Copper-catalyzed tandem arylation–cyclization of 2-alkynylaryl isothiocyanates with diaryliodonium salts: an efficient synthesis of thiochromeno[2,3-b]indoles

文献情報

出版日 2016-05-18

DOI 10.1039/C6QO00133E

インパクトファクター 5.281

著者

Li-Rong Wen, Qiang-Yu Shen, Wei-Si Guo, Ming Li

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要旨

A catalytic tandem arylation–cyclization approach using 2-alkynylphenyl isothiocyanates with diaryliodonium salts is described. The reaction is performed under mild conditions and thiochromeno[2,3-b]indoles are obtained in moderate to good yields. This tandem protocol involves chemoselective S-arylation, regioselective 5-endo-trig cyclization and Friedel–Crafts-type cyclization processes. Two C–C bonds, one C–S bond, and two heterocyclic rings are formed in a single step. Preliminary mechanistic studies indicate that a carbocation mechanism is involved.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Copper-catalyzed tandem arylation–cyclization of 2-alkynylaryl isothiocyanates with diaryliodonium salts: an efficient synthesis of thiochromeno[2,3-b]indoles

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