Cobalt-Catalyzed Multi-Substituted Alkene Synthesis from 1,3-Dithiolanes and Grignard Reagents

The cobalt-catalyzed reaction between 1,3-dithiolanes and Grignard reagents, for the efficient synthesis of multi-substituted alkene products, is described. The method was applicable to a variety of benzylic dithiolane substrates, affording di-, tri-, and tetra-substituted 1,1-diaryl alkene products...

Full description

Saved in:
Bibliographic Details
Published inAsian journal of organic chemistry Vol. 12; no. 9
Main Authors Davidson, Timothy A. A., Anam, Samiha, Shi, Heyao, Dixon, Darren J. J.
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.09.2023
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
C-S activation
Alkene synthesis
ACTIVATION
BENZYLIC DITHIOACETALS
BOND FORMATION
Cobalt
BROMIDES
ALKYL-HALIDES
1
Grignard reagent
3-Dithiolane
OLEFINATION
COUPLING REACTION
ARYL
THIOACETALIZATION
EFFICIENT
Online AccessGet more information

Cover

More Information
Summary:The cobalt-catalyzed reaction between 1,3-dithiolanes and Grignard reagents, for the efficient synthesis of multi-substituted alkene products, is described. The method was applicable to a variety of benzylic dithiolane substrates, affording di-, tri-, and tetra-substituted 1,1-diaryl alkene products in good to excellent yields. The use of benzylic Grignard reagents with aryl aldehyde-derived 1,3-dithiolanes enabled access to natural product-derived stilbene architectures with exquisite E selectivity. The operational simplicity, low catalyst loadings, and scalability demonstrate the general utility of the method.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202300269