Synfacts 2017; 13(03): 0253
DOI: 10.1055/s-0036-1590046
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Three Benzynes and the Ynolate

Timothy M. Swager
Constantin-Christian A. Voll
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
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15. Februar 2017 (online)



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.



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).