Efficient and Reliable Iodination and O-Methylation of Fluorinated Phenols

被引:13
作者
Francke, Robert [1 ]
Schnakenburg, Gregor [2 ]
Waldvogel, Siegfried R. [1 ]
机构
[1] Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany
[2] Univ Bonn, Xray Anal Dept, Inst Inorgan Chem, D-53121 Bonn, Germany
关键词
Iodination; Phenols; Oxidation; Alkylation; Fluorinated compounds; DEHYDRODIMERIZATION;
D O I
10.1002/ejoc.201000161
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Fluorinated phenols and other electron-deficient phenolic substrates are efficiently and cleanly iodinated by an iodine/iodide mixture employing alkaline conditions. This protocol turned out to be the most practical for the generation of such highly fluorinated iodophenols. For later application in coupling processes the protection of the phenolic hydroxy moiety is often required. Therefore, a practical iodination and subsequent methylation sequence was elaborated providing the highly fluorinated anisoles with good to excellent yields. The developed method is applicable for a broad scope of fluorinated phenols and analogues.
引用
收藏
页码:2357 / 2362
页数:6
相关论文
共 42 条
[1]  
Ackermann L, 2009, MODERN ARYLATION METHODS, P1
[2]   Syntheses and X-ray crystal structures of derivatives of 2,2′,4,4′,6,6′-hexaiodobiphenyl [J].
Anelli, PL ;
Brocchetta, M ;
Maffezzoni, C ;
Paoli, P ;
Rossi, P ;
Uggeri, F ;
Visigalli, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (10) :1175-1181
[3]   Selective solid-phase iodination of phenolic groups with bis(pyridine)iodonium (I) tetrafluoroborate [J].
Arsequell, G ;
Espuña, G ;
Valencia, G ;
Barluenga, J ;
Carlón, RP ;
González, JM .
TETRAHEDRON LETTERS, 1999, 40 (40) :7279-7282
[4]   N-Halogeno compounds.: Part 20.: Vicarious electrophilic fluorodemethylation of 1,3,5-trimethoxybenzene and 2,4,6-trimethoxytoluene with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor™ reagent F-TEDA-BF4) [J].
Banks, RE ;
Besheesh, MK ;
Górski, RW ;
Lawrence, NJ ;
Taylor, AJ .
JOURNAL OF FLUORINE CHEMISTRY, 1999, 96 (02) :129-133
[5]   Iodination of aromatic residues in peptides by reaction with IPy(2)BF(4) [J].
Barluenga, J ;
GarciaMartin, MA ;
Gonzalez, JM ;
Clapes, P ;
Valencia, G .
CHEMICAL COMMUNICATIONS, 1996, (13) :1505-1506
[6]   A SIMPLE AND GENERAL-ROUTE TO ARYL IODIDES FROM ARENES [J].
BARLUENGA, J ;
CAMPOS, PJ ;
GONZALEZ, JM ;
ASENSIO, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (11) :2623-2624
[7]   Synthesis of dibromotetraalkoxybiphenyls using ferric chloride [J].
Boden, N ;
Bushby, RJ ;
Lu, ZB ;
Headdock, G .
TETRAHEDRON LETTERS, 2000, 41 (51) :10117-10120
[8]   The preparation and properties of polyfluoro aromatic and heteroaromatic compounds [J].
Brooke, GM .
JOURNAL OF FLUORINE CHEMISTRY, 1997, 86 (01) :1-76
[9]   The chlorination of iodophenols - Part III The chlorination of o-iodophenol [J].
Buchan, S ;
McCombie, H .
JOURNAL OF THE CHEMICAL SOCIETY, 1931, :137-144
[10]  
Cepanec I., 2004, Synthesis of Biaryls