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

Wen-Xuan Lin; Zhuolin Pei; Cunxi Gong; Huilin Mo; Kai Yang; Ling-Bo Qu; Donghui Wei; Jin-Shuai Song; Shi-Jun Li; Yu Lan

doi:10.1039/D0CC07370A

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

Wen-Xuan Lin,^a Zhuolin Pei,^a Cunxi Gong,^a Huilin Mo,^a Kai Yang,^a Ling-Bo Qu,^a Donghui Wei,

^a Jin-Shuai Song,

*^a Shi-Jun Li

*^a and Yu Lan

*^ab

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* Corresponding authors

^a Green Catalysis Center, and College of Chemistry, Zhengzhou University, 100 Science Avenue, Zhengzhou, Henan, P. R. China
E-mail: jssong@zzu.edu.cn, lishijunzong@zzu.edu.cn

^b School of Chemistry and Chemical Engineering, and Chongqing Key Laboratory of Theoretical and Computational Chemistry, Chongqing University, Chongqing 400030, P. R. China
E-mail: lanyu@cqu.edu.cn

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.

Chemical Communications

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

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

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