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

Authors

LIANGRU YANG
HUANYU BIAN
WENPENG MAI
PU MAO
YONGMEI XIAO
DONG WEI
LINGBO QU

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.

DOI

10.3906/kim-1404-67

Keywords

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

First Page

121

Last Page

129

Recommended Citation

YANG, LIANGRU; BIAN, HUANYU; MAI, WENPENG; MAO, PU; XIAO, YONGMEI; WEI, DONG; and QU, LINGBO (2015) "Synthesis of tetrahydropyrimidinium salts and their in situ catalytic activities towards the Buchwald--Hartwig amination reaction under microwave irradiation," Turkish Journal of Chemistry: Vol. 39: No. 1, Article 11. https://doi.org/10.3906/kim-1404-67
Available at: https://journals.tubitak.gov.tr/chem/vol39/iss1/11