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I2-Catalyzed sulfenylation of indoles and pyrroles using triethylammonium thiolates as sulfenylating agents.

ABSTRACT: Readily available triethylammonium thiolates were proven to be new and eco-friendly sulfenylating agents for the efficient and practical construction of sulfenylated indoles and pyrroles (48 examples) with good to excellent yields under metal-free and microwave irradiation conditions. The combination of I2 and DMSO enabled direct C-S bond formation, allowing easy and low-cost access to new functionalized C,S-tethered bisindoles and pyrrole-indole pairs with a wide diversity of substituents. The mechanism involving S-S and S-I bond-forming/breaking events was proposed.

SUBMITTER: Fan W

PROVIDER: S-EPMC5624724 | biostudies-literature | 2017 Jun

REPOSITORIES: biostudies-literature

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I2-Catalyzed sulfenylation of indoles and pyrroles using triethylammonium thiolates as sulfenylating agents.

Fan Wei W Yang Zhen Z Jiang Bo B Li Guigen G

Organic chemistry frontiers : an international journal of organic chemistry 20170220 6

Readily available triethylammonium thiolates were proven to be new and eco-friendly sulfenylating agents for the efficient and practical construction of sulfenylated indoles and pyrroles (48 examples) with good to excellent yields under metal-free and microwave irradiation conditions. The combination of I2 and DMSO enabled direct C-S bond formation, allowing easy and low-cost access to new functionalized C,S-tethered bisindoles and pyrrole-indole pairs with a wide diversity of ...[more]

PMID: 28983405

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