Issue 60, 2022

Transition-metal-free regioselective hydroamination of styrenes with amino-heteroarenes

Abstract

The base-mediated anti-Markovnikov hydroamination of functionally varied styrenes with amino-substituted pyridine, quinoline, pyrimidine, pyrazine, and phenanthridine with excellent regioselectivity has been described. Double hydroamination was observed chemoselectively on the secondary amine, leaving the primary amine intact. Experimental evidence suggests that the proposed reaction involves the nucleophilic addition of the aminopyridyl radical onto vinyl arenes via a single electron transfer.

Graphical abstract: Transition-metal-free regioselective hydroamination of styrenes with amino-heteroarenes

Supplementary files

Article information

Article type
Communication
Submitted
16 May 2022
Accepted
21 Jun 2022
First published
21 Jun 2022

Chem. Commun., 2022,58, 8424-8427

Transition-metal-free regioselective hydroamination of styrenes with amino-heteroarenes

P. Meena, Ayushee, M. Patel and A. K. Verma, Chem. Commun., 2022, 58, 8424 DOI: 10.1039/D2CC02781J

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