Tetrahedron

One-pot synthesis of unsymmetrical disulfides using 1-chlorobenzotriazole as oxidant: Interception of the sulfenyl chloride intermediate

N Stellenboom, R Hunter, MR Caira

Index: Stellenboom, Nashia; Hunter, Roger; Caira, Mino R. Tetrahedron, 2010 , vol. 66, # 17 p. 3228 - 3241

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Citation Number: 15

Abstract

A high-yielding and low temperature one-pot procedure is described for unsymmetrical disulfide synthesis from two different thiols using 1-chlorobenzotriazole (BtCl) as oxidant. The mechanism of the coupling involves in situ trapping of the sulfenyl chloride intermediate R1SCl by nucleophilic benzotriazole (BtH) to form R1SBt, which protects R1SCl from forming the homodimer R1SSR1. The methodology is applicable to all types of thiol ( ...