1478090-75-3Relevant academic research and scientific papers
A study on the BF3 directed lithiation of 3-chloro- and 3-bromopyridine
Dhau, Jaspreet S.,Singh, Amritpal,Kasetti, Yoganjaneyulu,Bhatia, Sonam,Bharatam, Parsad V.,Brand?o, Paula,Félix, Vítor,Singh, Kamal N.
, p. 10284 - 10291 (2013)
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 Lia?F(BF3) interactions has been investigated by experimental and DFT calculations.
