Microwave-assisted, Mo(CO)6-mediated, palladium-catalyzed amino-carbonylation of aryl halides using allylamine:: from exploration to scale-up

被引：34

作者：

Appukkuttan, Prasad ^{[1
]}

Axelsson, Linda ^{[1
]}

Van der Eycken, Erik ^{[2
]}

Larhed, Mats ^{[1
]}

机构：

[1] Uppsala Univ, Dept Med Chem, Uppsala Biomed Ctr, SE-75123 Uppsala, Sweden

[2] Katholieke Univ Leuven, LOMAC, Dept Chem, B-3001 Louvain, Belgium

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 39期

基金：

瑞典研究理事会;

关键词：

carbonylation; microwave; palladium; aryl chloride; scale-up;

D O I：

10.1016/j.tetlet.2008.07.053

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium-catalyzed aminocarbonylations of various (hetero)aryl halides with allylamine using Mo(CO)(6) as a solid, in situ CO source, were explored. Microwave-enhanced conditions proved to be highly useful in promoting the conversions in a mere 10-20 min with various (hetero)aryl iodides, bromides and chlorides. The scale-up of a microwave-enhanced aminocarbonylation to 25 mmol scale was performed successfully. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：5625 / 5628

页数：4

共 36 条

[1] The heck reaction as a sharpening stone of palladium catalysis [J].

Beletskaya, IP ;

Cheprakov, AV .

CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066

[2] PROGRESS IN HYDROFORMYLATION AND CARBONYLATION [J].

BELLER, M ;

CORNILS, B ;

FROHNING, CD ;

KOHLPAINTNER, CW .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1995, 104 (01) :17-85

[3] CHELATE-ASSISTED, PD-CATALYZED EFFICIENT CARBONYLATION OF ARYL CHLORIDES [J].

BENDAVID, Y ;

PORTNOY, M ;

MILSTEIN, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (23) :8742-8744

[4] Industrial R&D on catalytic C-C and C-N coupling reactions: A personal account on goals, approaches and results [J].

Blaser, HU ;

Indolese, A ;

Naud, F ;

Nettekoven, U ;

Schnyder, A .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1583-1598

[5] Pd-benzothiazole carbene catalysed carbonylation of aryl halides in ionic liquids [J].

Calò, V ;

Giannoccaro, P ;

Nacci, A ;

Monopoli, A .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 645 (1-2) :152-157

[6] PALLADIUM-CATALYZED CARBONYLATION OF IODOARENES IN AQUEOUS SOLUBILIZED SYSTEMS [J].

CHEPRAKOV, AV ;

PONOMAREVA, NV ;

BELETSKAYA, IP .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 486 (1-2) :297-300

[7] Rapid palladium-catalyzed synthesis of esters from aryl halides utilizing Mo(CO)6 as a solid carbon monoxide source [J].

Georgsson, J ;

Hallberg, A ;

Larhed, M .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2003, 5 (04) :350-352

[8] Palladium catalysed cascade cyclisation-anion capture, relay switches and molecular queues [J].

Grigg, R ;

Sridharan, V .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :65-87

[9] Olefin metathesis [J].

Grubbs, RH .

TETRAHEDRON, 2004, 60 (34) :7117-7140

[10] Application of palladacycles in Heck type reactions [J].

Herrmann, WA ;

Böhm, VPW ;

Reisinger, CP .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :23-41

← 1 2 3 4 →