利用鈀金屬催化與碳氫鍵活化鄰苯基苯胺與鄰苯基苯酚合成具生物活性的菲啶酮與苯并吡喃酮衍生物

Abstract

本篇論文主要是利用鈀金屬催化，使用Pd(OAc)2當作催化劑，將鄰苯基苯胺與鄰苯基苯酚反應物的碳氫鍵活化，進一步與一氧化碳進行插入反應，最後環化生成具生物活性的菲啶酮(phananthridinones)與苯并吡喃酮(benzopyranones)衍生物。本文將會探討最佳化反應條件，接著更換起始物上的取代基去進行反應，探討其推拉電子效應對反應性的影響。之後進行光譜分析，其中從碳譜中化學位移為160 ppm左右的羰基訊號，可以判斷出是否成功獲得羰基化產物，另外也利用X光單晶繞射獲得該化合物結構。

In this thesis, we investigated palladium-catalyzed oxidative carbonylation of N-sulfonyl-2-aminobiaryls through C–H bond activation and C–C, C–N bond formation under milder conditions to synthesize bioactive phenanthridinone derivatives in one pot, and we also applied the method of palladium-catalyzed oxidative carbonylation to 2-aryphenols via one O–H and C–H bond cleavage and one new C–C and C–O bond formation under similar conditions. Both reactions tolerated a variety of substrates and provided biologically important phenanthridinone and benzopyranone derivatives with moderate to excellent yields. In this study, we also optimized the reaction conditions and discussed the reactivity of different functional groups as starting materials. NMR, IR, MS and X-ray diffraction techniques were used to characterize these carbonylation derivatives.