Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Reviews and Accounts
Generation and Cycloaddition Reactions of Transition Metal-Containing Ylides
Hiroyuki Kusama
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2012 Volume 70 Issue 4 Pages 366-381

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Abstract
The transition metal-catalyzed electrophilic activation of alkynes towards the attack of nucleophiles has been a subject of extensive study due to their high utility as useful methods for the construction of polycyclic compounds.
We have found that transition metal-containing carbonyl or azomethine ylides, novel bifunctional metal-containing reactive species, can be generated by treatment of ω-alkynyl carbonyl or imine derivatives with a catalytic amount of electrophilic transition metal complexes such as W(0) and Pt(II) complexes. These species turned out to behave both as an ylide and as a carbene complex during the reaction. Various types of heterocyclic and carbocyclic skeletons could be obtained in a single operation by using these species. Herein, we report the full account of our research based on the above methodology.
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© 2012 The Society of Synthetic Organic Chemistry, Japan
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