The 2,6-dimercaptoazulene motif: Efficient synthesis and completely regioselective metallation of its 6-mercapto terminus

Kolbe J. Scheetz, Andrew D. Spaeth, Alexander S. Vorushilov, Douglas R. Powell, Victor W. Day, Mikhail V. Barybin

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

2,6-Dimercapto-1,3-diethoxycarbonylazulene, a rare example of an unsymmetrical dimercaptoarene, was efficiently synthesized via two routes from common azulenic precursors. The SH-termini of this linear nonbenzenoid dimercaptan exhibit markedly different acidities, which permitted exclusively regioselective metallation of its 6-SH end with the [PPh3PAuI] fragment to afford the only mononuclear adduct (10) of a dimercaptoarene known to date. Subsequent metallation of the 2-SH terminus of 10 with another equivalent of [PPh3PAuI] gave the corresponding dinuclear AuI complex featuring the 2,6-azulenedithiolate linker. The complex constitutes a unique unsymmetrical platform for probing the exchange of gold-bound thiolates within a single compound.

Original languageEnglish (US)
Pages (from-to)4267-4272
Number of pages6
JournalChemical Science
Volume4
Issue number11
DOIs
StatePublished - Sep 30 2013

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