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

被引:275
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
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
收藏
页码:4085 / 4089
页数:5
相关论文
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 [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
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 [J].
Basle, Olivier ;
Li, Chao-Jun .
GREEN CHEMISTRY, 2007, 9 (10) :1047-1050
[7]   Copper-catalyzed aerobic phosphonation of sp3 C-H bonds [J].
Basle, Olivier ;
Li, Chao-Jun .
CHEMICAL COMMUNICATIONS, 2009, (27) :4124-4126
[8]   Catalytic stereoselective benzylic C-H functionalizations by oxidative C-H activation and organocatalysis [J].
Benfatti, Fides ;
Capdevila, Montse Guiteras ;
Zoli, Luca ;
Benedetto, Elena ;
Cozzi, Pier Giorgio .
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 [J].
Chamberland, S ;
Woerpel, KA .
ORGANIC LETTERS, 2004, 6 (25) :4739-4741
[10]  
Chen X., 2009, ANGEW CHEM, V121, P5196