Vinylogous Elimination/Heck Coupling/Allylation Domino Reactions: Access to 2‑Substituted 2,3-Dihydrobenzofurans and Indolines

A highly regio- and stereoselctive palladium-catalyzed domino reaction of functionalized aryl allyl ethers has been developed. Various aryl allyl ethers derived from the phosphine-catalyzed addition of electron-deficient allenes with phenol are found to be efficient substrates for the synthesis of 2-substituted 2,3-dihydrobenzofurans and indolines. It is the first example of aryl allyl ether used as an ideal and practical precursor of hard to get functionalized 1,3-butadiene for the heterocyclic compound synthesis.

本研究开发了一种具备高度区域选择性与立体选择性的钯催化官能化芳基烯丙基醚多米诺反应。研究表明，由缺电子联烯与苯酚经膦催化加成得到的多种芳基烯丙基醚，均可作为高效底物，用于合成2-取代的2,3-二氢苯并呋喃与吲哚啉类化合物。此为首例将芳基烯丙基醚作为难以制备的官能化1,3-丁二烯的理想实用前驱体，用于杂环化合物合成的研究案例。