Iron phthalocyanine-catalyzed radical phosphinoylazidation of alkenes: A facile synthesis of β-azido-phosphine oxide with a fast azido transfer step
| Autor: | Xiaoyan Li, Liang Ge, Mong-Feng Chiou, Yajun Li, Li Wu, Xiaoxu Ma, Hongli Bao |
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| Rok vydání: | 2021 |
| Předmět: |
Phosphine oxide
Chemistry Intermolecular force Iron phthalocyanine 02 engineering and technology General Medicine Activation energy 010402 general chemistry 021001 nanoscience & nanotechnology 01 natural sciences Combinatorial chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound Phthalocyanine 0210 nano-technology |
| Zdroj: | Chinese Journal of Catalysis. 42:1634-1640 |
| ISSN: | 1872-2067 |
| DOI: | 10.1016/s1872-2067(21)63847-0 |
| Popis: | Phosphinoylazidation of alkenes is a direct method to build nitrogen- and phosphorus-containing compounds from feed-stock chemicals. Notwithstanding the advances in other phosphinyl radical related difunctionalization of alkenes, catalytic phosphinoylazidation of alkenes has not yet been reported. Here, we describe the first iron-catalyzed intermolecular phosphinoylazidation of styrenes and unactivated alkenes. The method is practically useful and requires a relatively low loading of catalyst. Mechanistic studies confirmed the radical nature of the reaction and disclosed the unusually low activation energy 4.8 kcal/mol of radical azido group transfer from the azidyl iron(III) phthalocyanine species (PcFeIIIN3) to a benzylic radical. This work may help to clarify the mechanism of iron-catalyzed azidation, inspire other mechanism studies and spur further synthetic applications. |
| Databáze: | OpenAIRE |
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