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Rhodium(I)‐Catalyzed Decarbonylative Spirocyclization through CC Bond Cleavage of Benzocyclobutenones: An Efficient Approach to Functionalized Spirocycles
Author(s) -
Xu Tao,
Savage Nikolas A.,
Dong Guangbin
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201310149
Subject(s) - decarbonylation , rhodium , catalysis , chemistry , cleavage (geology) , bond cleavage , ligand (biochemistry) , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , materials science , biochemistry , receptor , fracture (geology) , composite material
The rhodium‐catalyzed formation of all‐carbon spirocenters involves a decarbonylative coupling of trisubstituted cyclic olefins and benzocyclobutenones through CC activation. The metal–ligand combination [{Rh(CO) 2 Cl} 2 ]/P(C 6 F 5 ) 3 catalyzed this transformation most efficiently. A range of diverse spirocycles were synthesized in good to excellent yields and many sensitive functional groups were tolerated. A mechanistic study supports a hydrogen‐transfer process that occurs through a β‐H elimination/decarbonylation pathway.