Direct alkylation of thiophenes via bis-coupling with vinyl acetates. Issue 51 (19th December 2018)

• Record Type: Journal Article
• Authors: Zhang, Tong; Wang, Nai-Xing; Wu, Yue-Hua; Yan, Zhan; Xing, Yalan; Wen, Jia-Long; Gao, Xue-Wang
• Is Part Of: Tetrahedron letters. Volume 59:Issue 51(2018)
• Page Start: 4525
• Page End: 4527
• Publication Date: 2018-12-19
• Subjects: Alkylation -- Thiophene -- Bis-coupling -- Vinyl acetate -- Iron-catalyzed; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.11.027
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: A novel direct alkylation of thiophenes via bis-coupling with vinyl acetates has been developed. To the best of our knowledge, this represents the first report of the iron-catalysed coupling of two thiophenes with vinyl groups. Utilizing earth-abundant, inexpensive, and non-toxic iron catalysts, this methodology converts simple thiophenes to symmetrical dithienylethane derivatives under mild conditions in one step. Highlights: First report of iron-catalyzed coupling of two thiophenes with vinyl groups. This method converts simple thiophenes to tertiary carbon coupled dithienylethane at room temperature. Operationally simple approach for bis-alkylation of thiophenes. Abstract: A novel direct alkylation of thiophenes via bis-coupling with vinyl acetates has been developed. To the best of our knowledge, this represents the first report of the iron-catalysed coupling of two thiophenes with vinyl groups. Utilizing earth-abundant, inexpensive, and non-toxic iron catalysts, this methodology converts simple thiophenes to symmetrical dithienylethane derivatives under mild conditions in one step.