An Efficient Route to 2,6-Disubstituted Styrenes via the Palladium-Catalyzed [4 + 2] Cyclodimerization of Conjugated Enynes
- 12 September 1998
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 63 (20) , 7022-7025
- https://doi.org/10.1021/jo980967+
Abstract
An efficient and general method for the synthesis of 2,6-disubstituted styrenes 5 via the palladium-catalyzed [4+2] homobenzannulation of conjugated enynes 4 was developed. In all cases, the reactions proceeded in regiospecific manner, affording the disubstituted styrenes, bearing various functional groups at the 2 and 6 positions of the benzene ring, as a single reaction product in good to excellent yields. Initial attempts at cross-cycloaddition of two different enynes indicated low degrees of chemoselectivity of this process. Accordingly, the cross-dimerization products 6 in all cases were accompanied with notable amounts of the chemoisomeric homodimers 5.Keywords
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