Rhodium(I)‐Catalyzed Decarbonylative Spirocyclization through CC Bond Cleavage of Benzocyclobutenones: An Efficient Approach to Functionalized Spirocycles

Tao Xu, Nikolas A. Savage, Guangbin Dong

Angewandte Chemie · 2014 · 30 citations · 37 references

Concepts

Abstract

Abstract 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(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.

References

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