DDQ-promoted direct C5-alkylation of oxazoles with alkylboronic acids via palladium-catalysed C–H bond activation. Issue 29 (7th July 2017)

• Record Type: Journal Article
• Authors: Lei, Bowen; Wang, Xiaojiao; Ma, Lifang; Jiao, Huixuan; Zhu, Lisi; Li, Ziyuan
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 29(2017)
• Page Start: 6084
• Page End: 6088
• Publication Date: 2017-07-07
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob01083d
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The first protocol for the direct C5-alkylation of oxazoles through transition-metal-catalysed C(5)–H bond activation. Abstract : A novel and concise C5-alkylation of oxazoles using alkylboronic acids as alkyl donors via Pd(ii )-catalysed C–H bond activation has been achieved in moderate to good yields with satisfactory functional group tolerance. Instead of commonly used BQ as a key promoter, DDQ was discovered to be a better additive that significantly promoted this alkylation. This efficient and advanced method represents the first C(sp 2 )–C(sp 3 ) cross-coupling reaction at the C5-position of oxazoles, which is particularly attractive due to its potential applications in the late-stage functionalization of oxazole-containing bioactive molecules.