Electrochemically Mediated Oxidation of Sensitive Propargylic Benzylic Alcohols | Zendy

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

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Electrochemically 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 , resveratrol , alcohol oxidation , 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.

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