本碩士論文之目標在於發展新的合成方法，製備9-芳烴茀 (10)的相關衍生物，以期用於有機發光二極體與掌性催化劑中。初步測試的結果顯示，由醋酸鈀與三環己基磷組成的系統，對於茀 (2) 與苯鹵化物 (25) 生成9-芳烴茀 (10) 的反應具有不錯的催化效果。此耦合反應的限制性及相關細節已被仔細地探討。各式官能基包括烷基、烷氧基、酯基、酮基與氰基等，均可被導入所設計化合物內。此外，此方法亦可用於9,9-雙芳烴茀 (11) 及四芳烴茚茀 (32) 的製備。
探討反應條件時，發現鈀金屬催化劑、配位基、鹼與溶劑在反應中均扮演重要的角色。反應條件已最適化:將茀 (2)、 2-溴甲苯 (25c)、醋酸鈀、三環己基磷四氟硼酸鹽及碳酸鍶溶解於N.N-二甲基乙醯胺內，置於厚壁封管中，經氮氣除氧五分鐘後，在130 ºC下反應約12小時可得到94 的9-(2-苄基)茀 (10c)。多種具備不同官能基的芳烴茀衍生物 (10, 11)，均可在此系統中被合成出。相較於傳統方法，本論文的合成策略不僅效率佳且操作便利，相信是未來重要的研究工具之一。

The main goal of this paper is to develop a new synthetic method for the preparation of 9-arylfluorene (10), which is applicable to OLEDs and chiral catalysts. In the presence of a catalytic system comprised of palladium(II) acetate and tris(cyclohexyl)phosphonium tetrafluoroborate, the reaction of fluorene (2) with haloarenes (25) generated 9-arylfluorenes (10) in good to excellent yields. The scope and limitations of the coupling reaction were investigated. A wide range of functional groups, including alkyl, alkoxy, ester, ketone and nitrile can tolerate the reaction conditions. Furthermore, this synthetic method is also utilized to prepare 9,9-diarylfluorenes (11) and tetraarylindenofluorene (32).
Systematic studies of reaction conditions revealed that palladium catalysts, ligands, bases and solvents all play key roles. The reaction conditions have been optimized. A mixture of fluorene (2), 2-bromotoluene (25c), Pd(OAc)2, PCy3•HBF4, Cs2CO3 and N,N-Dimethylacetamide in a thick-walled Pyrex tube was purged with nitrogen for 5 min. The sealed tube was kept in an oil bath at 130 ºC for 12 hours. 9-(2-toluenyl)fluorene (10c) could be obtained in 94 yield. Several arylfluorene derivatives (10, 11) with different functional groups have been generated in this system. Compared with traditional methods, this synthetic protocol is more efficient and convenient.

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