Rhodium(I)-catalyzed decarbonylative spirocyclization through C-C bond cleavage of benzocyclobutenones: an efficient approach to functionalized spirocycles.
The rhodium-catalyzed formation of all-carbon spirocenters involves a decarbonylative coupling of trisubstituted cyclic olefins and benzocyclobutenones through CC activation. The metal-ligand combination [{Rh(CO)2 Cl}2 ]/P(C6 F5 )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.
Department of Chemistry, University of Texas at Austin, 100 east 24th street, Austin, TX 78712 (USA) http://gbdong.cm.utexas.edu/
Tao
T
Xu
Nikolas A
NA
Savage
Guangbin
G
Dong
D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D011083:Polycyclic Compounds; D013141:Spiro Compounds; C079040:benzocyclobutene; D012238:Rhodium
CC activation; decarbonylation; homogeneous catalysis; rhodium; spirocycles