Chemistry - A European Journal
Chemistry - A European Journal
5 years ago

Double Gold Activation of 1-Ethynyl-2-(Phenylethynyl)benzene Toward 5-exo-dig and 6-endo-dig Cyclization Reactions

Double Gold Activation of 1-Ethynyl-2-(Phenylethynyl)benzene Toward 5-exo-dig and 6-endo-dig Cyclization Reactions
A. Stephen K. Hashmi, Alejandro Toro-Labbé, Soledad Gutiérrez-Oliva, Mie Højer Vilhelmsen, Nery Villegas-Escobar
In the dual gold catalytic conversion of 1-ethynyl-2-(phenylethynyl)benzene to yield dibenzopentalene, a 5-exo-dig competes with a 6-endo-dig cyclization by formation of a five- and six-membered ring, respectively. This stage is rather important since it is the selectivity-determining step. The crucial competition between the formation of the five and six-membered rings finishes either with the completeness of the catalytic cycle toward dibenzopentalene or by formation of an aryl intermediate, which stabilizes as 2-phenyl-naphthalene. More information can be found in the Full Paper by A. S. K. Hashmi, A. Toro-Labbé et al. (DOI: 10.1002/chem.201701595).

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201703131

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