Complementary Reactivity of 1,6-Enynes with All-Metal Aromatic Trinuclear Complexes and Carboxylic Acids

Chiara Cecchini; Matteo Lanzi; Gianpiero Cera; Max Malacria; Giovanni Maestri

doi:10.1055/s-0037-1611653

Synthesis, Table of Contents

CC BY-ND-NC 4.0 · Synthesis 2019; 51(05): 1216-1224
DOI: 10.1055/s-0037-1611653

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Complementary Reactivity of 1,6-Enynes with All-Metal Aromatic Trinuclear Complexes and Carboxylic Acids

Chiara Cecchini

^aUniversità di Parma, Dipartimento di Scienze Chimiche, della Vita e della Sostenibilità Ambientale, 17/A Parco Area delle Scienze, 43124 Parma, Italy Email: giovanni.maestri@unipr.it

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Matteo Lanzi

^aUniversità di Parma, Dipartimento di Scienze Chimiche, della Vita e della Sostenibilità Ambientale, 17/A Parco Area delle Scienze, 43124 Parma, Italy Email: giovanni.maestri@unipr.it

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Gianpiero Cera

^aUniversità di Parma, Dipartimento di Scienze Chimiche, della Vita e della Sostenibilità Ambientale, 17/A Parco Area delle Scienze, 43124 Parma, Italy Email: giovanni.maestri@unipr.it

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Max Malacria *

^bUPMC Sorbonne Université, IPCM (UMR CNRS 8232), 4 place Jussieu, C. 229, 75005 Paris, France Email: max.malacria@upmc.fr

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Giovanni Maestri *

^aUniversità di Parma, Dipartimento di Scienze Chimiche, della Vita e della Sostenibilità Ambientale, 17/A Parco Area delle Scienze, 43124 Parma, Italy Email: giovanni.maestri@unipr.it

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Abstract

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Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue

Abstract

The distinct reactivity of 1,6-enynes in the presence of a trinuclear metal complex activated by a carboxylic acid is presented. The triplatinum catalyst enables the cyclization of the substrate and subsequent incorporation of a nucleophile in the final product. In contrast, sequential cyclization/double bond shift occurs under analogous conditions in the presence of the corresponding tripalladium complex.

Key words

enynes - palladium - platinum - clusters - aromaticity - cyclization

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