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
a  Università 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
,
Matteo Lanzi
a  Università 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
,
Gianpiero Cera
a  Università 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
,
b  UPMC Sorbonne Université, IPCM (UMR CNRS 8232), 4 place Jussieu, C. 229, 75005 Paris, France   Email: max.malacria@upmc.fr
,
a  Università 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
› Author Affiliations
Research on metal aromaticity was supported by Ministero dell’Istruzione, dell’Università e della Ricerca (MIUR; grant AROMA-TriP and Departments of Excellence framework).
Further Information

Publication History

Received: 30 November 2018

Accepted: 18 December 2018

Publication Date:
18 January 2019 (online)


Published as part of the 50 Years SYNTHESISGolden 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.

Supporting Information

 
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