title: Direct Preparation of 3-Iodochromenes from 3-Aryl- and 3-Alkyl-2-propyn-1-ols with Diaryliodonium Salts and NIS.
abstract: On the basis of a study of the O-phenylation of 3-phenyl-2-propyn-1-ol with diphenyliodonium triflate and t-BuONa, a variety of 4-aryl-3-iodo-2H-benzopyrans were prepared in good to moderate yields in one pot from the reaction of 3-aryl-2-propyn-1-ols with diaryliodonium triflates and t-BuONa, followed by the treatment with N-iodosuccinimide and BF3·OEt2, under transition-metal-free and mild conditions. The formed 4-phenyl-3-iodo-2H-benzopyran was converted into 4-phenyl-2H-benzopyran derivatives through C-C bond formations at the 3-position by Pd-catalyzed coupling reactions and into coumarin with oxidants.
authors.affiliation: Graduate School of Science, Chiba University , Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan.
authors.forename: Teppei
authors.initials: T
authors.lastname: Sasaki
authors.affiliation: Graduate School of Science, Chiba University , Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan.
authors.forename: Kotaro
authors.initials: K
authors.lastname: Miyagi
authors.affiliation: Graduate School of Science, Chiba University , Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan.|Molecular Chirality Research Center, Chiba University , Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan.
authors.forename: Katsuhiko
authors.initials: K
authors.lastname: Moriyama
authors.affiliation: Graduate School of Science, Chiba University , Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan.
authors.forename: Hideo
authors.initials: H
authors.lastname: Togo
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry*; D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003374:Coumarins / Q000737:chemistry; D006847:Hydrocarbons, Iodinated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D016877:Oxidants / Q000737:chemistry; D020005:Propanols / Q000737:chemistry*; D012492:Salts; D013388:Succinimides / Q000737:chemistry
chemical_list: D000480:Alkynes; D001578:Benzopyrans; D003374:Coumarins; D006847:Hydrocarbons, Iodinated; D016877:Oxidants; D020005:Propanols; D012492:Salts; D013388:Succinimides; C008155:N-iodosuccinimide; C028255:propargyl alcohol