Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 2, Pages 534-538Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201507550
Keywords
alkenes; amination; homogeneous catalysis; iron; synthetic methods
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Funding
- NIH [GM110382]
- Georgia State University
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Reported herein is a new iron-catalyzed diastereo-selective olefin diazidation reaction which occurs at room temperature (1-5 mol% of catalysts and d.r. values of up to >20:1). This method tolerates a broad range of both unfunctionalized and highly functionalized olefins, including those that are incompatible with existing methods. It also provides a convenient approach to vicinal primary diamines as well as other synthetically valuable nitrogen-containing building blocks which are difficult to obtain with alternative methods. Preliminary mechanistic studies suggest that the reaction may proceed through a new mechanistic pathway in which both Lewis acid activation and iron-enabled redox-catalysis are crucial for selective azido-group transfer.
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