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

Title: Electrochemically Mediated Oxidation of Sensitive Propargylic Benzylic Alcohols

Journal Article · 10 February 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.

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

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

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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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
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Title: Electrochemically Mediated Oxidation of Sensitive Propargylic Benzylic Alcohols

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