Zhang Liang, Liu Shuya, Zhao Zhiguo, Su Hongmei, Hao Jingcheng, Wang Yao
School of Chemistry and Chemical Engineering , Key Laboratory of the Colloid and Interface Chemistry , Shandong University , 27 Shanda Nanlu , Jinan 250100 , Shandong , China . Email:
Chem Sci. 2018 Jun 19;9(28):6085-6090. doi: 10.1039/c8sc01882k. eCollection 2018 Jul 28.
We describe a (salen)Mn(iii)-catalyzed three-component reaction of aldehydes, olefins, and sodium azide for the installation of two useful groups (C[double bond, length as m-dash]O and N) into the double bond. Traditionally, (salen)Mn(iii) in conjunction with iodosobenzene is a classical catalysis system for epoxidation of olefins. Owing to the highly competitive oxygenation approaches, it is a true challenge to establish a distinct strategy for the exploration of new olefin transformations based on this (salen)Mn(iii) catalysis system. Herein, the key to this (salen)Mn(iii)-catalyzed acylazidation of olefins was the rational application of the distinct reactivity of oxomanganese(v) species which is capable of abstracting a hydrogen atom from a substrate C-H bond. This chemoselective reaction occurred in a precisely designed reaction sequence and tolerates complex molecular structures.
我们描述了一种（salen）Mn（iii）催化的醛、烯烃和叠氮化钠的三组分反应，用于将两个有用的基团（C=O和N）引入双键。传统上，（salen）Mn（iii）与亚碘酰苯结合是烯烃环氧化的经典催化体系。由于存在高度竞争的氧化方法，基于这种（salen）Mn（iii）催化体系建立一种独特的策略来探索新的烯烃转化是一项真正的挑战。在此，这种（salen）Mn（iii）催化的烯烃酰基叠氮化反应的关键在于合理应用能够从底物C-H键中提取氢原子的氧锰（v）物种的独特反应性。这种化学选择性反应以精确设计的反应顺序发生，并且能够耐受复杂的分子结构。
