Iron-catalyzed carboazidation of alkenes and alkynes

• Published in: Nature communications Vol. 10; no. 1; pp. 122 - 7
• Main Authors: Xiong, Haigen, Ramkumar, Nagarajan, Chiou, Mong-Feng, Jian, Wujun, Li, Yajun, Su, Ji-Hu, Zhang, Xinhao, Bao, Hongli
• Format: Journal Article
• Language: English
• Published: London Nature Publishing Group UK 10.01.2019; Nature Publishing Group; Nature Portfolio
• Subjects: 140/131; 140/58; 639/638/403/933; 639/638/77/888; Alkenes; Alkynes; Amino acids; Aromatic compounds; Humanities and Social Sciences; Iron; Laboratories; multidisciplinary; Organic chemistry; Precursors; Reagents; Science; Science (multidisciplinary); Substrates
• ISSN: 2041-1723; 2041-1723
• DOI: 10.1038/s41467-018-07985-2

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 2 H -azirines can be easily produced. Carboazidation of alkenes and alkynes holds the promise to construct valuable, functionalized molecules. Here, the authors report a general and efficient iron-catalyzed carboazidation of both alkenes and alkynes enabled by t -butyl perbenzoate.