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Publication Details
AFRICAN RESEARCH NEXUS
SHINING A SPOTLIGHT ON AFRICAN RESEARCH
One-pot synthesis of unsymmetrical disulfides using 1-chlorobenzotriazole as oxidant: Interception of the sulfenyl chloride intermediate
Tetrahedron, Volume 66, No. 17, Year 2010
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Description
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 (aliphatic, aromatic, heteroaromatic), with a variation developed for aliphatic-aliphatic couplings. Differentially N-protected cysteines couple to afford the unsymmetrical cystine derivatives in high yield (90%), which serves as a model for the one-pot intermolecular coupling of cysteine-containing peptides to form peptide disulfide heterodimers. Minimal exchange in aromatic-aromatic disulfide synthesis is noted on account of the mild conditions. © 2010 Elsevier Ltd. All rights reserved.
Authors & Co-Authors
Stellenboom, Nashia
South Africa, Cape Town
University of Cape Town
Hunter, Roger
South Africa, Cape Town
University of Cape Town
Caira, Mino R.
South Africa, Cape Town
University of Cape Town
Statistics
Citations: 32
Authors: 3
Affiliations: 1
Identifiers
Doi:
10.1016/j.tet.2010.02.077