Laboratório de Síntese, Reatividade, Avaliação Farmacológica e Toxicológica de Organocalcogênios, CCNE, UFSM, Santa Maria, Rio Grande do Sul, Brazil 97105-900.
J Org Chem. 2009 Mar 6;74(5):2153-62. doi: 10.1021/jo802736e.
An efficient synthesis of 2-chalcogen-3-substituted-benzo[b]furan compounds has been accomplished via electrophilic cyclization reaction of 2-chalcogenealkynyl anisoles using I(2), ICl, Br(2), and PhSeBr as electrophile sources. The product distributions were strongly dependent on the nature of substituents in the aromatic ring of anisole and on the chalcogen atom directly bonded to the triple bond. The 2-chalcogen-3-iodo-benzo[b]furans obtained smoothly underwent conversion to more complex structures of benzo[b]furan derivatives via palladium- or copper-catalyzed cross-coupling reaction with thiols, diphenyl diselenides, and zincates.
通过使用 I(2)、ICl、Br(2)和 PhSeBr 作为亲电试剂源，对 2-杂原子炔基苯甲醚进行亲电环化反应，高效合成了 2-杂原子-3-取代苯并[b]呋喃化合物。产物分布强烈依赖于苯甲醚芳环上取代基的性质和直接与三键键合的杂原子。通过钯或铜催化与硫醇、二苯二硒醚和锌盐的交叉偶联反应，2-杂原子-3-碘苯并[b]呋喃可以顺利转化为更复杂的苯并[b]呋喃衍生物结构。
