Amination of Benzoxazoles and 1,3,4-Oxadiazoles Using 2,2,6,6-Tetramethylpiperidine-N-oxoammonium Tetrafluoroborate as an Organic Oxidant

被引：100

作者：

Wertz, Sebastian ^{[1
]}

Kodama, Shintaro ^{[1
]}

Studer, Armido ^{[1
]}

机构：

[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 48期

关键词：

amination; heterocycles; homogeneous catalysis; metal-free reactions; trifluoromethanesulfonic acid; C-H BONDS; CATALYZED DIRECT AMINATION; SCANDIUM TRIFLATE; DIRECT ALKYLATION; SECONDARY-AMINES; PALLADIUM; AZOLES; OXIDATIONS; ARYLATION; ALDEHYDES;

D O I：

10.1002/anie.201104735

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

No transition metals are necessary to convert benzoxazoles and 1,3,4-oxadiazoles into the corresponding pharmacologically interesting 2-aminated heterocycles by formal direct C(2)-amination using tetramethylpiperidine-N-oxoammonium tetrafluoroborate (TEMPO +BF 4 -) as an oxidant (see scheme; TEMP=2,2,6,6- tetramethylpiperidine; TfOH=trifluoromethanesulfonic acid). © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：11511 / 11515

页数：5

共 88 条

[1]

Ackermann L, 2011, ANGEW CHEM, V123, P3926

[2]

Ackermann L., 2009, ANGEW CHEM, V121, P9976, DOI DOI 10.1002/ANGE.200902996

[3] Transition-Metal-Catalyzed Carboxylation of C-H Bonds [J].

Ackermann, Lutz .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (17) :3842-3844

[4] Palladium-Catalyzed Direct Arylations, Alkenylations, and Benzylations through C-H Bond Cleavages with Sulfamates or Phosphates as Electrophiles [J].

Ackermann, Lutz ;

Barfuesser, Sebastian ;

Pospech, Jola .

ORGANIC LETTERS, 2010, 12 (04) :724-726

[5] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Kapdi, Anant R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826

[6] Synthetic applications of nonmetal catalysts for homogeneous oxidations [J].

Adam, W ;

Saha-Möller, CR ;

Ganeshpure, PA .

CHEMICAL REVIEWS, 2001, 101 (11) :3499-3548

[7] A domino copper-catalyzed C-N and C-O cross-coupling for the conversion of primary amides into benzoxazoles [J].

Altenhoff, G ;

Glorius, F .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1661-1664

[8]

[Anonymous], 2009, AM ETHNOL, DOI DOI 10.1002/ANGE.200900413

[9]

[Anonymous], 2011, ANGEW CHEM INT EDIT

[10]

ARMAREGO LF, 2009, PURIFICATION LAB CHE, P274

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