Synthesis ( IF 2.6 ) Pub Date : 2017-12-11 , DOI: 10.1055/s-0036-1591846 Govindasamy Sekar , Selvaraj Chandrasekar , Iyyanar Karthikeyan
Dedicated to Prof. M. Periyasamy on the occasion of his 65th birthday.
Abstract
A highly efficient and base-controlled diastereoselective synthesis of tetraarylethanes through copper-catalyzed dehydrogenative homocoupling of readily available 2-benzylpyridines is reported. Various dl- and meso-tetraarylethanes were diastereoseletively synthesized by this new protocol, where base plays the role of the principle modulator: Grignard reagents selectively provide the C2 isomers, whereas KOt-Bu promotes the formation of the meso-tetraarylethanes. Interestingly, the presence of excess KOt-Bu generates the (E)-tetraarylethenes as the only product.
A highly efficient and base-controlled diastereoselective synthesis of tetraarylethanes through copper-catalyzed dehydrogenative homocoupling of readily available 2-benzylpyridines is reported. Various dl- and meso-tetraarylethanes were diastereoseletively synthesized by this new protocol, where base plays the role of the principle modulator: Grignard reagents selectively provide the C2 isomers, whereas KOt-Bu promotes the formation of the meso-tetraarylethanes. Interestingly, the presence of excess KOt-Bu generates the (E)-tetraarylethenes as the only product.
中文翻译:
铜催化的碱控制的非对映选择性从2-苄基吡啶合成四芳基乙烷的方法
专用于M. Periyasamy教授在他的65之际个生日。
抽象的
据报道,通过容易获得的2-苄基吡啶的铜催化的脱氢均偶联反应,可以高效地进行碱控制的非对映选择性合成四芳基乙烷。通过该新方案非对映体合成了各种dl-和内消旋-四芳基乙烷,其中碱起主要调节剂的作用:格氏试剂选择性地提供了C 2异构体,而KO t -Bu促进了内消旋-四芳基乙烷的形成。有趣的是,过量的KO t -Bu的存在产生了(E)-四芳基醚作为唯一产物。
据报道,通过容易获得的2-苄基吡啶的铜催化的脱氢均偶联反应,可以高效地进行碱控制的非对映选择性合成四芳基乙烷。通过该新方案非对映体合成了各种dl-和内消旋-四芳基乙烷,其中碱起主要调节剂的作用:格氏试剂选择性地提供了C 2异构体,而KO t -Bu促进了内消旋-四芳基乙烷的形成。有趣的是,过量的KO t -Bu的存在产生了(E)-四芳基醚作为唯一产物。