Potassium tert-Butoxide Mediated O-Arylation of N-Hydroxyphthalimide and Oximes with Diaryliodonium Salts

被引:11
作者
Castro, Luis C. Misal [1 ]
Chatani, Naoto [1 ]
机构
[1] Osaka Univ, Dept Appl Chem, Fac Engn, Suita, Osaka 5650871, Japan
来源
SYNTHESIS-STUTTGART | 2014年 / 46卷 / 17期
基金
日本科学技术振兴机构;
关键词
O-arylation; O-arylhydroxylamines; oximes; N-hydroxyphthalimide; diaryliodonium salts; TRANSITION-METAL-FREE; ONE-POT SYNTHESIS; C-H; PHENYLBORONIC ACIDS; EFFICIENT SYNTHESIS; ARYLBORONIC ACIDS; ARYLOXIME ETHERS; ARENES; PHENOXYACETAMIDES; OPTIMIZATION;
D O I
10.1055/s-0033-1340192
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A metal-free method for the direct O-arylation of N-hydroxyphthalimide, pyridine-2-carboxaldehyde oxime, acetophenone oxime, or dimethylglyoxime with diaryliodonium salts under mild reaction conditions and short reaction time in the presence of potassium tert-butoxide is reported. The diaryliodonium counterion salt plays an important role in the reaction when it is carried out at 40 degrees C or lower temperatures.
引用
收藏
页码:2312 / 2316
页数:5
相关论文
共 47 条
[1]   Metal-Free Direct Arylations of Indoles and Pyrroles with Diaryliodonium Salts [J].
Ackermann, Lutz ;
Dell'Acqua, Monica ;
Fenner, Sabine ;
Vicente, Ruben ;
Sandmann, Rene .
ORGANIC LETTERS, 2011, 13 (09) :2358-2360
[2]   Parasiticidal 2-alkoxy- and 2-aryloxyiminoalkyl trifluoromethanesulfonanilides [J].
Ali, Abdelselam ;
Altamore, Timothy M. ;
Bliese, Marianne ;
Fisara, Petr ;
Liepa, Andris J. ;
Meyer, Adam G. ;
Nguyen, Oahn ;
Sargent, Roger M. ;
Sawutz, David G. ;
Winkler, David A. ;
Winzenberg, Kevin N. ;
Ziebell, Angela .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (01) :252-255
[3]   O-Aryloxime Ethers from the Copper(II)-Mediated Cross-Coupling of Oximes and Phenylboronic Acids [J].
Ali, Abdelselam ;
Meyer, Adam G. ;
Tuck, Kellie L. .
SYNLETT, 2009, (06) :955-959
[4]  
[Anonymous], 2014, Angew. Chem, DOI DOI 10.1002/ANGE.201309650
[5]  
BALDOLI C, 1988, SYNTHESIS-STUTTGART, P344
[6]  
BAUMANN JB, 1975, SYNTHESIS-STUTTGART, P782
[7]   Regiospecific one-pot synthesis of diaryliodonium tetrafluoroborates from arylboronic acids and aryl iodides [J].
Bielawski, Marcin ;
Aili, David ;
Olofsson, Berit .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (12) :4602-4607
[8]   Efficient and general one-pot synthesis of diaryliodonium triflates: Optimization, scope and limitations [J].
Bielawski, Marcin ;
Zhu, Mingzhao ;
Olofsson, Berit .
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (17-18) :2610-2618
[9]   High-yielding one-pot synthesis of diaryliodonium triflates from arenes and iodine or aryl iodides [J].
Bielawski, Marcin ;
Olofsson, Berit .
CHEMICAL COMMUNICATIONS, 2007, (24) :2521-2523
[10]   CONVENIENT SYNTHESIS OF O-PHENYLHYDROXYLAMINE [J].
CADOGAN, JIG ;
ROWLEY, AG .
SYNTHETIC COMMUNICATIONS, 1977, 7 (06) :365-366