J. Dhau, Amritpal S. Singh, Yoganjaneyulu Kasetti
Dec 2, 2013
Citations
0
Influential Citations
12
Citations
Journal
Tetrahedron
Abstract
Abstract The BF3-directed lithiation of 3-chloro- and 3-bromopyridine (1a and 1b, respectively) has been investigated. The reactions of 3-chloro- or 3-bromopyridine–BF3 adduct with LDA (1.3/1.1 equiv) followed by quenching with benzaldehyde or iodine exclusively gave the C-2 substituted products. However, when 2.2 equiv of LDA and dimethyl disulfide was used, a C-6 substituted product was obtained. Dilithiation of 1a and 1b has been studied with and without the involvement of BF3 complexation. The role of Li⋯F(BF3) interactions has been investigated by experimental and DFT calculations.