Electrophilic fluorination of aromatic compounds with NF type reagents: kinetic isotope effects and mechanism

Electrophilic fluorination of aromatic compounds with NF type reagents: kinetic isotope effects and mechanism Full article

Journal

Tetrahedron Letters
ISSN: 0040-4039

Output data

Year: 2006, Volume: 47, Number: 15, Pages: 2639-2642 Pages count : DOI: 10.1016/j.tetlet.2006.02.016

Tags

fluorination; NF reagent; mechanism; kinetics; deuterium isotope effects; 1,2-shift

Authors

Borodkin GI , Zaikin PA , Shubin VG

Affiliations

1	(Данные Web of science) Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia

H/D Isotope effects in fluorination of aromatic compounds with NF type reagents have been studied to reveal the reaction mechanism. The results obtained are consistent with a polar SEAr mechanism. Small deuterium isotope effects (k(H)/k(D) = 0.86-0.99) show that decomposition of a Wheland-type intermediate is not rate determining. The first example of a 1,2-hydrogen shift accompanying electrophilic fluorination of arenes has been observed in the fluorination of 1,3,5-trideuterobenzene. (c) 2006 Elsevier Ltd. All rights reserved.

Borodkin G. , Zaikin P. , Shubin V.
Electrophilic fluorination of aromatic compounds with NF type reagents: kinetic isotope effects and mechanism
Tetrahedron Letters. 2006. V.47. N15. P.2639-2642. DOI: 10.1016/j.tetlet.2006.02.016 WOS Scopus РИНЦ

Published print:

Apr 1, 2006

Web of science	WOS:000236438100041
Scopus	2-s2.0-33644914169
Elibrary	13505866
OpenAlex	W1993076381