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Literature DB >> 25531920

Metal-catalyzed thermal reactions of cyclic β-dicarbonyl phenyliodonium ylide with styrenes.

Alexandra-Eleni Bosnidou, Dimitra Kalpogiannaki, Sofia Karanestora, John A Nixas, Lazaros P Hadjiarapoglou.

Abstract

A cyclic β-dicarbonyl phenyliodonium ylide reacted with various substituted styrenes under Rh2(OAc)4 catalysis to give cyclopropanes and dihydrofurans in a highly regioselective fashion. When styrenes with electron-donating substituents or disubstituted were employed, only dihydrofurans were isolated instead. A mechanism involving two competing pathways rationalizes the results.

Entities: Chemical

Year: 2015 PMID： 25531920 DOI： 10.1021/jo502611x

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

1 in total

1. Non-decarbonylative photochemical versus thermal activation of Bu₄N[Fe(CO)₃(NO)] - the Fe-catalyzed Cloke-Wilson rearrangement of vinyl and arylcyclopropanes.

Authors: Che-Hung Lin; Dominik Pursley; Johannes E M N Klein; Johannes Teske; Jennifer A Allen; Fabian Rami; Andreas Köhn; Bernd Plietker
Journal: Chem Sci Date: 2015-09-03 Impact factor: 9.825

1 in total

Metal-catalyzed thermal reactions of cyclic β-dicarbonyl phenyliodonium ylide with styrenes.

1. Non-decarbonylative photochemical versus thermal activation of Bu4N[Fe(CO)3(NO)] - the Fe-catalyzed Cloke-Wilson rearrangement of vinyl and arylcyclopropanes.

1. Non-decarbonylative photochemical versus thermal activation of Bu₄N[Fe(CO)₃(NO)] - the Fe-catalyzed Cloke-Wilson rearrangement of vinyl and arylcyclopropanes.