Open AccessElectrochemically Mediated Oxidation of Sensitive Propargylic Benzylic Alcohols
Author(s) -
Chad Hatch,
Maxwell I. Martin,
Philip H. Gilmartin,
Lu Xiong,
Danielle J Beam,
Glenn P. A. Yap,
Matthew J Von Bargen,
Joel Rosenthal,
William J. Chain
Publication year - 2022
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.1c03860
Subject(s) - chemistry , electrochemistry , combinatorial chemistry , alcohol oxidation , resveratrol , organic chemistry , catalysis , electrode , biochemistry
The electrochemical oxidation of sensitive propargylic benzylic alcohols having varying substituents is reported. We describe the preparation and characterization of N -hydroxytetrafluorophthalimide (TFNHPI) and pseudo-high-throughput development of a green electrochemical oxidation protocol for sensitive propargylic benzylic alcohols that employs TFNHPI as a stable electrochemical mediator. The electrochemical oxidation of propargylic benzylic alcohols was leveraged to develop short synthetic pathways for preparing gram quantities of resveratrol natural products such as pauciflorols.