Fused diethynylbenzenes and phenanthrenes via arynes with alkynylsilanes. Issue 13 (25th January 2023)

• Record Type: Journal Article
• Authors: Dong, Jie; Lei, Yu; Hu, Qiong; Zong, Lingli; Zhang, Ke; Zhang, Yajuan; Hu, Yimin
• Is Part Of: Organic & biomolecular chemistry. Volume 21:Issue 13(2023)
• Page Start: 2715
• Page End: 2719
• Publication Date: 2023-01-25
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob02046g
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The concept of organosilicon in organic synthesis is applied to the hydroalkynylation and base promoted intramolecular cyclization reactions of hexadehydro-Diels–Alder-derived benzynes. Abstract : A method for the hydroalkynylation and catalytic cyclization reactions of hexadehydro-Diels–Alder-derived benzynes is described. Diethynylbenzene derivatives are generated in a one-step reaction via trimethylsilyl-alkyne groups with benzyne formed by heating the appropriate tetrayne substrate. Trimethyl(phenylethynyl)silane loses TMS and binds to the electron-deficient site on HDDA-derived benzynes, and then phenanthrene was synthesized under mild reaction conditions by transition-metal-free, base promoted intramolecular cyclization.