Li Bin, Shen Nana, Yang Yujie, Zhang Xinying, Fan Xuesen
School of Environment, School of Chemistry and Chemical Engineering, Key Laboratory for Yellow River and Huai River Water Environmental Pollution Control and Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Key Laboratory of Organic Functional Molecules and Drug Innovation, Collaborative Innovation Center of Henan Province for GreenManufacturing of Fine Chemicals, Henan Normal University, Xinxiang, Henan 453007, China.
Org Lett. 2021 Jan 15;23(2):388-393. doi: 10.1021/acs.orglett.0c03882. Epub 2020 Dec 29.
An efficient synthesis of indeno[1,2-]furan and 3-benzoylindenone derivatives through a FeCl-catalyzed carbene/alkyne metathesis reaction of -alkynylbenzoyl diazoacetates is presented. Mechanistically, the key intermediate, vinyl iron carbene, is formed by 5 carbocyclization and terminated with a formal [3 + 2] cycloaddition or carbonylation. To the best of our knowledge, this is the first example in which FeCl is used as a catalyst for a carbene/alkyne metathesis reaction. Finally, derivatization reactions were carried out to showcase the value of the products.
本文报道了通过FeCl催化的α-炔基苯甲酰基重氮乙酸酯的卡宾/炔烃复分解反应高效合成茚并[1,2 -]呋喃和3-苯甲酰基茚酮衍生物。从机理上讲，关键中间体乙烯基铁卡宾是通过5-碳环化形成的，并以形式上的[3 + 2]环加成或羰基化终止。据我们所知，这是首次将FeCl用作卡宾/炔烃复分解反应催化剂的实例。最后，进行了衍生化反应以展示产物的价值。
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