利用鎳金屬催化進行芳基碘到腈上的分子間插入反應

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Title:	利用鎳金屬催化進行芳基碘到腈上的分子間插入反應
Other Titles:	Nickel-catalyzed intermolecular insertion of aryl iodides to nitriles
Authors:	陳彥中;Chen, Yen-Chung
Contributors:	淡江大學化學學系碩士班謝仁傑;Hsieh, Jen-Chieh
Keywords:	鎳金屬;芳基碘;芳香酮;Nickel;aryl iodides;aryl ketones
Date:	2012
Issue Date:	2013-04-13 11:04:37 (UTC+8)
Abstract:	我們成功的發展出第一個使用第一行後期過渡金屬鎳來進行芳基碘到腈上的分子間插入反應。一開始改變各種反應條件並觀察其對於反應之影響，得到了最佳化的反應條件為：0.5 mmol (1當量)芳香碘(a)，1.0 mmol 有機腈化合物(b)，10 mol % NiCl2(DME)，10 mol % 1,3-雙(二苯基磷)丙烷(dppp)，2當量鋅粉和1.2當量的水溶於0.3毫升的乙二醇二甲醚(DME)在攝氏100度下反應24小時。使用此最佳化條件，我們分別改變芳基碘(a)和有機腈化合物(b)上的取代基來探討立體效應和電子效應對於反應的影響，最後推測本反應的反應機構。利用NiCl2(DME)/dppp/Zn系統催化，不同以往使用較為昂貴難取得的芳香硼酸化合物，使用較便宜的芳基碘來進行分子間插入到腈上的反應，並能容忍各種官能基的影響，成功得到多取代的芳香酮類衍生物及色酮類天然化合物1。 We have developed a novel methodology for the intermolecular insertion of aryl iodides to nitriles catalyzed by a nickel complex.Up to now, there has been no example of using firstrow transition metal complexes as catalyst for the addition of aryl iododes to nitriles.This is the first report that nitriles can undergo intermolecular insertion with aryl iodides to furnish various arylketone derivatives in moderate to excellent yields with tolerance of a very wide variety of functional groups. Further studies to explore the possibility for the synthesis of various chromones as well as to extend the application of this catalytic system are currently underway.
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