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Issue 11, 2013
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The 2,6-dimercaptoazulene motif: efficient synthesis and completely regioselective metallation of its 6-mercapto terminus

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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.

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

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Article information


Submitted
25 Jun 2013
Accepted
13 Aug 2013
First published
14 Aug 2013

Chem. Sci., 2013,4, 4267-4272
Article type
Edge Article

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

K. J. Scheetz, A. D. Spaeth, A. S. Vorushilov, D. R. Powell, V. W. Day and M. V. Barybin, Chem. Sci., 2013, 4, 4267
DOI: 10.1039/C3SC51773J

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