Selenium-catalyzed oxidative halogenation

被引:43
作者
Mellegaard-Waetzig, Shelli R. [1 ]
Wang, Chao [1 ]
Tunge, Jon A. [1 ]
机构
[1] Univ Kansas, Dept Chem, Lawrence, KS 66045 USA
关键词
D O I
10.1016/j.tet.2005.12.072
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Organoselenides catalyze the oxidation of halides by H2O2. Furthermore, these selenides catalyze the transfer of oxidized halogens from N-halosuccinimides to olefins and ketones. Thus, organoselenides catalyze oxidative halogenation reactions including halolactonization, alpha-halogenation of ketones, and allylic halogenation. The ability of selenium to undergo reversible 2e(-) oxidation-reduction chemistry facilitates halogenation through selenium-bound halogen intermediates. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7191 / 7198
页数:8
相关论文
共 40 条
[11]  
FAULKNER DJ, 1992, OCEANUS, P29
[12]  
Gamble SC, 1997, J CHEM TECHNOL BIOT, V68, P123
[13]  
GOLDSMITH D, 1979, TETRAHEDRON LETT, V50, P4801
[14]   SOLENOLIDES, NEW ANTIINFLAMMATORY AND ANTIVIRAL DITERPENOIDS FROM A MARINE OCTOCORAL OF THE GENUS SOLENOPODIUM [J].
GROWEISS, A ;
LOOK, SA ;
FENICAL, W .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (11) :2401-2406
[15]  
Higgs DE, 2001, ORG LETT, V3, P349
[16]   SELENIUM-CATALYZED NONRADICAL CHLORINATION OF OLEFINS WITH N-CHLOROSUCCINIMIDE [J].
HORI, T ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (23) :4204-4208
[17]   CONVERSION OF ALLYLIC PHENYLSELENIDES TO THE REARRANGED ALLYLIC CHLORIDES BY N-CHLOROSUCCINIMIDE - MECHANISM OF SELENIUM-CATALYZED ALLYLIC CHLORINATION OF BETA-PINENE [J].
HORI, T ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (23) :4208-4210
[18]   SUBSTRATE-SPECIFICITY, REGIOSPECIFICITY AND STEREOSPECIFICITY OF HALOGENATION REACTIONS CATALYZED BY NON-HEME-TYPE BROMOPEROXIDASE OF CORALLINA-PILULIFERA [J].
ITOH, N ;
HASAN, AKMQ ;
IZUMI, Y ;
YAMADA, H .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1988, 172 (02) :477-484
[19]   A MODEL STUDY ON THE EFFECT OF AN AMINO GROUP ON THE ANTIOXIDANT ACTIVITY OF GLUTATHIONE-PEROXIDASE [J].
IWAOKA, M ;
TOMODA, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (06) :2557-2561
[20]   STEROIDAL SELENOXIDES DIASTEREOISOMERIC AT SELENIUM . SYN-ELIMINATION, ABSOLUTE CONFIGURATION, AND OPTICAL ROTATORY DISPERSION CHARACTERISTICS [J].
JONES, DN ;
MUNDY, D ;
WHITEHOUSE, RD .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1970, (02) :86-+