Direct Access to N-Alkylsulfoximines from Sulfides by a Sequential Imidation/Oxidation Procedure

被引:25
作者
Dannenberg, Carl Albrecht [1 ]
Bizet, Vincent [1 ]
Bolm, Carsten [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
来源
SYNTHESIS-STUTTGART | 2015年 / 47卷 / 13期
关键词
sulfoximine; imidation; oxidation; synthetic method; sulfide; SULFOXIMINES SYNTHESES; SYNTHETIC APPLICATIONS; MEDICINAL CHEMISTRY; NITRENE TRANSFER; ALKYLATION; MECHANISM; SULFILIMINES; SULFIMIDES; INHIBITOR; NITROGEN;
D O I
10.1055/s-0034-1380536
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学];
摘要
Synthetically relevant N-alkyl-substituted sulfoximines are directly prepared from sulfides by an unprecedented one-pot imidation/oxidation sequence. In situ generated N-bromoalkylamines serve as readily accessible imidating agents leading to N-alkylsulfiliminium bromides that are subsequently oxidized providing the corresponding N-alkylsulfoximines. In this manner, gram quantities of the products can be obtained in a short period of time avoiding the use of toxic and cumbersome to handle alkylating reagents.
引用
收藏
页码:1951 / 1959
页数:9
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共 50 条
[1]
[Anonymous], 2013, ANGEW CHEM, V125, P9570, DOI DOI 10.1002/EJOC.201501611
[2]
Biological characterization of sulfoxaflor, a novel insecticide [J].
Babcock, Jonathan M. ;
Gerwick, Clifford B. ;
Huang, Jim X. ;
Loso, Michael R. ;
Nakamura, Genta ;
Nolting, Steven P. ;
Rogers, Richard B. ;
Sparks, Thomas C. ;
Thomas, James ;
Watson, Gerald B. ;
Zhu, Yuanming .
PEST MANAGEMENT SCIENCE, 2011, 67 (03) :328-334
[3]
Bizet V., 2014, ANGEW CHEM, V126, P5745
[4]
Light-Induced Ruthenium-Catalyzed Nitrene Transfer Reactions: A Photochemical Approach towards N-Acyl Sulfimides and Sulfoximines [J].
Bizet, Vincent ;
Buglioni, Laura ;
Bolm, Carsten .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (22) :5639-5642
[5]
Fluorinated sulfoximines: syntheses, properties and applications [J].
Bizet, Vincent ;
Kowalczyk, Rafal ;
Bolm, Carsten .
CHEMICAL SOCIETY REVIEWS, 2014, 43 (08) :2426-2438
[6]
Bolm C, 2002, SYNTHESIS-STUTTGART, P879
[7]
Bolm C., 2007, ASYMMETRIC SYNTHESIS, P149, DOI DOI 10.1002/9783527610648.CH2A
[8]
Bolm C., 2012, J CHEM, P49
[9]
ELECTROPHILIC BROMINATION OF GASEOUS AROMATIC-COMPOUNDS - MECHANISM AND LINEAR FREE-ENERGY EFFECTS ON REACTION-RATES [J].
BORTOLINI, O ;
YANG, SS ;
COOKS, RG .
ORGANIC MASS SPECTROMETRY, 1993, 28 (11) :1313-1322
[10]
Synthesis and Structural Characterization of Molybdenum(VI) and Iron(II) Coordination Compounds with S-Alkyl-N-methyl-S-(2-pyridyl)sulfoximines and Catalytic Epoxidation Activity of the Molybdenum Complexes [J].
Brussaard, Yvonne ;
Olbrich, Falk ;
Schaumann, Ernst .
INORGANIC CHEMISTRY, 2013, 52 (22) :13160-13166