Ligand coupling within σ-sulphurane intermediates formed in the reaction of benzyl 2-pyridyl and related sulphoxides with Grignard reagents
- 1 January 1987
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 3,p. 405-411
- https://doi.org/10.1039/p29870000405
Abstract
The reaction of benzyl or 1-phenylethyl 2-pyridyl sulphoxide (1) or (18) with a Grignard reagent was found to give the ligand-coupling product, i.e., 2-benzylpyridine or 2-(1-phenylethyl)pyridine (2) or (22) in excellent yield. This coupling reaction was found to proceed within the σ-sulphurane formed as an intermediate upon treatment of benzyl 2-pyridyl and related sulphoxides with a Grignard reagent. The stereochemical course of this coupling reaction involves complete retention at the benzylic carbon.Keywords
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