Synlett 2019; 30(10): 1178-1182
DOI: 10.1055/s-0037-1611737
cluster
© Georg Thieme Verlag Stuttgart · New York

Electrochemical C(sp3)–H Fluorination

Yusuke Takahira
a   Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States   Email: pbaran@scripps.edu
,
Miao Chen
a   Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States   Email: pbaran@scripps.edu
,
Yu Kawamata
a   Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States   Email: pbaran@scripps.edu
,
Pavel Mykhailiuk
a   Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States   Email: pbaran@scripps.edu
b   Enamine Ltd., Chervonotkatska 78, 02094 Kyiv, , Ukraine and Taras Shevchenko National University of Kyiv, Chemistry Department, Volodymyrska 64, 01601 Kyiv, Ukraine
,
Hugh Nakamura
a   Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States   Email: pbaran@scripps.edu
,
Byron K. Peters
a   Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States   Email: pbaran@scripps.edu
,
Solomon H. Reisberg
a   Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States   Email: pbaran@scripps.edu
,
Chao Li
a   Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States   Email: pbaran@scripps.edu
,
Longrui Chen
c   Asymchem Life Science (Tianjin), Tianjin Economic-Technological Development Zone, Tianjin 300457, P. R of China
,
Tamaki Hoshikawa
d   Discovery, Medicine Creation, Neurology Business Group, Eisai Co., Ltd., 5-1-3 Tokodai, Tsukuba-shi, Ibaraki, 300-2635, Japan
,
Tomoyuki Shibuguchi
d   Discovery, Medicine Creation, Neurology Business Group, Eisai Co., Ltd., 5-1-3 Tokodai, Tsukuba-shi, Ibaraki, 300-2635, Japan
,
a   Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States   Email: pbaran@scripps.edu
› Author Affiliations

Financial support for this work was provided by the NSF (#1740656), Pfizer, AGC Inc. (to Y.T.), Nankai University (to M.C.), the George E. Hewitt Foundation (to Y.K.), a Fulbright Scholar Fellowship (to P.M.), JSPS (to H.N.), the Swedish Research Council (VR 2017-00362 to B.K.P.), NSF GRFP (#2017237151) and a Donald and Delia Baxter Fellowship (to S.H.R.).
Further Information

Publication History

Received: 23 January 2019

Accepted after revision: 27 January 2019

Publication Date:
01 March 2019 (online)


Published as part of the Cluster Electrochemical Synthesis and Catalysis

Abstract

A simple and robust method for electrochemical alkyl C–H fluorination is presented. Using a simple nitrate additive, a widely available fluorine source (Selectfluor), and carbon-based electrodes, a wide variety of activated and unactivated C–H bonds are converted into their C–F congeners. The scalability of the reaction is also demonstrated with a 100 gram preparation of fluorovaline.

Supporting Information