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Palladium-catalyzed tandem reaction of epoxynitriles with arylboronic acids in aqueous medium: divergent synthesis of furans and pyrroles

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Abstract

The efficient selective synthesis of furans and pyrroles has been realized by means of a palladium-catalyzed tandem addition/ring-opening/cyclization reaction of 2-(3-aryloxiran-2-yl)acetonitriles with arylboronic acids in aqueous medium for the first time. The chemoselectivity of this transformation can be predominantly governed by the steric effects of arylboronic acids: the reactions of 2-(3-aryloxiran-2-yl)acetonitriles with the less sterically hindered arylboronic acids provided furans as the sole products, while those of the sterically bulky arylboronic acids delivered pyrroles selectively. The 18O-labelled experiments revealed that the oxygen atom of furans is derived from water, and a plausible mechanism for this selective synthesis of furans and pyrroles was proposed.

Graphical abstract: Palladium-catalyzed tandem reaction of epoxynitriles with arylboronic acids in aqueous medium: divergent synthesis of furans and pyrroles

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Article information


Submitted
23 Aug 2020
Accepted
20 Sep 2020
First published
22 Sep 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Palladium-catalyzed tandem reaction of epoxynitriles with arylboronic acids in aqueous medium: divergent synthesis of furans and pyrroles

S. Yu, L. Dai, Y. Shao, R. Li, Z. Chen, N. Lv and J. Chen, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO01016B

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