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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Bibliographic Details
Published in:Angewandte Chemie International Edition Vol. 55; no. 2; pp. 534 - 538
Main Authors: Yuan, Yong-An, Lu, Deng-Fu, Chen, Yun-Rong, Xu, Hao
Format: Journal Article
Language:English
Published: Weinheim WILEY-VCH Verlag 11.01.2016
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
Edition:International ed. in English
Subjects:
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
Online Access:Get full text
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Summary: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.
Bibliography: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
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201507550