The Rearrangement of <i>tert</i>-Butylperoxides for the Construction of Polysubstituted Furans
作者:Xiaojian Zheng、Shenglin Lu、Zhiping Li
DOI:10.1021/ol402509u
日期:2013.11
The Brønsted acid catalyzed rearrangement of tert-butyl peroxides provides a new strategy to construct 2,3-disubstituted furans via 1,2-aryl migration. In addition, tert-butyl peroxides could also be transformed into 2,3,5-trisubstituted or 2,5-disubstitutedfuransthrough a sequence of base-catalyzed Kornblum–DelaMare rearrangements and acid-promoted Paal–Knorr reactions.
A convenient and straightforward strategy for the synthesis of 2,3-disubstituted and 2,3,5-trisubstituted furans via a base-promoted domino reaction of β-keto compounds with vinyl dichlorides is described. This transition-metal-free approach proceeds under operationally simple reaction conditions featuring easily available starting materials, a broad substrate scope, and good functional group tolerance
In the presence of tert-butyl peroxide (TBHP), the copper-catalyzed annulation of 1,3-dicarbonyl compound with diethylene glycol was developed leading to 2,3-disubstituted furan. Diethylene glycol serves as a cheap and environmentally friendly equivalent of ethyne, with the release of H2O and alcohol as clean wastes The procedure involves a sequential O- and C-functionalization of beta-ketoester by diethylene glycol.