Copper-catalyzed tandem arylation–cyclization of 2-alkynylaryl isothiocyanates with diaryliodonium salts: an efficient synthesis of thiochromeno[2, 3-b]indoles. Issue 7 (24th May 2016)

• Record Type: Journal Article
• Authors: Wen, Li-Rong; Shen, Qiang-Yu; Guo, Wei-Si; Li, Ming
• Is Part Of: Organic chemistry frontiers. Volume 3:Issue 7(2016:Jul.)
• Page Start: 870
• Page End: 874
• Publication Date: 2016-05-24
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c6qo00133e
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A Cu-catalyzed arylation–cyclization approach is developed for the synthesis of thiochromeno[2, 3- b ]indoles through the S -arylation, 5- endo-trig cyclization, and Friedel–Crafts-type cyclization sequence. Abstract : 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.