鎳金屬催化benzoxazole與1,5-cyclooctadiene的偶合反應時，可以調整磷基團或碳烯的配位基，分別得到烷基化產物與烯基化產物。其中，烷基化產物其雙鍵位置在環上的2號位置，與我們預期中的4號位置不同。另外在反應中生成烯基化產物，是非常特別的現象，因為在此反應條件中，必須還要另外加入氧化劑才會生成烯基化產物，但我們使用的反應條件並沒有包含氧化劑，於是我們便針對烯基化產物進行研究也成功找出烯基化反應的最佳條件，發現可能是當作溶劑的1,5-cyclooctadiene同時扮演氧化劑的角色。我們也將此方法應用在各種不同的芳香雜環進行烯基化反應，也都可以順利得到高選擇性的烯基化產物。我們推測造成預期的烷基化產物與實際得到的烷基化產物不同以及形成烯基化產物的原因，應該是受異構化反應影響，所以我們在反應機制探討中，進行異構化反應測試，並推測出可能的反應機制。

Nickel-phosphine and NHC catalysts have been developed for the cross coupling reaction of benzoxazole and 1,5-cyclooctadiene to afford alkylation and alkenylation products in high regioselectivity. To our surprise, the double bond position of the alkylation product was occurred at C2 position, which was different from our expectation product at C4 position. Furthermore, it was attractive nickel mediated method to afford Heck-type alkenylation product without using an external oxidant. Yet, one of unsaturated moiety in 1,5-cyclooctadiene was sacrificed as a proton acceptor. Various heteroarenes reacted smoothly with 1,5-cyclooctadiene to produce alkenylation products in good to excellent yield with high regioselectivity. We speculated that the shift of double bond in the alkylation products and the formation of the alkenylation were caused by the isomerization process. Therefore, based on literature precedents and experiments about isomerization, we proposed the plausible mechanisms for alkylation and alkenylation.

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