Synthesis of γ-halogenated ketones via the Ce(IV)-mediated oxidative coupling of cyclobutanols and inorganic halides

被引：42

作者：

Casey, Brian M. ^{[1
]}

Eakin, Cynthia A. ^{[1
]}

Flowers, Robert A., II ^{[1
]}

机构：

[1] Lehigh Univ, Dept Chem, Bethlehem, PA 18015 USA

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 12期

基金：

美国国家卫生研究院;

关键词：

CAN; Cyclobutanol; gamma-Substituted ketone; Oxidative coupling; CERIUM(IV) AMMONIUM-NITRATE; SOLVENT-DEPENDENT CHEMOSELECTIVITIES; RADICAL-CATION; ALKYL-HALIDES; EFFICIENT;

D O I：

10.1016/j.tetlet.2008.12.114

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A straightforward method for the synthesis of gamma-halo-substituted ketones formed via the CAN-initiated oxidative addition of halides to 1-substituted cyclobutanols has been developed. This method has short reaction times, and provides access to a range of bromo and iodo gamma-substituted ketones in good to excellent yields. (C) 2009 Elsevier Ltd. All rights reserved.

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页码：1264 / 1266

页数：3

相关论文

共 22 条

[1] 1,2-HYDROGEN MIGRATION AND ALKENE FORMATION IN THE PHOTOEXCITED STATES OF ALKYLPHENYLDIAZOMETHANES [J].

CELEBI, S ;

LEYVA, S ;

MODARELLI, DA ;

PLATZ, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (19) :8613-8620

[2] Synthesis and SAR investigations for novel melanin-concentrating hormone 1 receptor (MCH1) antagonists part 2:: A hybrid strategy combining key fragments of HTS hits [J].

Chen, Chien-An ;

Jiang, Yu ;

Lu, Kai ;

Daniewska, Irena ;

Mazza, Christine G. ;

Negron, Leonardo ;

Forray, Carlos ;

Parola, Tony ;

Li, Boshan ;

Hegde, Laxminarayan G. ;

Wolinsky, Toni D. ;

Craig, Douglas A. ;

Kong, Ron ;

Wetzel, John M. ;

Andersen, Kim ;

Marzabadi, Mohammad R. .

JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (16) :3883-3890

[3] ELECTRICAL EFFECTS OF CYCLOALKYL GROUPS [J].

HAHN, RC ;

CORBIN, TF ;

SHECHTER, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (13) :3404-&

[4] Direct oxidative conversion of alkyl halides into nitriles with molecular iodine in aqueous ammonia [J].

Iida, Shinpei ;

Togo, Hideo .

SYNLETT, 2008, (11) :1639-1642

[5] COMBINED ANALGESIC NEUROLEPTIC ACTIVITY IN N-BUTYROPHENONE PRODINE-LIKE COMPOUNDS [J].

IORIO, MA ;

REYMER, TP ;

FRIGENI, V .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (10) :1906-1910

[6]

Jahn U, 2001, EUR J ORG CHEM, V2001, P3333

[7] Mechanistic studies of Ce(IV)-mediated oxidation of β-dicarbonyls:: Solvent-dependent behavior of radical cation intermediates [J].

Jiao, Jingliang ;

Zhang, Yang ;

Devery, James J., III ;

Xu, Luna ;

Deng, Jennifer ;

Flowers, Robert A., II .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (15) :5486-5492

[8] An efficient and general approach to β-functionalized ketones [J].

Jiao, Jingliang ;

Nguyen, Larry X. ;

Patterson, Dennis R. ;

Flowers, Robert A., II .

ORGANIC LETTERS, 2007, 9 (07) :1323-1326

[9] Understanding reactivity patterns of the dialkylaniline radical cation [J].

Kirchgessner, Micha ;

Sreenath, Kesavapillai ;

Gopidas, Karical R. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (26) :9849-9852

[10] APPLICATION OF LANTHANIDE REAGENTS IN ORGANIC-SYNTHESIS [J].

MOLANDER, GA .

CHEMICAL REVIEWS, 1992, 92 (01) :29-68