An Unexpected Role of a Trace Amount of Water in Catalyzing Proton Transfer in Phosphine-Catalyzed (3 + 2) Cycloaddition of Allenoates and Alkenes

Through the joint forces of computation and experiment, the detailed mechanism of the Lu phosphine catalyzed (3 + 2) cycloaddition of allenoates and alkenes has been elucidated. The overall potential energy surface of the Lu (3 + 2) reaction has been computed. More importantly, theory and experiment...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2007-03, Vol.129 (12), p.3470-3471
Main Authors: Xia, Yuanzhi, Liang, Yong, Chen, Yuanyuan, Wang, Ming, Jiao, Lei, Huang, Feng, Liu, Song, Li, Yahong, Yu, Zhi-Xiang
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Catalysis
Molecular Structure
Naphthalenes - chemistry
Phosphines - chemistry
Protons
Water - chemistry
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Summary:Through the joint forces of computation and experiment, the detailed mechanism of the Lu phosphine catalyzed (3 + 2) cycloaddition of allenoates and alkenes has been elucidated. The overall potential energy surface of the Lu (3 + 2) reaction has been computed. More importantly, theory and experiment have confirmed that a trace amount of water plays a critical role in assisting the process of [1,2] proton shift in the Lu reaction.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja068215h