Dergiler / Turkish Journal of Chemistry / 2015 / Cilt: 39 - Sayı: 1

Synthesis of tetrahydropyrimidinium salts and their in situ catalytic activities towards the Buchwald--Hartwig amination reaction under microwave irradiation

Sayfa
121–129
DOI
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Özet

A series of asymmetrical substituted tetrahydropyrimidinium salts and different kinds of bridged bis-tetrahydropyrimidinium salts were prepared through the quaterization of tetrahydropyrimidine or the dehydrogenation of hexahydropyrimidine. They were characterized and used as NHC precursors in the palladium catalyzed Buchwald--Hartwig amination reaction. The in situ formed catalytic system Pd(OAc)2/tetrahydropyrimidinium and tBuOK catalyzed the amination of heteroaryl halides and heterocyclic amines effectively, producing the heterocyclic amine functionalized heteroaryl derivatives in high yields.

Abstract

A series of asymmetrical substituted tetrahydropyrimidinium salts and different kinds of bridged bis-tetrahydropyrimidinium salts were prepared through the quaterization of tetrahydropyrimidine or the dehydrogenation of hexahydropyrimidine. They were characterized and used as NHC precursors in the palladium catalyzed Buchwald--Hartwig amination reaction. The in situ formed catalytic system Pd(OAc)2/tetrahydropyrimidinium and tBuOK catalyzed the amination of heteroaryl halides and heterocyclic amines effectively, producing the heterocyclic amine functionalized heteroaryl derivatives in high yields.

Anahtar kelimeler: Tetrahydropyrimidinium salt, Buchwald--Hartwig amination, microwave irradiation, palladium catalysis, N-heterocyclic carbene