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Iron(III)-Catalyzed Domino Claisen Rearrangement/Regio- and Chemoselective Aerobic Dehydrogenative Cyclization of β-Naphthyl-Substituted-Allenylmethyl Ether

Author:
Zhang, Chenyun, Zhen, Long, Yao, Zhi, Jiang, Liqin
Source:
Organic letters 2019 v.21 no.4 pp. 955-959
ISSN:
1523-7052
Subject:
catalysts, chemical structure, chemoselectivity, dehydrogenation, ferric chloride, furans
Abstract:
An FeCl₃-catalyzed allenic Claisen rearrangement/regio- and chemoselective aerobic dehydrogenative cyclization domino reaction is developed, providing a wide range of 2-aryl/alkyl, 3-(substituted-vinyl)naphtho[2,1-b]furans in high yields at 95–130 °C in an atom- and step-economic fashion. Mechanistic studies suggest that the FeCl₃ catalyst is responsible for the high regio- and chemoselectivity in reaction. A blue-emitting product shows quantum yield of 0.95. The reaction proceeds readily on the gram scale, and synthetic applications of the products are also demonstrated.
Agid:
6310473