Issue 16, 2023

Oxidative Mizoroki–Heck reaction of unprotected cinnamylamines at ambient temperature under air

Abstract

Cinnamylamines make-up many important drugs that target G protein-coupled receptors. While 3,3-diarylallylamines can be prepared via existing synthetic methods, these often require poorly-selective Wittig addition to unsymmetrical ketones, and multistep sequences thereafter to reach the allylamine product. Methods that make use of direct aryl addition to N-protected cinnamylamines via a Mizoroki–Heck pathway are known, however, unprotected cinnamylamines are sensitive to a mixture of C–H activation and Mizoroki–Heck arylation under Pd-catalysed arylation conditions using aryl iodides. This leads to a decrease in the trans/cis selectivity that can be achieved under these reaction conditions. By reimagining the reaction and using aryl boronic acids, we have herein demonstrated how in many cases the yield and E/Z selectivity can be improved. The in situ-formed active catalyst is more sensitive under these conditions, and was observed to shut down at elevated temperatures.

Graphical abstract: Oxidative Mizoroki–Heck reaction of unprotected cinnamylamines at ambient temperature under air

Supplementary files

Article information

Article type
Research Article
Submitted
25 mai 2023
Accepted
28 jun 2023
First published
04 jul 2023

Org. Chem. Front., 2023,10, 3982-3988

Author version available

Oxidative Mizoroki–Heck reaction of unprotected cinnamylamines at ambient temperature under air

O. N. Farinde, V. Satheesh, K. K. Shrestha, C. R. Rhinehalt, V. G. Landge and M. C. Young, Org. Chem. Front., 2023, 10, 3982 DOI: 10.1039/D3QO00778B

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