Issue 29, 2017
From the journal:

Organic & Biomolecular Chemistry

DDQ-promoted direct C5-alkylation of oxazoles with alkylboronic acids via palladium-catalysed C–H bond activation†

Bowen Lei,a   Xiaojiao Wang,a   Lifang Ma,*a   Huixuan Jiao,a   Lisi Zhua  and  Ziyuan Li ORCID logo *a  

* Corresponding authors

a Department of Pharmaceutical and Biological Engineering, School of Chemical Engineering, Sichuan University, Chengdu 610065, China
E-mail: liziyuan@scu.edu.cn, mlfang11@scu.edu.cn

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(sp2)–C(sp3) 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.

Graphical abstract: DDQ-promoted direct C5-alkylation of oxazoles with alkylboronic acids via palladium-catalysed C–H bond activation

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Article information

DOI
https://doi.org/10.1039/C7OB01083D
Article type
Communication
Submitted
04 May 2017
Accepted
01 Jul 2017
First published
03 Jul 2017

Org. Biomol. Chem., 2017,15, 6084-6088

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DDQ-promoted direct C5-alkylation of oxazoles with alkylboronic acids via palladium-catalysed C–H bond activation

B. Lei, X. Wang, L. Ma, H. Jiao, L. Zhu and Z. Li, Org. Biomol. Chem., 2017, 15, 6084 DOI: 10.1039/C7OB01083D

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