One-Pot Lewis Acid Mediated Water-Promoted Transformation of Styrenes to α‑Substituted Conjugated Enals

We report herein an unusual one-pot preparation of α-benzyl-substituted conjugated enals via ZnCl2/LiCl/H2O-mediated transformation of styrenes. On the basis of experimental and computational studies, an underlying mechanism including electrophilic addition and hydride transfer with iminium cations...

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Bibliographic Details
Published in:	Organic letters Vol. 25; no. 27; pp. 4996 - 5000
Main Authors:	Kudriashova, Ekaterina S., Yarushina, Margarita A., Gavryushin, Andrei E., Grishin, Ivan D., Malysheva, Yulia B., Otvagin, Vasilii F., Fedorov, Alexey Yu
Format:	Journal Article
Language:	English
Published:	United States American Chemical Society 14-07-2023
Subjects:	Lewis Acids Lithium Chloride Styrenes
Online Access:	Get full text
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Summary:	We report herein an unusual one-pot preparation of α-benzyl-substituted conjugated enals via ZnCl2/LiCl/H2O-mediated transformation of styrenes. On the basis of experimental and computational studies, an underlying mechanism including electrophilic addition and hydride transfer with iminium cations has been proposed. The effect of the LiCl/ZnCl2/H2O combination on the reaction yield has been studied, demonstrating their participation in the activation and the key isomerization of an iminium electrophile.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1523-7060 1523-7052
DOI:	10.1021/acs.orglett.3c01576