A selective removal of the secondary hydroxy group from <i>ortho</i>-dithioacetal-substituted diarylmethanols
作者:Anna Czarnecka、Emilia Kowalska、Agnieszka Bodzioch、Joanna Skalik、Marek Koprowski、Krzysztof Owsianik、Piotr Bałczewski
DOI:10.3762/bjoc.14.105
日期:——
ortho-1,3-dithianylaryl(aryl)methanols which enables a selective removal of the secondary hydroxy group in presence of the 1,3-dithianyl moiety under reductive conditions. This reaction proceeds well with ZnI2/Na(CN)BH3 in dichloroethane or benzene for both unsubstituted and substituted aryls (by electron-rich groups). This is leading to formyl-protected diarylmethanes with potential application in the
我们提出了邻-1,3-二噻吩基芳基(芳基)甲醇的成功脱氧反应,该反应能够在还原条件下在存在1,3-二噻吩基部分的情况下选择性除去仲羟基。对于未取代的和取代的芳基(通过富电子基团)的二氯乙烷或苯中的ZnI2 / Na(CN)BH3,该反应进展顺利。这导致了甲酰基保护的二芳基甲烷在新药物和光电子材料合成中的潜在应用。这种合成方法可以以26%至95%的产率获得各种功能化的邻-1,3-二硫基芳基(芳基)甲烷,推荐用于含硫原子的底物,而过渡金属引发的反应会失败。