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research article

Intramolecular palladium-catalyzed alkene carboalkynylation

Nicolai, Stefano  
•
Swallow, Peter
•
Waser, Jerome  
2015
Tetrahedron

Carbocycles are essential building blocks for the synthesis of natural and synthetic bioactive compounds. Herein, we report the first example of palladium-catalyzed intramolecular carboalkynylation of non-activated olefins. Using activated carbonyl compounds as nucleophiles and an alkynyl bromide as an electrophile, the reaction gives access to cyclopentanes in 44-93% yield and one example of cyclohexane in 31% yield with simultaneous formation of a SP3-SP C-C bond. The reaction therefore combines ring formation with the introduction of a versatile triple bond for further functionalization. (C) 2015 Elsevier Ltd. All rights reserved.

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Type
research article
DOI
10.1016/j.tet.2015.06.030
Web of Science ID

WOS:000358973200030

Author(s)
Nicolai, Stefano  
Swallow, Peter
Waser, Jerome  
Date Issued

2015

Publisher

Elsevier

Published in
Tetrahedron
Volume

71

Issue

35

Start page

5959

End page

5964

Subjects

Catalysis

•

Alkynes

•

Alkenes

•

Multi-functionalization

•

Carbocycles

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LCSO  
Available on Infoscience
September 28, 2015
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/118700
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