Epoxides as Dual-Functionalized Alkylating Reagents in Catellani Reactions for the Assembly of Heterocycles

Chenggui Wu; Hong-Gang Cheng; Qianghui Zhou

doi:10.1055/s-0039-1690779

Synlett, Inhaltsverzeichnis

Synlett 2020; 31(09): 829-837
DOI: 10.1055/s-0039-1690779

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Epoxides as Dual-Functionalized Alkylating Reagents in Catellani Reactions for the Assembly of Heterocycles

Chenggui Wu

^aSauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds and Materials (Ministry of Education), College of Chemistry and Molecular Sciences, Wuhan University, 430072 Wuhan, P. R. of China eMail: hgcheng@whu.edu.cn

,

Hong-Gang Cheng∗

^aSauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds and Materials (Ministry of Education), College of Chemistry and Molecular Sciences, Wuhan University, 430072 Wuhan, P. R. of China eMail: hgcheng@whu.edu.cn

,

Qianghui Zhou∗

^aSauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds and Materials (Ministry of Education), College of Chemistry and Molecular Sciences, Wuhan University, 430072 Wuhan, P. R. of China eMail: hgcheng@whu.edu.cn

^bThe Institute for Advanced Studies, Wuhan University, 430072 Wuhan, P. R. of China eMail: qhzhou@whu.edu.cn

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Abstract

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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.

Key words

Catellani reaction - cooperative catalysis - epoxides - isochromans - dihydrobenzofurans

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Referenzen

References and Notes
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