Issue 4, 2022

Planar Blatter radicals through Bu3SnH- and TMS3SiH-assisted cyclization of aryl iodides: azaphilic radical addition

Abstract

Bu3SnH- and TMS3SiH-assisted cyclizations of iodoarene derivatives of benzo[e][1,2,4]triazine lead to the formation of planar Blatter radicals (2-phenyl-3H-[1,2,4]triazino[5,6,1-kl]phenoxazin-3-yls and 2-phenyl-3H-[1,2,4]triazino[5,6,1-kl]phenothiazin-3-yls) in yields of up to 96%. The cyclization step involves the thermodynamically favored (DFT: ΔG298 = 3.1 kcal mol−1 and ΔH = –55.3 kcal mol−1) unprecedented attack of a C-centered radical on the heterocyclic N atom. This method opens up access to functionalized sulfur-containing planar Blatter radicals for the first time. New radicals were characterized using spectroscopic (UV–vis, EPR), electrochemical, and single-crystal X-ray diffraction methods.

Graphical abstract: Planar Blatter radicals through Bu3SnH- and TMS3SiH-assisted cyclization of aryl iodides: azaphilic radical addition

Supplementary files

Article information

Article type
Research Article
Submitted
22 Nov. 2021
Accepted
09 Dec. 2021
First published
10 Dec. 2021

Org. Chem. Front., 2022,9, 929-938

Planar Blatter radicals through Bu3SnH- and TMS3SiH-assisted cyclization of aryl iodides: azaphilic radical addition

P. Bartos, M. Celeda, A. Pietrzak and P. Kaszyński, Org. Chem. Front., 2022, 9, 929 DOI: 10.1039/D1QO01742J

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