Copper-Catalyzed Intermolecular Aminooxygenation of Styrenes using N-Fluorobenzenesulfonimide and Simple Alcohols

被引:30
作者
Herrera-Leyton, Camilo [1 ]
Madrid-Rojas, Matias [1 ]
Lopez, Jhon J. [1 ]
Canete, Alvaro [1 ]
Hermosilla-Ibanez, Patricio [2 ,3 ]
Perez, Edwin G. [1 ]
机构
[1] Pontificia Univ Catolica Chile, Dept Organ Chem, Fac Chem, Ave Vicuna Mackenna 4860,Casilla 306,Correo 22, Santiago, Chile
[2] Univ Santiago Chile USA CH, Fac Quim & Biol, Santiago, Chile
[3] CEDENNA, Ctr Desarrollo Nanotecnol, Santiago, Chile
关键词
aminooxygenation; copper; neuronal ligands; radicals; regioselectivity; CARBOXYLIC-ACIDS; BOND FORMATION; ALKENES; OLEFINS; AMINOHYDROXYLATION; OXYAMINATION; DERIVATIVES; AMINOACETOXYLATION; AMINOFLUORINATION; AMINOPALLADATION;
D O I
10.1002/cctc.201600254
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The mild and fast copper-catalyzed radical and regioselective aminoalkoxylation of styrenes by using N-fluorobenzenesulfonimide and simple alcohols as nitrogen and alkoxy sources, respectively, was investigated. The aminoalkoxylated products obtained could be used in the synthesis of new compounds with possible activity as neurotransmitter receptor ligands.
引用
收藏
页码:2015 / 2018
页数:4
相关论文
共 48 条
[1]   1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].
Ager, DJ ;
Prakash, I ;
Schaad, DR .
CHEMICAL REVIEWS, 1996, 96 (02) :835-875
[2]   Aerobic Copper-Catalyzed Organic Reactions [J].
Allen, Scott E. ;
Walvoord, Ryan R. ;
Padilla-Salinas, Rosaura ;
Kozlowski, Marisa C. .
CHEMICAL REVIEWS, 2013, 113 (08) :6234-6458
[3]   Deprotection of sulfonyl aziridines [J].
Alonso, DA ;
Andersson, PG .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) :9455-9461
[4]   Novel 2-(substituted benzyl)quinuclidines inhibit human α7 and α4β2 nicotinic receptors by different mechanisms [J].
Arias, Hugo R. ;
Lopez, Jhon J. ;
Feuerbach, Dominik ;
Fierro, Angelica ;
Ortells, Marcelo O. ;
Perez, Edwin G. .
INTERNATIONAL JOURNAL OF BIOCHEMISTRY & CELL BIOLOGY, 2013, 45 (11) :2420-2430
[5]  
Beaumont S., 2010, Angew. Chem, V122, P1678
[6]   Catalytic Oxyamidation of Indoles [J].
Beaumont, Stephane ;
Pons, Valerie ;
Retailleau, Pascal ;
Dodd, Robert H. ;
Dauban, Philippe .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (09) :1634-1637
[7]   Anionic Halocuprate(II) Complexes as Catalysts for the Oxaziridine-Mediated Aminohydroxylation of Olefins [J].
Benkovics, Tamas ;
Du, Juana ;
Guzei, Ilia A. ;
Yoon, Tehshik P. .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15) :5545-5552
[8]   The synthesis of vicinal amino alcohols [J].
Bergmeier, SC .
TETRAHEDRON, 2000, 56 (17) :2561-2576
[9]   Catalytic Intermolecular Alkene Oxyamination with Nitrenes [J].
Dequirez, Geoffroy ;
Ciesielski, Jennifer ;
Retailleau, Pascal ;
Dauban, Philippe .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (29) :8929-8933
[10]   Recent Developments in Methodology for the Direct Oxyamination of Olefins [J].
Donohoe, Timothy J. ;
Callens, Cedric K. A. ;
Flores, Aida ;
Lacy, Adam R. ;
Rathi, Akshat H. .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (01) :58-76