Tunable carbon-carbon and carbon-sulfur cross-coupling of boronic acids with 3,4-dihydropyrimidine-2-thiones

被引：149

作者：

Lengar, A ^{[1
]}

Kappe, CO ^{[1
]}

机构：

[1] Karl Franzens Univ Graz, Inst Chem, A-8010 Graz, Austria

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 05期

关键词：

D O I：

10.1021/ol036496h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Direct microwave-assisted Pd(0)-catalyzed/Cu(1)-mediated carbon-carbon cross-coupling of 3,4-dihydropyrimidine-2-thiones and boronic acids under Liebeskind-Srogl conditions leads to 2-aryl-1,4-dihydropyrimidines in moderate to high yield. In contrast, Cu(II)-mediated reaction of the same substrates leads to carbon-sulfur cross-coupling.

引用

页码：771 / 774

页数：4

共 32 条

[1] Copper(I)-promoted palladium-catalyzed cross-coupling of unsaturated tri-n-butylstannane with heteroaromatic thioether [J].

Alphonse, FA ;

Suzenet, F ;

Keromnes, A ;

Lebret, B ;

Guillaumet, G .

ORGANIC LETTERS, 2003, 5 (06) :803-805

[2]

Alphonse FA, 2002, SYNLETT, P447

[3] DIHYDROPYRIMIDINE CALCIUM-CHANNEL BLOCKERS - 2-HETEROSUBSTITUTED 4-ARYL-1,4-DIHYDRO-6-METHYL-5-PYRIMIDINECARBOXYLIC ACID-ESTERS AS POTENT MIMICS OF DIHYDROPYRIDINES [J].

ATWAL, KS ;

ROVNYAK, GC ;

SCHWARTZ, J ;

MORELAND, S ;

HEDBERG, A ;

GOUGOUTAS, JZ ;

MALLEY, MF ;

FLOYD, DM .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (05) :1510-1515

[4] Regioselective N-9 arylation of purines employing arylboronic acids in the presence of Cu(II) [J].

Bakkestuen, AK ;

Gundersen, LL .

TETRAHEDRON LETTERS, 2003, 44 (16) :3359-3362

[5] Solid supported aryl/heteroaryl C-N cross-coupling reactions. [J].

Combs, AP ;

Saubern, S ;

Rafalski, M ;

Lam, PYS .

TETRAHEDRON LETTERS, 1999, 40 (09) :1623-1626

[6] Inhibition of hepatitis B virus replication by drug-induced depletion of nucleocapsids [J].

Deres, K ;

Schröder, CH ;

Paessens, A ;

Goldmann, S ;

Hacker, HJ ;

Weber, O ;

Krämer, T ;

Niewöhner, U ;

Pleiss, U ;

Stoltefuss, J ;

Graef, E ;

Koletzki, D ;

Masantschek, RNA ;

Reimann, A ;

Jaeger, R ;

Gross, R ;

Beckermann, B ;

Schlemmer, KH ;

Haebich, D ;

Rübsamen-Waigmann, H .

SCIENCE, 2003, 299 (5608) :893-896

[7]

DIEDRICH F, 1998, METAL CATALYZED CROS

[8] Improved synthesis and preparative scale resolution of racemic monastrol [J].

Dondoni, A ;

Massi, A ;

Sabbatini, S .

TETRAHEDRON LETTERS, 2002, 43 (34) :5913-5916

[9] Heteroaromatic thioether-organostannane cross-coupling [J].

Egi, M ;

Liebeskind, LS .

ORGANIC LETTERS, 2003, 5 (06) :801-802

[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

← 1 2 3 4 →