Electrochemically Mediated Oxidation of Sensitive Propargylic Benzylic Alcohols

Hatch, Chad E.; Martin, Maxwell I.; Gilmartin, Philip H.; Xiong, Lu; Beam, Danielle J.; Yap, Glenn A.; Von Bargen, Matthew J.; Rosenthal, Joel; Chain, William J.

doi:10.1021/acs.orglett.1c03860

Electrochemically Mediated Oxidation of Sensitive Propargylic Benzylic Alcohols

Journal Article · Thu Feb 10 23:00:00 EST 2022 · Organic Letters

DOI:https://doi.org/10.1021/acs.orglett.1c03860· OSTI ID:2510462

Hatch, Chad E. ^[1]; Martin, Maxwell I. ^[1]; ^[1]; Xiong, Lu ^[1]; Beam, Danielle J. ^[1]; ^[1]; Von Bargen, Matthew J. ^[1]; ^[1]; ^[1]

University of Delaware, Newark, DE (United States)

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. Here, 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.

View Accepted Manuscript (DOE)

Research Organization:: University of Delaware, Newark, DE (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF); National Institutes of Health (NIH)

Grant/Contract Number:: SC0021068

OSTI ID:: 2510462

Journal Information:: Organic Letters, Journal Name: Organic Letters Journal Issue: 7 Vol. 24; ISSN 1523-7060

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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