title: Triethylborane-initiated radical chain fluorination: a synthetic method derived from mechanistic insight.
abstract: We offer a mild, metal-free sp(3) C-H fluorination alternative using Selectfluor and a substoichiometric amount of triethylborane--an established radical initiator in the presence of O2. This radical-chain-based synthetic method is particularly noteworthy as an offspring of the insight gained from a mechanistic study of copper-promoted aliphatic fluorination, constructively turning O2 from an enemy to an ally. Furthermore, BEt3/O2 is a preferred initiator in industrial processes, as it is economical, is low in toxicity, and lends way to easier workup.
authors.affiliation: Department of Chemistry, Johns Hopkins University , 3400 North Charles Street, Baltimore, Maryland 21218, United States.
authors.forename: Cody Ross
authors.initials: CR
authors.lastname: Pitts
authors.forename: Bill
authors.initials: B
authors.lastname: Ling
authors.forename: Ryan
authors.initials: R
authors.lastname: Woltornist
authors.forename: Ran
authors.initials: R
authors.lastname: Liu
authors.forename: Thomas
authors.initials: T
authors.lastname: Lectka