Journal
CHEMICAL SCIENCE
Volume 9, Issue 28, Pages 6085-6090Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8sc01882k
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Funding
- National Natural Science Foundation of China [21772113, 21302075, 11501454]
- Key Research and Development Plan of Shandong Province [2017GGX70109]
- Fundamental Research Funds of Shandong University [2017JC004]
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We describe a (salen)Mn(iii)-catalyzed three-component reaction of aldehydes, olefins, and sodium azide for the installation of two useful groups (C?O and N-3) 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.
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