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Issue 57, 2021

Palladium-catalyzed cascade carbonylative annulation between alkene-tethered aryl iodides and carbon monoxide

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Abstract

Rapid construction of molecules bearing all-substituted quaternary stereocenters represents a highly significant but challenging task in organic synthesis. Herein, we report a novel palladium-catalyzed cascade between alkene-tethered aryl iodides and carbon monoxide, which has resulted in a practical and powerful method for the synthesis of complex polycyclic molecules containing aryl-substituted quaternary stereocenters. Mechanistic studies suggested that the reaction proceeded via a Heck-type carbonylative cyclization, followed by a ketene-involved Friedel–Crafts acylation.

Graphical abstract: Palladium-catalyzed cascade carbonylative annulation between alkene-tethered aryl iodides and carbon monoxide

Supplementary files

Article information


Submitted
27 Apr 2021
Accepted
14 Jun 2021
First published
15 Jun 2021

Chem. Commun., 2021,57, 7023-7026
Article type
Communication

Palladium-catalyzed cascade carbonylative annulation between alkene-tethered aryl iodides and carbon monoxide

Y. Zhang, Y. Sun, Y. Chang, H. Shao and Y. Zhao, Chem. Commun., 2021, 57, 7023 DOI: 10.1039/D1CC02217B

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