Synlett 2013; 24(4): 499-501
DOI: 10.1055/s-0032-1318197
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© Georg Thieme Verlag Stuttgart · New York

A Mild and Highly Efficient Conversion of Arylboronic Acids into Phenols by Oxidation with MCPBA

Dong-Song Chen
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong 510640, P. R. of China   Fax: +86(20)87110622   eMail: chehjm@scut.edu.cn
,
Jing-Mei Huang*
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, Guangdong 510640, P. R. of China   Fax: +86(20)87110622   eMail: chehjm@scut.edu.cn
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Publikationsverlauf

Received: 05. Dezember 2012

Accepted after revision: 17. Januar 2013

Publikationsdatum:
06. Februar 2013 (online)


Abstract

A mild and highly efficient synthesis of phenols from arylboronic acids in a H2O–EtOH (1:2) solution was achieved by using MCPBA as the oxidant at room temperature. Isotopical labeling studies had shown that the hydroxyl oxygen atom of the phenol might originate from the MCPBA.

Supporting Information

 
  • References and Notes

  • 5 Tap water was applied. The same results were obtained from ultrapure water.
  • 7 General Procedure for the Hydroxylation of Phenylboronic Acid To the mixture of phenylboronic acid (0.5 mmol) in a H2O–EtOH (1:2) solution (2 mL) in a round-bottom flask was added MCPBA (0.5 mmol) at r.t. When phenylboronic acid was completely consumed (monitored by TLC, 6 h), 0.1 M aq NaHCO3 (5 mL) was added to the mixture. Then the reaction mixture was extracted with EtOAc (2 × 15 mL). The combined organic layer was washed with H2O (10 mL) and brine (5 mL), dried over anhyd MgSO4, filtered, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel (PE–EtOAc = 4:1), and the corresponding phenol was obtained as a colorless solid (2a, 46 mg, 97%).