tert-Butoxide-Mediated Protodeformylative Decarbonylation of α-Quaternary Homobenzaldehydes,SynOpen

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tert-Butoxide-Mediated Protodeformylative Decarbonylation of α-Quaternary Homobenzaldehydes
SynOpen ( IF 2.0 ) Pub Date : 2024-01-19 , DOI: 10.1055/a-2231-3108
Benjamin J. Stokes ₁ , Xiao Cai ₂ , Ritter V. Amsbaugh ₁ , Lauren J. Drake ₁ , Ravi M. A. Kotamraju ₁ , Nicholas Javier C. Licauco ₁

Affiliation

tert-Butoxide mediates the Haller–Bauer-type (protodeformylative) decarbonylation of readily accessed α-quaternary homobenzaldehydes and related compounds at room temperature, generating cumene products. Both geminal dialkyl and geminal diaryl substituents are tolerated. gem-Dimethyls are sufficient for decarbonylation of polycyclic arenyl substrates whereas monocyclic aromatic homobenzaldehydes require cyclic gem-dialkyls or gem-diaryls for significant decarbonylation.

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