Rhenium-Catalyzed Selective Synthesis of Polycyclicaromatic Compounds based on the Activation of Unsaturated Bond

从化学、生物活性分子和材料科学的角度来看，多取代芳香族化合物是一类很有吸引力的化合物。在这项研究中，我们研究了基于Re催化剂活化不饱和键的多种多取代芳香族化合物的选择性合成方法的发展。我们发现了三个新的反应：(I)由苯胺、醛和烯丙基硅烷处理得到的二亚胺与烯丙基硅烷反应合成喹啉类化合物；(Ii)由炔烃和邻炔取代苯甲醛反应选择性合成1，2-二取代萘；(Iii)由炔烃和苯乙醛等当量化合物选择性合成2，3-二取代萘。作为这些反应的应用，考察了各种含苯和萘邻苯衍生物的合成。

The polysubstituted aromatic compounds constituted an attractive class compounds from the view of chemical, biological active molecules and materials science. In this research, we have investigated the development of selective synthetic method of various multisubstituted aromatic compounds based on the activation of unsaturated bonds by rhenium catalyst.We now find three novel reactions, (i) the synthesis of quinolines by the reaction of aldimines, which were prepared by treatment of anilines and aldehydes, and allylic silanes, (ii) the selective synthesis of 1,2-disubstituted naphthalenes by the reaction of alkynes and o-alkynyl substituted benzaldehyde, and (iii) the selective synthesis of 2,3-disubstituted naphthalenes by the reaction of alkynes and phenylacetoaldehyde equivalents such styrene oxide or phenylacetoaldehyde dimethylacetal. As the application of these reactions, the synthesis of various orthophenylene derivatives bearing benzene and naphthalene was examined.