Transition-Metal-Free Oxidative Iodination of 1,3,4-Oxadiazoles

被引：10

作者：

Dannenberg, Carl Albrecht ^{[1
]}

Bizet, Vincent ^{[1
]}

Zou, Liang-Hua ^{[1
]}

Bolm, Carsten ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 2015卷 / 01期

关键词：

Synthetic methods; Iodine; Oxidation; Nitrogen heterocycles; Oxadiazoles; AROMATIC-COMPOUNDS; ELECTROPHILIC IODINATION; DIRECT ARYLATION; DERIVATIVES; ARENES; IODINE;

D O I：

10.1002/ejoc.201403352

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Transition-metal-free oxidative iodination of 2-substituted 1,3,4-oxadiazoles was achieved by using sodium iodide as the halide source and Selectfluor as the oxidant. Variously substituted products were obtained in moderate to good yields under operationally straightforward conditions. Compared to existing methods for analogous conversions, the newly developed protocol appears synthetically attractive.

引用

页码：77 / 80

页数：4

共 53 条

[1]

[Anonymous], 2007, ANGEW CHEM

[2] C-N bond forming cross-coupling reactions: an overview [J].

Bariwal, Jitender ;

Van der Eycken, Erik .

CHEMICAL SOCIETY REVIEWS, 2013, 42 (24) :9283-9303

[3] ACID-MEDIATED REACTION OF BIS(PYRIDINE)IODONIUM(I) TETRAFLUOROBORATE WITH AROMATIC-COMPOUNDS - A SELECTIVE AND GENERAL IODINATION METHOD [J].

BARLUENGA, J ;

GONZALEZ, JM ;

GARCIAMARTIN, MA ;

CAMPOS, PJ ;

ASENSIO, G .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (08) :2058-2060

[4] Iodine(I) Reagents in Hydrochloric Acid-Catalyzed Oxidative Iodination of Aromatic Compounds by Hydrogen Peroxide and Iodine [J].

Bedrac, Leon ;

Iskra, Jernej .

ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (07) :1243-1248

[5] Nuclear fluorination of 2,4-diarylthiazoles with Accufluor® [J].

Campbell, Timmeda F. ;

Stephens, Chad E. .

JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (12) :1591-1594

[6] N-aryl pyrazoles: DFT calculations of CH acidity and deprotonative metallation using a combination of lithium and zinc amides [J].

Chevallier, Floris ;

Halauko, Yury S. ;

Pecceu, Christelle ;

Nassar, Ibrahim F. ;

Dam, To Uyen ;

Roisnel, Thierry ;

Matulis, Vadim E. ;

Ivashkevich, Oleg A. ;

Mongin, Florence .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (12) :4671-4684

[7] Process Development and Multikilogram-Scale Synthesis of a TRPV1 Antagonist [J].

Cleator, Ed ;

Scott, Jeremy P. ;

Avalle, Paulo ;

Bio, Matthew M. ;

Brewer, Sarah E. ;

Davies, Antony J. ;

Gibb, Andrew D. ;

Sheen, Faye J. ;

Stewart, Gavin W. ;

Wallace, Debra J. ;

Wilson, Robert D. .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2013, 17 (12) :1561-1567

[8] Deprotonative metallation of ferrocenes using mixed lithium-zinc and lithium-cadmium combinations [J].

Dayaker, Gandrath ;

Sreeshailam, Aare ;

Chevallier, Floris ;

Roisnel, Thierry ;

Krishna, Palakodety Radha ;

Mongin, Florence .

CHEMICAL COMMUNICATIONS, 2010, 46 (16) :2862-2864

[9] Superior reactivity of thiosemicarbazides in the synthesis of 2-amino-1,3,4-oxadiazoles [J].

Dolman, Sarah J. ;

Gosselin, Francis ;

O'Shea, Paul D. ;

Davies, Ian W. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (25) :9548-9551

[10] Bystanding F+ Oxidants Enable Selective Reductive Elimination from High-Valent Metal Centers in Catalysis [J].

Engle, Keary M. ;

Mei, Tian-Sheng ;

Wang, Xisheng ;

Yu, Jin-Quan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (07) :1478-1491

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