Bu4NI-Catalyzed C-O Bond Formation by Using a Cross-Dehydrogenative Coupling (CDC) Reaction

被引：273

作者：

Chen, Long ^{[1
]}

Shi, Erbo ^{[1
]}

Liu, Zhaojun ^{[1
]}

Chen, Shulin ^{[1
]}

Wei, Wei ^{[1
]}

Li, Hong ^{[1
]}

Xu, Kai ^{[1
]}

Wan, Xiaobing ^{[1
,2
]}

机构：

[1] Soochow Suzhou Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China

[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2011年 / 17卷 / 15期

基金：

中国国家自然科学基金;

关键词：

carboxylic acids; cross-coupling; ethers; oxidation; reaction mechanisms; H BOND; OXIDATIVE ALKYLATION; CATALYZED AMIDATION; PRINS CYCLIZATIONS; DIRECT ARYLATION; ALPHA-ARYLATION; BENZYL ETHERS; ACTIVATION; FUNCTIONALIZATION; ACID;

D O I：

10.1002/chem.201100192

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The crème de la crème! A practical and simple Bu 4NI-catalyzed C-O bond formation was achieved by using a cross-dehydrogenative coupling (CDC) reaction with tert-butyl hydroperoxide (TBHP) as the ultimate oxidant (see scheme; R1=aryl, heteroaryl, alkyl; R2, R3=alkyl, alkyl halide). This approach is the most straightforward method to date for the synthesis of α-acyloxy ethers. A plausible mechanism has been proposed. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：4085 / 4089

页数：5

共 96 条

[1] Ackermann L., 2009, ANGEW CHEM, V121, P9976, DOI DOI 10.1002/ANGE.200902996
[2] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage
Ackermann, Lutz
Vicente, Ruben
Kapdi, Anant R.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) : 9792 - 9826
[3] [Anonymous], ANGEW CHEM
[4] [Anonymous], 2009, ANGEW CHEM
[5] [Anonymous], 2009, ANGEW CHEM
[6] Copper catalyzed oxidative alkylation of sp3 C-H bond adjacent to a nitrogen atom using molecular oxygen in water
Basle, Olivier
Li, Chao-Jun
[J]. GREEN CHEMISTRY, 2007, 9 (10) : 1047 - 1050
[7] Copper-catalyzed aerobic phosphonation of sp3 C-H bonds
Basle, Olivier
Li, Chao-Jun
[J]. CHEMICAL COMMUNICATIONS, 2009, (27) : 4124 - 4126
[8] Catalytic stereoselective benzylic C-H functionalizations by oxidative C-H activation and organocatalysis
Benfatti, Fides
Capdevila, Montse Guiteras
Zoli, Luca
Benedetto, Elena
Cozzi, Pier Giorgio
[J]. CHEMICAL COMMUNICATIONS, 2009, (39) : 5919 - 5921
[9] Using nucleophilic substitution reactions to understand how a remote alkyl or alkoxy substituent influences the conformation of eight-membered ring oxocarbenium ions
Chamberland, S
Woerpel, KA
[J]. ORGANIC LETTERS, 2004, 6 (25) : 4739 - 4741
[10] Chen X., 2009, ANGEW CHEM, V121, P5196

← 1 2 3 4 5 6 7 8 9 10 →