Transition-metal-free, one-pot synthesis of benzoxaboroles from o-bromobenzaldehydes via visible-light-promoted borylation. Issue 47 (24th November 2021)

• Record Type: Journal Article
• Authors: Luo, Jinghan; Jia, Xingxing; Hu, Yanjun; Chen, Jianchao; Sun, Tiemin
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 47(2021)
• Page Start: 10455
• Page End: 10459
• Publication Date: 2021-11-24
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob01853a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A novel and practical approach for the synthesis of benzoxaboroles from o -bromobenzaldehydes is described via visible-light-promoted borylation. Abstract : A novel and simple one-pot stepwise method to synthesize benzoxaboroles was demonstrated. This step-by-step synthetic method includes photocatalytic boronization with phenothiazine as a photocatalyst and sequential water-induced reduction in the presence of bis(pinacolato)diboron. A series of o -bromobenzaldehydes were well-tolerated under the standard conditions. In addition, this method has been successfully applied in the synthesis of the anti-tuberculosis candidate drug GSK 3036656 and anti-fungal drug tavaborole.