One-Pot Synthesis of Polysubstituted Imidazoles Based on Pd(OAc)2/Ce(SO4)2/Bi(NO3)3 Trimetallic Cascade of Decarboxylation/Wacker-Type Oxidation/Debus-Radziszewski Reaction

被引：8

作者：

Sun, Wei ^{[1
]}

Zhang, Mingjuan ^{[1
]}

Li, Peilang ^{[1
]}

Li, Yiqun ^{[1
,2
]}

机构：

[1] Jinan Univ, Dept Chem, Guangzhou 510632, Guangdong, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2019年 / 51卷 / 17期

基金：

中国国家自然科学基金;

关键词：

Pd (II); Ce (IV); Bi (III) trimetallic system; imidazole; decarboxylation; Wacker-type oxidation; Debus-Radziszewski reaction; CROSS-COUPLING REACTIONS; C-H BONDS; 1,2,4,5-TETRASUBSTITUTED IMIDAZOLES; SUBSTITUTED IMIDAZOLES; EFFICIENT SYNTHESIS; 1,2-DIKETONES; DERIVATIVES; PALLADIUM; ARYLATION; ALKYNES;

D O I：

10.1055/s-0037-1611835

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and highly efficient one-pot synthesis of polysubstituted imidazoles from alpha-hydroxyphenylacetic acids, diphenylacetylene, and amines has been achieved by Pd(OAc) (2) /Ce(SO (4) ) (2) /Bi(NO (3) ) (3) trimetallic catalytic system. A series of control experiments showed that this overall reaction occurs through a one-pot cascade process combining the steps of decarboxylation of alpha-hydroxyphenylacetic acids, Wacker-type oxidation of diphenylacetylene, and Debus-Radziszewski annulation of aryl aldehydes and benzil generated in situ, as well as amines. This reaction represents a novel multicomponent reaction using alpha-hydroxyphenylacetic acids and diphenylacetylene as sources of aryl aldehydes and a beta-diketone. This process exhibits a broad substrate scope and a good functional group tolerance to assemble the corresponding polysubstituted imidazoles in excellent yields (72-88%) under mild conditions.

引用

页码：3221 / 3230

页数：10

共 2 条

[1] Efficient one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones from aromatic aldehydes and their one-pot oxidation to quinazolin-4(3H)-ones catalyzed by Bi(NO3)3•5H2O: Investigating the role of the catalyst
Mohammadpoor-Baltork, Iraj
Khosropour, Ahmad R.
Moghadam, Majid
Tangestaninejad, Shahram
Mirkhani, Valiollah
Baghersad, Saeid
Mirjafari, Arsalan
COMPTES RENDUS CHIMIE, 2011, 14 (10) : 944 - 952
[2] Efficient synthesis of 3-substituted 2,3-dihydroquinolin-4-ones using a one-pot sequential multi-catalytic process: Pd-catalyzed allylic amination-thiazolium salt-catalyzed Stetter reaction cascade
Nemoto, Tetsuhiro
Fukuda, Tomoaki
Hamada, Yasumasa
TETRAHEDRON LETTERS, 2006, 47 (26) : 4365 - 4368

← 1 →