title: The Nucleophilicity of Persistent α-Monofluoromethide Anions.
abstract: α-Fluorocarbanions are key intermediates in nucleophilic fluoroalkylation reactions. Although frequently discussed, the origin of the fluorine effect on the reactivity of α-fluorinated CH acids has remained largely unexplored. We have now investigated the kinetics of a series of reactions of α-substituted carbanions with reference electrophiles to elucidate the effects of α-F, α-Cl, and α-OMe substituents on the nucleophilic reactivities of carbanions.
authors.affiliation: Loker Hydrocarbon Research Institute, Department of Chemistry, University of Southern California, Los Angeles, CA, 90089-1661, USA.
authors.forename: Zhe
authors.identifier: 0000-0003-4331-7887
authors.initials: Z
authors.lastname: Zhang
authors.affiliation: Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13 (Haus F), 81377, München, Germany.
authors.forename: Ángel
authors.initials: Á
authors.lastname: Puente
authors.affiliation: Loker Hydrocarbon Research Institute, Department of Chemistry, University of Southern California, Los Angeles, CA, 90089-1661, USA.
authors.forename: Fang
authors.identifier: 0000-0002-9192-6858
authors.initials: F
authors.lastname: Wang
authors.affiliation: Loker Hydrocarbon Research Institute, Department of Chemistry, University of Southern California, Los Angeles, CA, 90089-1661, USA.|Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, NY, 14853-1301, USA.
authors.forename: Martin
authors.identifier: 0000-0001-7645-5923
authors.initials: M
authors.lastname: Rahm
authors.affiliation: Loker Hydrocarbon Research Institute, Department of Chemistry, University of Southern California, Los Angeles, CA, 90089-1661, USA.
authors.forename: Yuncai
authors.initials: Y
authors.lastname: Mei
authors.affiliation: Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13 (Haus F), 81377, München, Germany. Herbert.Mayr@cup.uni-muenchen.de.
authors.forename: Herbert
authors.initials: H
authors.lastname: Mayr
authors.affiliation: Loker Hydrocarbon Research Institute, Department of Chemistry, University of Southern California, Los Angeles, CA, 90089-1661, USA. gprakash@usc.edu.
authors.forename: G K Surya
authors.initials: GK
authors.lastname: Prakash
keywords: carbanions; fluorine effect; fluoromethylation; linear free energy relationship; nucleophilicity