Issue 78, 2020

Light-enabled, AlCl3-catalyzed regioselective intramolecular nucleophilic addition of non-nucleophilic alkyls to alkynes

Abstract

Light-enabled, AlCl3-catalyzed regioselective intramolecular nucleophilic cyclization of alkynes using non-nucleophilic alkyls as the nucleophile is reported. Upon photoexcitation, o-alkylphenyl alkynyl ketones can be transferred into (E)-photoenols. Thus, a nucleophilic methylene is formed from the non-nucleophilic alkyl. An AlCl3 catalyst can stabilize the (E)-photoenol intermediate and facilitate further intramolecular nucleophilic cyclization. DFT calculations indicated that the AlCl3-catalyzed cyclization is the regioselectivity determining step.

Graphical abstract: Light-enabled, AlCl3-catalyzed regioselective intramolecular nucleophilic addition of non-nucleophilic alkyls to alkynes

Supplementary files

Article information

Article type
Communication
Submitted
04 Jul 2020
Accepted
24 Aug 2020
First published
24 Aug 2020

Chem. Commun., 2020,56, 11621-11624

Light-enabled, AlCl3-catalyzed regioselective intramolecular nucleophilic addition of non-nucleophilic alkyls to alkynes

Y. Zhang, R. Jin, G. Pan and H. Guo, Chem. Commun., 2020, 56, 11621 DOI: 10.1039/D0CC04636A

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