Dhau, Jaspreet S. ; Singh, Amritpal ; Kasetti, Yoganjaneyulu ; Bhatia, Sonam ; Bharatam, Prasad V. ; Brandão, Paula ; Félix, Vítor ; Singh, Kamal N. (2013) A study on the BF3 directed lithiation of 3-chloro- and 3-bromopyridine Tetrahedron, 69 (48). pp. 10284-10291. ISSN 0040-4020
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Official URL: http://doi.org/10.1016/j.tet.2013.10.026
Related URL: http://dx.doi.org/10.1016/j.tet.2013.10.026
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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier B.V. |
| Keywords: | 3-Chloropyridine; 3-Bromopyridine; Lithiation; Density Functional Calculation. |
| ID Code: | 116454 |
| Deposited On: | 12 Apr 2021 09:45 |
| Last Modified: | 12 Apr 2021 09:45 |
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