The highly efficient air oxidation of aryl and alkyl boronic acids by a microwave-assisted protocol under transition metal-free conditions

• Published in: Green chemistry : an international journal and green chemistry resource : GC Vol. 21; no. 17; pp. 4614 - 4618
• Main Authors: Yin, Weiyan, Pan, Xizhi, Leng, Wenxi, Chen, Jian, He, Haifeng
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 2019; Royal Society of Chemistry
• Subjects: Acids; Alcohol; Alcohols; Aromatic compounds; Chemical synthesis; Chemistry; Chemistry, Multidisciplinary; Functional groups; Green & Sustainable Science & Technology; Green chemistry; Hydroxylation; Metals; Organic chemistry; Oxidation; Oxygen; Phenols; Physical Sciences; Science & Technology; Science & Technology - Other Topics; Sustainable development; Transition metals; MILD; ROOM-TEMPERATURE; CATALYSIS; PHENOLS; CONVERSION; O-2; ESTERS; IPSO-HYDROXYLATION; LIGAND; ARYLBORONIC ACIDS
• ISSN: 1463-9262; 1463-9270
• DOI: 10.1039/c9gc01965k

Molecular oxygen is the most important green-oxidant due to its excellent properties. However, the effective utilization of molecular oxygen remains a major challenge in modern chemistry. Herein, we report the development a rapid, green and efficient microwave-assisted protocol for the air oxidation of boronic acids to phenols and alcohols under transition metal-free conditions. In the presence of KOH and DMSO, high yields of the expected phenols and alcohol were obtained with microwave-assistance, and a variety of functional groups were tolerated in this procedure. Notably, this transition metal-free method represents a breakthrough in both organic synthesis and green chemistry for the oxidative hydroxylation of boronic acids to phenols and alcohols. A rapid, green and efficient microwave-assisted protocol is developed for the air oxidation of boronic acids to phenols and alcohols under transition metal-free conditions.