1,1-二溴-2-取代苯基乙烯在环化反应中的应用

Application of 1,1-Dibromo-2-Arylalkene in Cyclization Reaction

1,1-二溴-2-取代苯基乙烯是一种重要的有机合成中间体,该类化合物可以以芳醛为原料,通过Corey-Fuch法简便制备,并广泛应用于多取代烯烃、(E)-1-溴-2-取代苯基乙烯、芳炔、1,3-二炔(多炔)、芳炔溴化物和炔胺等化合物的合成。1,1-二溴-2-取代苯基乙烯中的(E)-Br和(Z)-Br存在明显的反应活性差异,因而适合于设计各种串联反应路线。近年来,利用其(E)-Br参与的Stille反应,Heck反应,Suzuki-Miyaura反应,Buchwald-Hartwig等各种偶联反应以及(Z)-Br和取代苯基邻位各种活性反应基团之间的环化反应,以1,1-二溴-2-取代苯基乙烯衍生物为底物合成了异香豆素类、茚类、吲哚类、异吲哚类、苯并噻吩和苯并呋喃类等多种具有重要生理活性或有合成价值的稠(杂)环化合物。本文从合成的化合物类别角度出发,对该领域近年来的研究进展进行了回顾和展望。

1,1-Dibromo-2-arylalkenes,a kind of important organic intermediates,which are easily prepared from aryl aldehydes by Corey and Fuchs＇ procedure,have been found wide applications in the synthesis of polysubstituted alkenes,（E）-arylvinyl bromides,arynes,1,3-diynes,polyynes,1-bromo-1-alkynes and ynamines.Due to the difference of reactive activity between（E）-Br and（Z）-Br,1,1-dibromo-2-arylalkenes are fit for designing tandem reaction.In recent years,various fused ring compounds and heterocyclic compounds bearing potential biological activities and synthetic value including isocoumarin,indene,indole,isoindole,benzothiophene and benzofuran,etc.were synthesized through 1,1-dibromo-2-arylalkenes based on Stille reaction,Heck reaction,Suzuki-Miyaura reaction,Buchwald-Hartwig reaction,etc.involving the（E）-Br and cyclization between the（E）-Br and the active group at the para-position of the aryl ring.In this paper,the application of 1,1-dibromo-2-arylalkenes on cyclization reaction in the past decade is surveyed.