Álvarez Estela, Nieto Faza Olalla, Silva López Carlos, Fernández-Rodríguez Manuel A, Sanz Roberto
Área de Química Orgánica, Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Pza. Misael Bañuelos s/n, 09001-Burgos (Spain).
Departamento de Química Orgánica, Universidade de Vigo, Lagoas Marcosende, 36310-Vigo, Galicia (Spain).
Chemistry. 2015 Sep 7;21(37):12889-93. doi: 10.1002/chem.201502174. Epub 2015 Jul 24.
A cascade reaction of indoles with propargylic diols involving an unprecedented metal-free 1,2-indole migration onto an alkyne was carried out. DFT calculations support a mechanism consisting of a concerted nucleophilic attack of the indole nucleus with loss of water, followed by the 1,2-migration and subsequent Nazarov cyclization. This Brønsted acid-catalyzed protocol affords indole-functionalized benzofulvene derivatives in high yields.
进行了吲哚与炔丙二醇的串联反应，该反应涉及前所未有的无金属1,2-吲哚迁移至炔烃上。密度泛函理论计算支持一种机理，该机理包括吲哚核的协同亲核进攻并伴随水的失去，随后是1,2-迁移以及随后的纳扎罗夫环化反应。这种布朗斯特酸催化的方法能以高产率得到吲哚官能化的苯并富烯衍生物。
