Copper(II)-catalyzed ether synthesis from aliphatic alcohols and potassium organotrifluoroborate salts

被引:200
作者
Quach, TD [1 ]
Batey, RA [1 ]
机构
[1] Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada
关键词
D O I
10.1021/ol034454n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A protocol for the copper(II)-catalyzed etherification of aliphatic alcohols under mild and essentially neutral conditions is described. Air- and moisture-stable potassium alkenyl- and aryltrifluoroborate salts undergo cross-coupling with a variety of aliphatic primary and secondary alcohols and phenols, and are tolerant of a range of functional groups. The optimized conditions utilize catalytic copper(II) acetate with 4-(dimethylamino)pyridine as ligand in the presence of 4 Angstrom molecular sieves under an atmosphere of oxygen.
引用
收藏
页码:1381 / 1384
页数:4
相关论文
共 35 条
[1]   Organoboron compounds as mild nucleophiles in Lewis acid- and transition metal-catalyzed C-C bond-forming reactions [J].
Batey, RA ;
Quach, TD ;
Shen, M ;
Thadani, AN ;
Smil, DV ;
Li, SW ;
MacKay, DB .
PURE AND APPLIED CHEMISTRY, 2002, 74 (01) :43-55
[2]   Synthesis and cross-coupling reactions of tetra alkylammonium organotrifluoroborate salts [J].
Batey, RA ;
Quach, TD .
TETRAHEDRON LETTERS, 2001, 42 (52) :9099-9103
[3]   Potassium alkenyl- and aryltrifluoroborates: Stable and efficient agents for rhodium-catalyzed addition to aldehydes and enones [J].
Batey, RA ;
Thadani, AN ;
Smil, DV .
ORGANIC LETTERS, 1999, 1 (10) :1683-1686
[4]   MACROCYCLIC ACETYLENIC COMPOUNDS .2. 1,2,7,8-DIBENZOCYCLODODECA-1,7-DIENE-3,5,9,11-TETRAYNE [J].
BEHR, OM ;
EGLINTON, G ;
GALBRAITH, AR ;
RAPHAEL, RA .
JOURNAL OF THE CHEMICAL SOCIETY, 1960, (SEP) :3614-3625
[5]   A new method for the preparation of aryl vinyl ethers [J].
Blouin, M ;
Frenette, R .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26) :9043-9045
[6]   New N- and O-arylations with phenylboronic acids and cupric acetate [J].
Chan, DMT ;
Monaco, KL ;
Wang, RP ;
Winters, MP .
TETRAHEDRON LETTERS, 1998, 39 (19) :2933-2936
[7]  
DARSES S, 1999, EUR J ORG CHEM, V1875, P5
[8]   Intramolecular O-arylation of phenols with phenylboronic acids: Application to the synthesis of macrocyclic metalloproteinase inhibitors [J].
Decicco, CP ;
Song, Y ;
Evans, DA .
ORGANIC LETTERS, 2001, 3 (07) :1029-1032
[9]  
EGLINTON G, 1956, CHEM IND-LONDON, P737
[10]   Synthesis of diaryl ethers through the copper-promoted arylation of phenols with arylboronic acids. An expedient synthesis of thyroxine [J].
Evans, DA ;
Katz, JL ;
West, TR .
TETRAHEDRON LETTERS, 1998, 39 (19) :2937-2940