Iron-Catalyzed Direct Diazidation for a Broad Range of Olefins

Reported herein is a new iron‐catalyzed diastereoselective 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...

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Vydáno v:	Angewandte Chemie International Edition Ročník 55; číslo 2; s. 534 - 538
Hlavní autoři:	Yuan, Yong-An, Lu, Deng-Fu, Chen, Yun-Rong, Xu, Hao
Médium:	Journal Article
Jazyk:	angličtina
Vydáno:	Weinheim WILEY-VCH Verlag 11.01.2016 WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc
Vydání:	International ed. in English
Témata:	Alkenes Alkenes - chemistry amination Azides - chemistry Catalysis Catalysts Chemistry Chemistry, Multidisciplinary Diamines homogeneous catalysis Iron Iron - chemistry Lewis acid Physical Sciences Science & Technology synthetic methods Temperature effects ALKENE DIAMINATION CONVENIENT ACCESS INTRAMOLECULAR AMINOHYDROXYLATION CONJUGATED DIENES alkenes BOND-CLEAVAGE homogeneous catalysis HYPERVALENT IODINE AZIDATION CHEMISTRY iron FUNCTIONALIZED HYDROXYLAMINES amination synthetic methods ALKYL AZIDES
ISSN:	1433-7851, 1521-3773
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Shrnutí:	Reported herein is a new iron‐catalyzed diastereoselective 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. With iron hand: The title reaction proceeds at room temperature and tolerates a broad range of both unfunctionalized and highly functionalized olefins. It also provides a convenient synthetic approach to a variety of nitrogen‐containing building blocks. Preliminary mechanistic studies suggest both Lewis acid activation and iron‐enabled redox catalysis are crucial for the selective azido‐group transfer.
Bibliografie:	ark:/67375/WNG-5X6PLSZ3-2 ArticleID:ANIE201507550 NIH - No. GM110382 istex:296FDE023F86C64EF51DDE65C28E417C5492CFA1 These authors contributed equally to this work. NIH RePORTER ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201507550