33581-42-9Relevant articles and documents
Facile and metal-free synthesis of phenols from benzaldoxime and diaryliodonium salts
Zhou, Yongsheng
, p. 591 - 593 (2017/11/14)
A metal-free, base-promoted facile synthesis of phenol derivatives utilising diaryliodonium salts as the aryl source and benzaldoxime as the hydroxide surrogate has been developed. The reaction is fast and shows good substrate compatibility, giving the corresponding products in good to excellent yields. A gram-scale synthesis of phenols utilising this protocol has also been achieved.
Synthesis of Complex Phenols Enabled by a Rationally Designed Hydroxide Surrogate
Fier, Patrick S.,Maloney, Kevin M.
, p. 4478 - 4482 (2017/04/13)
The conversion of aryl halides to phenols under mild reaction conditions is a longstanding and formidable challenge in organic chemistry. Herein, we report the rational design of a broadly applicable Pd-catalyzed method to prepare phenols with benzaldehyde oxime as a hydroxide surrogate. These reactions occur under mildly basic conditions and enable the late-stage hydroxylation of several functionally-dense drug-like aryl halides.
Cesium Carbonate Promoted Direct Arylation of Hydroxylamines and Oximes with Diaryliodonium Salts
Yang, Yang,Wu, Xunshen,Han, Jianwei,Mao, Song,Qian, Xiaofei,Wang, Limin
supporting information, p. 6854 - 6857 (2016/02/19)
A transition-metal-free approach for the arylation of hydroxylamines and oximes with diaryliodonium salts was developed. The reaction proceeded smoothly at room temperature in the presence of cesium carbonate. As a result, a wide range of N- and O-arylate
Metal-free one-pot synthesis of benzofurans
Ghosh, Raju,Stridfeldt, Elin,Olofsson, Berit
, p. 8888 - 8892 (2014/07/22)
Ethyl acetohydroxamate was efficiently arylated with diaryliodonium salts at room temperature under transition-metal-free conditions. The obtained O-arylated products were reacted in situ with ketones under acidic conditions to yield substituted benzo[b]furans through oxime formation, [3,3]-rearrangement, and cyclization in a fast and operationally simple one-pot fashion without using excess reagents. Alternatively, the O-arylated products could be isolated or transformed in situ to aryloxyamines or O-arylaldoximes. The methodology was applied to the synthesis of Stemofuran A and the formal syntheses of Coumestan, Eupomatenoid 6, and (+)-machaeriol B. Just add salt! A metal-free, room temperature arylation of ethyl acetohydroxamate, followed by an in situ reaction with ketones under acidic conditions yielded substituted benzo[b]furans in a fast and operationally simple one-pot fashion without using excess reagents (see scheme). Alternatively, the O-arylated products could be isolated, hydrolyzed in situ to aryloxyamines, or transformed to O-arylaldoximes. The efficiency of the methodology was demonstrated by the formal synthesis of several biologically active benzofurans.
Copper-mediated synthesis of substituted 2-aryl-N-benzylbenzimidazoles and 2-arylbenzoxazoles via C-H functionalization/C-N/C-O bond formation
Guru, Murali Mohan,Ali, Md Ashif,Punniyamurthy, Tharmalingam
, p. 5295 - 5308 (2011/08/05)
An efficient method for the transformation of N-benzyl bisarylhydrazones and bisaryloxime ethers to functionalized 2-aryl-N-benzylbenzimidazoles and 2-arylbenzoxazoles is described. The protocol involves a copper(II)-mediated cascade C-H functionalization/C-N/C-O bond formation under neutral conditions. Substrates having either electron-donating or -withdrawing substituents undergo the cyclization to afford the target heterocycles at moderate temperature.
Polymer-supported copper complex for the direct synthesis of O-aryloxime ethers via cross-coupling of oximes and arylboronic acids
Wang, Liang,Huang, Chengyan,Cai, Chun
experimental part, p. 532 - 536 (2010/07/16)
L-proline functionalized chloroacetylated polystyrene supported copper (II) complex was prepared and found to be effective for the cross-coupling reaction between aromatic oximes and arylboronic acids under mild conditions. Only catalytic amount of cataly
O-aryloxime ethers from the copper(II)-mediated cross-coupling of oximes and phenylboronic acids
Ali, Abdelselam,Meyer, Adam G.,Tuck, Kellie L.
scheme or table, p. 955 - 959 (2009/09/06)
A direct approach to O-aryloxime ethers by means of the first copper-mediated cross-coupling of aromatic oximes and phenylboronic acids is reported. The O-arylation of acetophenone oximes with phenylboronic acids typically furnished O-aryloxime ethers in
