Initiation and Termination Mode of Enyne Cross-Metathesis and Metallotropic [1,3]-Shift Controlled by Remote Substituents

The cross-metathesis of terminal alkyne and alkene using Ru-based Grubbs catalyst generally undergoes α-insertion. In this study, excellent control over α- and β-insertion of ruthenium alkylidene into terminal alkynes has been achieved by using a substituent at a remote site from the reaction center...

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Veröffentlicht in:	Journal of the American Chemical Society 2010-07, Vol.132 (26), p.8840-8841
Hauptverfasser:	Yun, Sang Young, Wang, Kung-Pern, Kim, Mansuk, Lee, Daesung
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Sprache:	eng
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creator	Yun, Sang Young Wang, Kung-Pern Kim, Mansuk Lee, Daesung
description	The cross-metathesis of terminal alkyne and alkene using Ru-based Grubbs catalyst generally undergoes α-insertion. In this study, excellent control over α- and β-insertion of ruthenium alkylidene into terminal alkynes has been achieved by using a substituent at a remote site from the reaction center. While the origin of this regioselectivity of insertion and metallotropic shift remains to be established, the trend indicates that the α-insertion with a concomitant metallotropic shift is favored with small substituents whereas the β-insertion without a metallotropic shift is favored with bulky substituents such as tert-butyl and trialkyl silyl groups.
doi_str_mv	10.1021/ja1020525
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title	Initiation and Termination Mode of Enyne Cross-Metathesis and Metallotropic [1,3]-Shift Controlled by Remote Substituents
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