Lei Bowen, Wang Xiaojiao, Ma Lifang, Jiao Huixuan, Zhu Lisi, Li Ziyuan
Department of Pharmaceutical and Biological Engineering, School of Chemical Engineering, Sichuan University, Chengdu 610065, China.
Org Biomol Chem. 2017 Jul 26;15(29):6084-6088. doi: 10.1039/c7ob01083d.
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)-C(sp) 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.
通过钯（II）催化的C-H键活化，以烷基硼酸作为烷基供体，实现了一种新颖且简洁的恶唑C5-烷基化反应，产率适中至良好，官能团耐受性令人满意。与常用的BQ作为关键促进剂不同，发现DDQ是一种更好的添加剂，能显著促进这种烷基化反应。这种高效且先进的方法代表了恶唑C5位上的首例C(sp)-C(sp)交叉偶联反应，因其在含恶唑生物活性分子后期官能化中的潜在应用而特别具有吸引力。
