Issue 17, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Acid- or base-promoted photostimulated homolytic tert-butylation of pyridines and thiophenes

Byeong Hyo Kim,*a   Insik Jeon,a   Tae Hee Han,a   Hae Jin Parka  and  Young Moo Juna  

* Corresponding authors

a Department of Chemistry, Kwangwoon University, Seoul, Korea

Abstract

Regioselective photostimulated homolytic tert-butylations for heteroaromatics such as pyridines or thiophenes are investigated with tert-butylmercury(II) chloride in the presence of toluene-p-sulfonic acid (PTSA) or 1,4-diazabicyclo[2.2.2]octane (DABCO) respectively. While the promotion effect of acid is quite strong for basic pyridines, the acid does not promote the reaction effectively for non-basic thiophenes. On the other hand, pyridines and thiophenes exhibit similar tendency for the base-promoted homolytic tert-butylations, and the reactivity is mainly controlled by substituent carbonyl or cyano groups as well as by regioselectivity.

Graphical abstract: Acid- or base-promoted photostimulated homolytic tert-butylation of pyridines and thiophenes

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Article information

DOI
https://doi.org/10.1039/B104906M
Article type
Paper
Submitted
05 Jun 2001
Accepted
04 Jul 2001
First published
16 Aug 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 2035-2039

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Acid- or base-promoted photostimulated homolytic tert-butylation of pyridines and thiophenes

B. H. Kim, I. Jeon, T. H. Han, H. J. Park and Y. M. Jun, J. Chem. Soc., Perkin Trans. 1, 2001, 2035 DOI: 10.1039/B104906M

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