyloxy sinapyl aldehyde from plant extracts. Finally, the mechanism of a single-electron transfer process was proposed. A practical route to prepare ( E )-cinnamaldehydes and natural products randainal and geranyloxy sinapyl aldehyde has been achieved via a metal-free DDQ-mediated oxidative transformation of allylarenes.
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob01469h