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Updated: Jun 25, 2026

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
Synthesis and stereoselective halogenolysis of optically pure benzylstannanes
José L García Ruano1, José Alemán, Alejandro Parra
1Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco 28049 Madrid, Spain. joseluis.garcia.ruano@uam.es
Abstract:
In this work we show that lithium ortho-sulfinyl benzylcarbanions are highly efficient reagents for the synthesis of optically pure benzylstannanes by reacting with halotriorganyl tin (up to >98:2 dr). The stereoselectivity of these reactions is opposite to those observed with carbon electrophiles. Bromolysis of the obtained ortho-sulfinylbenzylstannanes with Br(2) in the presence of CuBr takes place in a highly stereoselective way (up to 90:10 dr) with retention of the configuration, which allows the synthesis of optically pure 2-sulfinylated benzyl bromides. Different experiments support the proposed mechanistic rationalization for both processes.
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