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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 50, 2020 - Issue 24
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Articles

Mizoroki–Heck reaction of 1,2-disubstituted aryl alkenes: Variables of synthesis, solvent and ligand modulation of reactivity

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Pages 3796-3803 | Received 22 May 2020, Published online: 27 Aug 2020
 

Abstract

Reaction of aryl iodides with 1,2-disubstituted aryl alkenes in the presence of TBABr/TBACl gave high yields of the Mizoroki–Heck product. Phosphine ligands were used for the modulation of reactivity and stereoselectivity, for the reaction of 4-iodoanisole with cinnamaldehyde. tert-Bu3P.HBF4 gave the highest E:Z ratio of 1:0.08. The use of PEG-200 and PEG-400 as solvent could activate the reaction of aryl iodides with various 1,2-disubstituetd aryl alkenes.

Graphical Abstract

Acknowledgments

Financial support is gratefully acknowledged from the CSIR Network Project, ORIGIN – under the XII Five year plan CSC 0108 and PGB thanks the UGC for a SRF.

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