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Synfacts 2017; 13(03): 0253
DOI: 10.1055/s-0036-1590046
DOI: 10.1055/s-0036-1590046
Synthesis of Materials and Unnatural Products
Three Benzynes and the Ynolate
Umezu S.
dos Passos Gomes G.
Yoshinaga T.
Sakae M.
Matsumoto K.
Iwata T.
Alabugin I.
Shindo M.
* Florida State University, USA and Kyushu University, Kasuga, Japan
Regioselective One-Pot Synthesis of Triptycenes via Triple-Cycloadditions of Arynes to Ynolates.
Angew. Chem. Int. Ed. 2017;
56: 1298-1302
Regioselective One-Pot Synthesis of Triptycenes via Triple-Cycloadditions of Arynes to Ynolates.
Angew. Chem. Int. Ed. 2017;
56: 1298-1302
Further Information
Publication History
Publication Date:
15 February 2017 (online)
Significance
The triptycene structure is a remarkable scaffold that is frequently employed in functional materials as a result of its three dimensional, noncompliant structures and the interstitial space around the molecule. Most syntheses are based on a Diels–Alder cycloaddition between anthracene and an aryne. The authors describe a one-pot synthesis of triptycenes that proceeds through three cycloadditions of arynes to ynolates.
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Comment
The approach of formally inserting three arynes into an alkyne is a new and powerful way to obtain both simple and substituted triptycenes. Calculations provide an insight into the mechanism and explain the high regioselectivity (head-to-head-to-head).
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