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A Facile Route to Bridgehead Disubstituted Bicyclo[1.1.1]pentanes Involving Palladium‐Catalyzed Cross‐Coupling Reactions
Author(s) -
Daniel Rehm J. D.,
Ziemer Burghard,
Szeimies Günter
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199909)1999:9<2079::aid-ejoc2079>3.0.co;2-d
Subject(s) - chemistry , palladium , catalysis , diethyl ether , reagent , bicyclic molecule , solvent , coupling (piping) , ether , coupling reaction , medicinal chemistry , combinatorial chemistry , organic chemistry , mechanical engineering , engineering
3‐Alkylbicyclo[1.1.1]pent‐1‐yl Grignard reagents have been coupled with bromoarenes in the presence of catalytic amounts (0.8–2.0 mol.%) of PdCl 2 (dppf) in diethyl ether containing 1,4‐dioxane as a co‐solvent at room temperature. The yields of the coupling step range from 73% to 98%. By using di‐ or tribromoarenes, coupling products of types 10 and 11 have been obtained. The X‐ray structures of four model compounds ( 4a , 4d , 4j , 4n ) have been determined, each of which shows a short, nonbonded C1–C3 distance in the bicyclo[1.1.1]pentyl subunit of about 1.89 Å.