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Direct Preparation of 3-Iodochromenes From 3-Aryl- And 3-Alkyl-2-propyn-1-ols With Diaryliodonium Salts and NIS

Direct Preparation of 3-Iodochromenes From 3-Aryl- And 3-Alkyl-2-propyn-1-ols With Diaryliodonium Salts and NIS

Teppei Sasaki, Kotaro Miyagi, Katsuhiko Moriyama, Hideo Togo

Org Lett. 2016 Mar 4;18(5):944-7.

PMID: 26886081

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP66003767	Diphenyliodonium triflate		66003-76-7	Price

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