Work

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

Year: 2023

Type: article

Abstract: 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.

Source: SynOpen

DOI: 10.1055/a-2231-3108

Authors: Benjamin J. Stokes, Xiao Cai, Ritter V. Amsbaugh, Lauren J. Drake, Ravi M. A. Kotamraju, Nicholas Javier C. Licauco

Institutions: Santa Clara University, University of California System

Language: English

Topic: Chemical Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $340

Funders: Santa Clara University, University of California Merced