Hatch Chad E, Martin Maxwell I, Gilmartin Philip H, Xiong Lu, Beam Danielle J, Yap Glenn P A, Von Bargen Matthew J, Rosenthal Joel, Chain William J
Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, United States.
Org Lett. 2022 Feb 25;24(7):1423-1428. doi: 10.1021/acs.orglett.1c03860. Epub 2022 Feb 11.
The electrochemical oxidation of sensitive propargylic benzylic alcohols having varying substituents is reported. We describe the preparation and characterization of -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.
报道了具有不同取代基的敏感炔丙基苄醇的电化学氧化。我们描述了α-羟基四氟邻苯二甲酰亚胺（TFNHPI）的制备与表征，以及以TFNHPI作为稳定电化学介质的敏感炔丙基苄醇绿色电化学氧化方案的准高通量开发。利用炔丙基苄醇的电化学氧化开发了短合成路线，用于制备克级量的白藜芦醇天然产物，如少花瑞香酚。
