Iodine-catalyzed diazo activation to access radical reactivity

Pan Li, Jingjing Zhao, Lijun Shi, Jin Wang, Xiaodong Shi () and Fuwei Li ()
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Pan Li: Chinese Academy of Sciences
Jingjing Zhao: Chinese Academy of Sciences
Lijun Shi: Chinese Academy of Sciences
Jin Wang: University of South Florida
Xiaodong Shi: University of South Florida
Fuwei Li: Chinese Academy of Sciences

Nature Communications, 2018, vol. 9, issue 1, 1-9

Abstract: Abstract Transition-metal-catalyzed diazo activation is a classical way to generate metal carbene, which are valuable intermediates in synthetic organic chemistry. An alternative iodine-catalyzed diazo activation is disclosed herein under either photo-initiated or thermal-initiated conditions, which represents an approach to enable carbene radical reactivity. This metal-free diazo activation strategy were successfully applied into olefin cyclopropanation and epoxidation, and applying this method to pyrrole synthesis under thermal-initiated conditions further demonstrates the unique reactivity using this method over typical metal-catalyzed conditions.

Date: 2018
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DOI: 10.1038/s41467-018-04331-4

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