title: Deprotonative metalation of chloro- and bromopyridines using amido-based bimetallic species and regioselectivity-computed CH acidity relationships.
abstract: A series of chloro- and bromopyridines have been deprotometalated by using a range of 2,2,6,6-tetramethylpiperidino-based mixed lithium-metal combinations. Whereas lithium-zinc and lithium-cadmium bases afforded different mono- and diiodides after subsequent interception with iodine, complete regioselectivities were observed with the corresponding lithium-copper combination, as demonstrated by subsequent trapping with benzoyl chlorides. The obtained selectivities have been discussed in light of the CH acidities of the substrates, determined both in the gas phase and as a solution in THF by using the DFT B3LYP method.
authors: Chimie et Photonique Moléculaires, UMR 6510 CNRS, Université de Rennes 1, Bâtiment 10A, Case 1003, Campus Scientifique de Beaulieu, 35042 Rennes Cedex, France.
authors: Katia
authors: K
authors: Snégaroff
authors: Tan Tai
authors: TT
authors: Nguyen
authors: Nada
authors: N
authors: Marquise
authors: Yury S
authors: YS
authors: Halauko
authors: Philip J
authors: PJ
authors: Harford
authors: Thierry
authors: T
authors: Roisnel
authors: Vadim E
authors: VE
authors: Matulis
authors: Oleg A
authors: OA
authors: Ivashkevich
authors: Floris
authors: F
authors: Chevallier
authors: Andrew E H
authors: AE
authors: Wheatley
authors: Philippe C
authors: PC
authors: Gros
authors: Florence
authors: F
authors: Mongin