Unexpected Phenol Production from Arylboronic Acids under Palladium-Free Conditions; Organocatalyzed Air Oxidation

作者:Cammidge Andrew N*; Goddard Victoria H M; Schubert Christopher P J; Gopee Hemant; Hughes David L; Gonzalez Lucas Daniel
来源:Organic Letters, 2011, 13(22): 6034-6037.
DOI:10.1021/ol202500z

摘要

An intriguing class of quinones that efficiently catalyze the air oxidation (overall hydroxylation) of arylboronic acids to the corresponding phenol is reported. Autocatalysis In the parent system Is particularly efficient and leads to rapid, quantitative synthesis of quinones such as 4 from boronic acid 1 at room temperature using air as stoichlometric oxidant. The efficiency results from a balance between two-stage conjugate addition and migration with each step driven by aromatization of a naphthalene fragment.

  • 出版日期2011-11-18