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Is the reaction sequence in phosphine-catalyzed [8+2] cycloaddition controlled by electrophilicity?

Authors :
Lin WX
Pei Z
Gong C
Mo H
Yang K
Qu LB
Wei D
Song JS
Li SJ
Lan Y
Source :
Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2021 Jan 26; Vol. 57 (6), pp. 761-764.
Publication Year :
2021

Abstract

In the presence of multiple electrophiles, the reaction sequence is a critical mechanistic problem. Here, we report a theoretical study on the mechanism of phosphine-catalyzed [8+2] cycloaddition of heptafulvenes and allenoate. DFT calculations showed that electrophilicity is the barrier for nucleophilic attack, while it fails in the prediction of priority.

Details

Language :
English
ISSN :
1364-548X
Volume :
57
Issue :
6
Database :
MEDLINE
Journal :
Chemical communications (Cambridge, England)
Publication Type :
Academic Journal
Accession number :
33350413
Full Text :
https://doi.org/10.1039/d0cc07370a