1.
Org Lett
; 18(5): 944-7, 2016 Mar 04.
Article
in English
| MEDLINE
| ID: mdl-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.