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Review
. 2011 Jan 17;16(1):590-608.
doi: 10.3390/molecules16010590.

Transition metal catalyzed synthesis of aryl sulfides

Chad C Eichman  1 , James P Stambuli
Affiliations
Review

Transition metal catalyzed synthesis of aryl sulfides

Chad C Eichman et al. Molecules. .

Abstract

The presence of aryl sulfides in biologically active compounds has resulted in the development of new methods to form carbon-sulfur bonds. The synthesis of aryl sulfides via metal catalysis has significantly increased in recent years. Historically, thiolates and sulfides have been thought to plague catalyst activity in the presence of transition metals. Indeed, strong coordination of thiolates and thioethers to transition metals can often hinder catalytic activity; however, various catalysts are able to withstand catalyst deactivation and form aryl carbon-sulfur bonds in high-yielding transformations. This review discusses the metal-catalyzed arylation of thiols and the use of disulfides as metal-thiolate precursors for the formation of C-S bonds.

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Figures

Figure 1
Figure 1
Aryl sulfide-containing pharmaceuticals.
Scheme 1
Scheme 1
General mechanism for Pd-catalyzed arylthioether synthesis.
Scheme 2
Scheme 2
Potential pathway for the formation of aryl sulfides in the Fukuyama reaction.
Scheme 3
Scheme 3
Mechanism of the palladium-catalyzed arylation of cysteine.
Scheme 4
Scheme 4
Mechanistic details for Josiphos-ligated Pd-catalyzed C-S bond formation.
Scheme 5
Scheme 5
Mechanism of C-S bond formation using aryl mesylates.
Scheme 6
Scheme 6
Catalytic cycle for nickel-catalyzed aryl thioether synthesis using disulfides.
Scheme 7
Scheme 7
Catalytic cycle for the coupling of thioimides with boronic acids.
Scheme 8
Scheme 8
Cobalt-catalyze arylation of thiols
See this image and copyright information in PMC

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