Aminocarbonylations of alkenyl phosphates, chlorides, bromides, and triflates with Mo(CO)6 as a solid CO source

被引：39

作者：

Lagerlund, Olof ^{[1
]}

Mantel, Mette L. H. ^{[1
]}

Larhed, Mats ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 2009年 / 65卷 / 36期

基金：

瑞典研究理事会;

关键词：

Carbonylation; Microwave; Vinyl halides; Vinyl phosphates; Vinyl triflates; Alkenyl electrophiles; Palladium; Enolizable ketones; PALLADIUM-CATALYZED CARBONYLATION; MICROWAVE-PROMOTED AMINOCARBONYLATION; CARBON-MONOXIDE; ARYL CHLORIDES; CONVENIENT; SCOPE; AMIDATION; COUPLINGS; EXCHANGE; HALIDES;

D O I：

10.1016/j.tet.2009.06.101

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium-catalyzed aminocarbonylations of alkenyl chlorides, bromides, and triflates were investigated using Mo(CO)(6) as a solid carbon monoxide source. The reactions afforded moderate to good yields producing a wide variety of acrylamides after 20 min of microwave irradiation. In addition, the aminocarbonylation reaction was, for the first time, expanded to include alkenyl phosphates as starting materials. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：7646 / 7652

页数：7

共 49 条

[41] Convenient synthesis of substituted piperidinones from α,β-unsaturated amides:: Formal synthesis of deplancheine, tacamonine, and paroxetine [J].

Takasu, K ;

Nishida, N ;

Tomimura, A ;

Ihara, M .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) :3957-3962

[42] Dynamic ligand exchange of the lanthanide complex leading to structural and functional transformation: One-pot sequential catalytic asymmetric epoxidation-regioselective epoxide-opening process [J].

Tosaki, SY ;

Tsuji, R ;

Ohshima, T ;

Shibasaki, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (07) :2147-2155

[43] Dimethylformamide as a carbon monoxide source in fast palladium-catalyzed aminocarbonylations of aryl bromides [J].

Wan, YQ ;

Alterman, M ;

Larhed, M ;

Hallberg, A .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (17) :6232-6235

[44] Increasing rates and scope of reactions: Sluggish amines in microwave-heated aminocarbonylation reactions under air [J].

Wannberg, J ;

Larhed, M .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (14) :5750-5753

[45] Hydroxylamine as an ammonia equivalent in microwave-enhanced aminocarbonylations [J].

Wu, XY ;

Wannberg, J ;

Larhed, M .

TETRAHEDRON, 2006, 62 (19) :4665-4670

[46] Microwave-promoted aminocarbonylation of aryl iodides, aryl bromides, and aryl chlorides in water [J].

Wu, XY ;

Ekegren, JK ;

Larhed, M .

ORGANOMETALLICS, 2006, 25 (06) :1434-1439

[47] Microwave-enhanced aminocarbonylations in water [J].

Wu, XY ;

Larhed, M .

ORGANIC LETTERS, 2005, 7 (15) :3327-3329

[48] Easy-to-execute carbonylations:: Microwave synthesis of acyl sulfonamides using Mo(CO)6 as a solid carbon monoxide source [J].

Wu, XY ;

Rönn, R ;

Gossas, T ;

Larhed, M .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08) :3094-3098

[49] Palladium catalysed regioselective arylation of electron-rich olefins by aryl halides [J].

Xu, LJ ;

Chen, WP ;

Xiao, JL .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 187 (02) :189-193

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