☆ 4.7 Article

A Metal-Free Sulfenylation and Bromosulfenylation of Indoles: Controllable Synthesis of 3-Arylthioindoles and 2-Bromo-3-arylthioindoles

ADVANCED SYNTHESIS & CATALYSIS (2012)

Journal

ADVANCED SYNTHESIS & CATALYSIS

Volume 354, Issue 11-12, Pages 2123-2128

Publisher

WILEY-V C H VERLAG GMBH

DOI: 10.1002/adsc.201200227

Keywords

3-arylthioindoles; 2-bromo-3-arylthioindoles; bromosulfenylation; metal-free conditions; sulfenylation

Categories

Chemistry, Applied Chemistry, Organic

Funding

National Natural Science Foundation of China [21102105, 21172175]

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Abstract

An efficient metal-free sulfenylation of indoles with disulfides has been developed, leading to 3-arylthioindoles in moderate to excellent yields. Furthermore, bromosulfenylation of indoles with disulfides has been realized for the first time providing a new family of 2-bromo-3-arylthioindole derivatives in good yield by the one-pot construction of C-S and C-Br bonds. It is noteworthy that the system enables the use of both the RS moieties in RSSR and shows a broad functional group tolerance.

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