可调控的1,2,3,4,5-五芳基取代吡咯的合成研究

Study on the Synthesis Design of 1,2,3,4,5-all Aryl Substituted Pyrrole

五芳基吡咯的应用十分广泛,如化学检测、生物传感、细胞成像等。已报道五芳基吡咯的合成主要通过分子间的环化反应实现,由于存在区域选择性而受限于对称的底物,难以得到完全不同取代的五芳基吡咯。以烯胺酮为底物,利用课题组开发的分子内缩合反应,在超碱体系下首先合成不同取代的1,2,3,5-四芳基吡咯;随后利用4-位溴化和Suzuki反应,完成不同取代的1,2,3,4,5-五芳基吡咯的合成。为1,2,3,4,5-五芳基吡咯的可调控合成提供一种简便合成方法,有望应用于有机光电材料的开发。

Pentaryl pyrroles have a wide range of applications,including chemical detection,biosensing,and cell imaging.The reported synthesis of pentaryl pyrroles is primarily achieved through intermolecular cyclization reactions,but regioselectivity limitations restrict the process to symmetrical substrates,making it difficult to obtain fully substituted pentaryl pyrroles.In this work,we used enaminones as substrates and employed an intramolecular condensation reaction developed by our group to synthesize various substituted 1,2,3,5-tetraaryl pyrroles under a superbase system.Subsequently,through bromination at the 4-position and a Suzuki reaction,we successfully synthesized various substituted 1,2,3,4,5-pentaryl pyrroles.This study provides a simple method for the tunable synthesis of 1,2,3,4,5-pentaryl pyrroles,with potential applications in the development of organic optoelectronic materials.