Solid-phase synthesis of phenols and pyridinones via arylboronation/oxidation protocol using aryl bromides

被引:9
作者
Lee, Younghee [1 ]
Kelly, Martha J. [1 ]
机构
[1] Locus Pharmaceut Inc, Blue Bell, PA 19422 USA
关键词
solid-phase synthesis; arylboronation; oxidation; phenol; pyridinone;
D O I
10.1016/j.tetlet.2006.05.034
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A sequence of two known reactions, palladium catalyzed arylboronation of arybromide and subsequent oxidation of arylboronate with oxone, has been carried out to prepare functionalized phenols and pyridin-2(1H)-one which were later loaded on to resin for solid-phase synthesis. Using these resin-bound templates, a number of solid-phase methods were developed to generate libraries of substituted phenols and pyridin-2(1H)-one. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4897 / 4901
页数:5
相关论文
共 34 条
[1]   DIRECTED LITHIATION OF AROMATIC TERTIARY AMIDES - AN EVOLVING SYNTHETIC METHODOLOGY FOR POLYSUBSTITUTED AROMATICS [J].
BEAK, P ;
SNIECKUS, V .
ACCOUNTS OF CHEMICAL RESEARCH, 1982, 15 (10) :306-312
[2]   CARBON CARBON BOND FORMATION THROUGH ORGANOMETALLIC ELIMINATION-REACTIONS [J].
BROWN, JM ;
COOLEY, NA .
CHEMICAL REVIEWS, 1988, 88 (07) :1031-1046
[3]  
Brun EM, 2000, SYNTHESIS-STUTTGART, P273
[4]   AROMATIC-SUBSTITUTION BY SRN1 MECHANISM [J].
BUNNETT, JF .
ACCOUNTS OF CHEMICAL RESEARCH, 1978, 11 (11) :413-420
[5]   The directed ortho metalation-transition metal-catalyzed reaction symbiosis in heteroaromatic synthesis [J].
Chauder, B ;
Green, L ;
Snieckus, V .
PURE AND APPLIED CHEMISTRY, 1999, 71 (08) :1521-1529
[6]   NEW 4+1 RADICAL ANNULATIONS - A FORMAL TOTAL SYNTHESIS OF (+/-)-CAMPTOTHECIN [J].
CURRAN, DP ;
LIU, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) :5863-5864
[7]   Palladium-catalyzed enyne-yne [4+2] benzannulation as a new and general approach to polysubstituted benzenes [J].
Gevorgyan, V ;
Yamamoto, Y .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :232-247
[8]   Formation of aryl-nitrogen, aryl-oxygen, and aryl-carbon bonds using well-defined copper(I)-based catalysts [J].
Gujadhur, RK ;
Bates, CG ;
Venkataraman, D .
ORGANIC LETTERS, 2001, 3 (26) :4315-4317
[9]   Preparation and photochemical rearrangements of 2-phenyl-2,5-cyclohexadien-1-ones. An efficient route to highly substituted phenols [J].
Guo, ZH ;
Schultz, AG .
ORGANIC LETTERS, 2001, 3 (08) :1177-1180
[10]   NON-CONVENTIONAL ELECTROPHILIC AROMATIC SUBSTITUTIONS AND RELATED REACTIONS [J].
HARTSHORN, SR .
CHEMICAL SOCIETY REVIEWS, 1974, 3 (02) :167-192