Iron-catalyzed carboazidation of alkenes and alkynes

Haigen Xiong, Nagarajan Ramkumar, Mong-Feng Chiou, Wujun Jian, Yajun Li, Ji-Hu Su, Xinhao Zhang and Hongli Bao ()
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Haigen Xiong: Chinese Academy of Sciences
Nagarajan Ramkumar: Chinese Academy of Sciences
Mong-Feng Chiou: Chinese Academy of Sciences
Wujun Jian: Chinese Academy of Sciences
Yajun Li: Chinese Academy of Sciences
Ji-Hu Su: University of Science and Technology of China
Xinhao Zhang: Peking University Shenzhen Graduate School
Hongli Bao: Chinese Academy of Sciences

Nature Communications, 2019, vol. 10, issue 1, 1-7

Abstract: Abstract Carboazidation of alkenes and alkynes holds the promise to construct valuable molecules directly from chemical feedstock therefore is significantly important. Although a few examples have been developed, there are still some unsolved problems and lack of universal methods for carboazidation of both alkenes and alkynes. Here we describe an iron-catalyzed rapid carboazidation of alkenes and alkynes, enabled by the oxidative radical relay precursor t-butyl perbenzoate. This strategy enjoys success with a broad scope of alkenes under mild conditions, and it can also work with aryl alkynes which are challenging substrates for carboazidation. A large number of diverse structures, including many kinds of amino acid precursors, fluoroalkylated vinyl azides, other specific organoazides, and 2H-azirines can be easily produced.

Date: 2019
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DOI: 10.1038/s41467-018-07985-2

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