Palladium-Catalyzed Double Carbonylation Using Near Stoichiometric Carbon Monoxide: Expedient Access to Substituted 13C2-Labeled Phenethylamines

被引：68

作者：

Nielsen, Dennis U.

Neumann, Karoline

Taaning, Rolf H.

Lindhardt, Anders T.

Modvig, Amalie

Skrydstrup, Troels ^{[1
]}

机构：

[1] Aarhus Univ, Ctr Insoluble Prot Struct InSPIN, Dept Chem, Langelandsgade 140, DK-8000 Aarhus C, Denmark

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 14期

基金：

新加坡国家研究基金会;

关键词：

POLYCYCLIC AROMATIC-HYDROCARBONS; INTERNAL STANDARDS; ACID-DERIVATIVES; EX-SITU; EFFICIENT; AMIDES; DRUGS; SPECTROMETRY; MECHANISMS; INHIBITOR;

D O I：

10.1021/jo3009337

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and general approach for C-13(2)- and H-2-labeled phenethylamine derivatives has been developed, based on a highly convergent single-step assembly of the carbon skeleton. The efficient incorporation of two carbon-13 isotopes into phenethylamines was accomplished using a palladium-catalyzed double carbonylation of aryl iodides with near stoichiometric carbon monoxide.

引用

页码：6155 / 6165

页数：11

共 64 条

[1]

ANDREWS BD, 1969, TETRAHEDRON LETT, P1859

[2]

Anturia A.G., 2010, ANALYST, V135, P953

[3] Reaction diastereoselectivity of chiral aminoalcohols/[Co(II)NO3]+ complexes in evaporating ESI nanodroplets: new insights from a joint experimental and computational investigation [J].

Aschi, Massimiliano ;

Fraschetti, Caterina ;

Filippi, Antonello ;

Speranza, Maurizio .

JOURNAL OF MASS SPECTROMETRY, 2009, 44 (07) :1038-1046

[4] PHENOL OXIDATION AND BIOSYNTHESIS .26. ISONITRILES IN THE SYNTHESIS OF BENZYLISOQUINOLINE DERIVATIVES [J].

BARRETT, AGM ;

BARTON, DHR ;

FALCK, JR ;

PAPAIOANNOU, D ;

WIDDOWSON, DA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (03) :652-661

[5] Palladium-Catalyzed N-Acylation of Monosubstituted Ureas Using Near-Stoichiometric Carbon Monoxide [J].

Bjerglund, Klaus ;

Lindhardt, Anders T. ;

Skrydstrup, Troels .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (08) :3793-3799

[6] Zinc Chloride Promoted Formal Oxidative Coupling of Aromatic Aldehydes and Isocyanides to α-Ketoamides [J].

Bouma, Marinus ;

Masson, Geraldine ;

Zhu, Jieping .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (08) :2748-2751

[7] Heavier Alkaline Earth Catalysts for the Intermolecular Hydroamination of Vinylarenes, Dienes, and Alkynes [J].

Brinkmann, Christine ;

Barrett, Anthony G. M. ;

Hill, Michael S. ;

Procopiou, Panayiotis A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (04) :2193-2207

[8]

CAMPAIGNE E, 1973, Synthetic Communications, V3, P325, DOI 10.1080/00397917308063484

[9] Asymmetric aerobic oxidation of α-hydroxy acid derivatives by c4-symmetric, vanadate-centered, Tetrakisvanadyl(V) clusters derived from N-salicylidene-α-aminocarboxylates [J].

Chen, Chien-Tien ;

Bettigeri, Sampada ;

Weng, Shiue-Shien ;

Pawar, Vijay D. ;

Lin, Ya-Hui ;

Liu, Cheng-Yuan ;

Lee, Way-Zen .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (22) :8175-8185

[10] Copper-Catalyzed Synthesis of Azaspirocyclohexadienones from α-Azido-N-arylamides under an Oxygen Atmosphere [J].

Chiba, Shunsuke ;

Zhang, Line ;

Lee, Jian-Yuan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (21) :7266-+

← 1 2 3 4 5 6 7 →