Palladium- and copper-catalyzed highly selective mono-coupling between 2,6-diiodoanisoles and terminal alkynes in the production of alkynylated anisoles as potential precursors of benzo[b]furans

Abstract

The coupling reaction between 2,6-diiodoanisoles and terminal alkynes using Pd(PPh3)2Cl2 and CuI as catalysts and diisopropylamine as base in toluene at room temperature for 12 h produced selectively alkynylated 2-iodoanisoles, in good to excellent yields (52-95%), which are useful building blocks with potential application in the synthesis of functionalized benzo[b]furans.

A reação de acoplamento entre 2,6-diiodoanisóis e alcinos terminais usando Pd(PPh3)2Cl2 e CuI como catalisadores e diisopropilamina como base em tolueno a temperatura ambiente por 12 h produziu seletivamente 2-iodoanisóis aquinilados, em rendimentos de bons a excelentes (52-95%), os quais são blocos de construção úteis com potencial aplicação na síntese de benzo[b]furanos funcionalizados.