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A Facile Route to Bridgehead Disubstituted Bicyclo[1.1.1]pentanes Involving Palladium-Catalyzed Cross-Coupling Reactions

✍ Scribed by J. D. Daniel Rehm; Burghard Ziemer; Günter Szeimies

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
194 KB
Volume
1999
Category
Article
ISSN
1434-193X

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✦ Synopsis

3-Alkylbicyclo[1.1.1]pent-1-yl Grignard reagents have been using di-or tribromoarenes, coupling products of types 10 and 11 have been obtained. The X-ray structures of four coupled with bromoarenes in the presence of catalytic amounts (0.8-2.0 mol.%) of PdCl 2 (dppf) in diethyl ether model compounds (4a, 4d, 4j, 4n) have been determined, each of which shows a short, nonbonded C1-C3 distance in containing 1,4-dioxane as a co-solvent at room temperature. The yields of the coupling step range from 73% to 98%. By the bicyclo[1.1.1]pentyl subunit of about 1.89 A ˚.

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