Palladium(0)-Catalyzed, Copper(I)-Mediated Coupling of Cyclic Thioamides with Alkenylboronic Acids, Organostannanes, and Siloxanes

被引：34

作者：

Arshad, Nuzhat

Hashim, Jamshed

Kappe, C. Oliver ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 14期

关键词：

CARBON-CARBON; BORONIC ACIDS; THIOETHERS; CHEMISTRY; KETONES; STILLE;

D O I：

10.1021/jo900848s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Pd-catalyzed cross-coupling of cyclic thioamides and thioureas with alkenylboronic acids, vinyl- and (het)aryl-stannanes, and arylsiloxanes in the presence of stoichiometric amounts of a Cu(I) cofactor is described. The desulfitative C-C cross-coupling protocol of the Liebeskind-Srogl type is performed under neutral conditions and can be applied to a range of heterocyclic structures with embedded thioamide fragments. Employing controlled microwave irradiation at 100 degrees C utilizing either a single-mode reactor or a multimode parallel reaction platform, cross-couplings can generally be completed within 1-3 h and proceed in good yields.

引用

收藏

页码：5118 / 5121

页数：4

相关论文

共 28 条

[1] Selective cross-couplings. Sequential Stille-Liebeskind/Srogl reactions of 3-chloro-4-arylthiocyclobutene-1 2-dione [J].

Aguilar-Aguilar, Angelica ;

Pena-Cabrera, Eduardo .

ORGANIC LETTERS, 2007, 9 (21) :4163-4166

[2] 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

[3] High-Throughput Experimentation Platform: Parallel Microwave Chemistry in HPLC/GC Vials [J].

Damm, Markus ;

Kappe, C. Oliver .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2009, 11 (03) :460-468

[4]

Denmark SE, 2003, ALDRICHIM ACTA, V36, P75

[5] 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

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

Egi, M ;

Liebeskind, LS .

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

[7] How I came across the silicon-based cross-coupling reaction [J].

Hiyama, T .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 653 (1-2) :58-61

[8] Controlled microwave heating in modern organic synthesis [J].

Kappe, CO .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (46) :6250-6284

[9] Switchable catalysis: Modular synthesis of functionalized pyrimidinones via selective sulfide and halide cross-coupling chemistry [J].

Kusturin, C ;

Liebeskind, LS ;

Rahman, H ;

Sample, K ;

Schweitzer, B ;

Srogl, J ;

Neumann, WL .

ORGANIC LETTERS, 2003, 5 (23) :4349-4352

[10] A new catalytic cross-coupling approach for the synthesis of protected aryl and heteroaryl amidines [J].

Kusturin, CL ;

Liebeskind, LS ;

Neumann, WL .

ORGANIC LETTERS, 2002, 4 (06) :983-985