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Synlett 2020; 31(09): 829-837
DOI: 10.1055/s-0039-1690779
DOI: 10.1055/s-0039-1690779
synpacts
Epoxides as Dual-Functionalized Alkylating Reagents in Catellani Reactions for the Assembly of Heterocycles
We are grateful to the National 1000-Youth Talents Plan, the Innovation Team Program of Wuhan University (Program No. 2042017kf0232), start-up funding from Wuhan University, National Natural Science Foundation of China (Grants 21871213, and 21801193), and the China Postdoctoral Science Foundation (No. 2016M602339, H.G.C.) for financial support.Further Information
Publication History
Received: 05 November 2019
Accepted after revision: 05 December 2019
Publication Date:
02 January 2020 (online)
Abstract
Reported is a cooperative catalytic system consisting of a complex of Pd with dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (XPhos) and the potassium salt of 5-norbornene-2-carboxylic acid that permits the use of epoxides as dual-functionalized alkylating reagents in Catellani-type reactions for the assembly of heterocycles. Salient features of this research include readily available substrates, use of the potassium salt of 5-norbornene-2-carboxylic acid as a catalytic mediator as well as a base, and excellent regioselectivity for the cleavage of epoxides. This mild, chemoselective, scalable, atom- and step-economic protocol offers a straightforward approach for the assembly of isochroman and 2,3-dihydrobenzofuran scaffolds.
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For related reviews, see:
For mechanistic studies on Catellani-type reactions, see:
For selected examples, see:
For selected examples, see:
For selected reviews, see:
For recent reviews, see: