Synthesis of 9,10-Diarylanthracenes via Mg(TMP)2·2LiCl-Mediated Benzyne Generation/[4+2] Cycloaddition and Deoxygenation of 9,10-Epoxyanthracene Intermediates
作者:Hidetoshi Tokuyama、Naoya Miyamoto、Yuki Nakazawa、Takanori Nakamura、Kentaro Okano、Sota Sato、Zhe Sun、Hiroyuki Isobe
DOI:10.1055/s-0036-1591510
日期:2018.3
route to functionalized 9,10-diarylanthracenes has been developed. 9,10-Epoxyanthracene intermediates were prepared by [4+2] cycloaddition of 1,3-diarylisobenzofuran with a variety of functionalized benzyne intermediates, which were obtained by Mg(TMP)2·2LiCl-mediated benzyne generation. For the cleavage of the resultant 9,10-epoxyanthracene intermediates, we developed mild deoxygenation conditions
已开发出功能化 9,10-二芳基蒽的新合成路线。9,10-环氧蒽中间体是通过 1,3-二芳基异苯并呋喃与多种功能化的苄中间体的 [4+2] 环加成反应制备的,这些中间体是通过 Mg(TMP)2·2LiCl 介导的苄生成获得的。为了裂解得到的 9,10-环氧蒽中间体,我们使用三氟乙酸和 Et3SiH 的组合开发了温和的脱氧条件。通过应用于 5,7,12,14-四苯基并五苯的合成证明了该序列的效用。