利用Pd(dba)2催化丙二烯（(CH3)2CCCH2），芳香基鹵化物（aryl halide, ArX）與有機硼試劑（Ar'B(OH)2）進行三組成偶合反應(three-component coupling reaction)，可得到三組成產物 （(CH3)2CC(Ar)Ar'）、1,3-丁二烯衍生物（CH3(CH2)CC(CH2)Ar）、Suzuki偶合 (Ar-Ar')三種產物；我們分別嘗試不同的反應條件；在70℃以DMF為溶劑CsF為鹼，沒有配位子的存在下反應7小時，可得到產率最高的三組成產物。
此外，利用不同的單一取代丙二烯類(R(H)CCCH2)，如：cyclopentyl、cyclohexyl、t-butyl、n-butyl取代，反應亦可進行。反應中所形成的丙烯基鈀金屬錯合物中間體(p-allyl palladium)會因取代基的立體障礙影響使得產物有不同比例E、Z形式兩種組態；而其E/Z比率介在97%~73%之間。

在改變芳香基鹵化物(ArX)的部份，芳香環上取代基無論是推電子基或拉電子基對產率的效應並不明顯，但若使用立體障礙較大的鄰位取代產率會比立體障礙較小的間位或對位取代低；而以醯氯化物（acid chloride, ArCOCl）代替芳香基鹵化物在類似的反應條件下，反應不會進行。在改變有機硼試劑(Ar'B(OH)2)的部份，芳香環上之取代基的推、拉電子基對產率的效應亦不明顯，但若使用立體障礙較大的鄰位取代產率會比立體障礙較小的間位或對位取代低。

分子內環化反應部份，我們引進了o-IC6H4O(H)CCCH2 (1f)及o-IC6H4CH2O(H)CCCH2 (1g)為起始物，可以成功的利用鈀金屬催化進行偶合反應，得到產率相當不錯的五環及六環產物，而不同的有機硼試劑(Ar'B(OH)2)對反應結果並無太大效應。我們並綜合以上的訊息，提出了可能的反應機構。

We previously reported the palladium-catalyzed cross-coupling reactions of orangodiboronates with acyl chlorides R1COCl, allenes R2R3CCCH2 to give an allylboronates R2R3CC(R1)B(OCCH3)2, which is one carbon-carbon bond formation. In this study, we wish to reporte the synthesis of two carbon-carbon bond formation via the palladium-catalyzed three-component coupling of allenes RR'CCCH2, arylboronic acids ArB(OH)2 and aromatic halides Ar'X. We also use 2-iodobenzyloxyallene as the starting material to get cyclization product ioschromene. Based on known palladium-allene and -allyl chemistry, we propose a mechanism to account for this palladium-catalyzed three-component coupling reactions.

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