Silver-Mediated Direct Amination of Benzoxazoles: Tuning the Amino Group Source from Formamides to Parent Amines

被引：273

作者：

Cho, Seung Hwan ^{[1
]}

Kim, Ji Young ^{[1
]}

Lee, S. Yunmi ^{[1
]}

Chang, Sukbok ^{[1
]}

机构：

[1] Korea Adv Inst Sci & Technol, Taejon 305701, South Korea

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 48期

关键词：

amination; benzoxazoles; C-N coupling; formamides; silver; C-H BONDS; INTERMOLECULAR AMINATION; DIRECT ARYLATION; ARYL; FUNCTIONALIZATION; ALKENES; AMINOCARBONYLATION; HYDROAMINATION; AMIDATION; CLEAVAGE;

D O I：

10.1002/anie.200903957

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Formamides or parent amines were used as an amino group source for the silver-mediated amination of benzoxazoles. Although reactions with formamides proceeded at high temperatures, the direct amination with amines took place under much milder conditions (see scheme). Optically active amino groups could also be installed without racemization. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：9127 / 9130

页数：4

共 51 条

[1] Palladium-Catalyzed Direct Arylations of Heteroarenes with Tosylates and Mesylates [J].

Ackermann, Lutz ;

Althammer, Andreas ;

Fenner, Sabine .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (01) :201-204

[2] Synthesis, characterization and anti-HIV and antitumor activities of new coumarin derivatives [J].

Al-Soud, Yaseen A. ;

Al-Sa'doni, Haitham H. ;

Amajaour, Houssain A. S. ;

Salih, Kifah S. M. ;

Mubarak, Mohammad S. ;

Al-Masoudi, Najim A. ;

Jaber, Ihsan H. .

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2008, 63 (01) :83-89

[3] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[4] Silver-mediated synthesis of heterocycles [J].

Alvarez-Corral, Miriam ;

Munoz-Dorado, Manuel ;

Rodirguez-Garcia, Ignacio .

CHEMICAL REVIEWS, 2008, 108 (08) :3174-3198

[5]

[Anonymous], 2009, ANGEW CHEM-GER EDIT

[6] Aerobic oxidative amination of unactivated alkenes catalyzed by palladium [J].

Brice, JL ;

Harang, JE ;

Timokhin, VI ;

Anastasi, NR ;

Stahl, SS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (09) :2868-2869

[7] C2, C5, and C4 azole N-oxide direct arylation including room-temperature reactions [J].

Campeau, Louis-Charles ;

Bertrand-Laperle, Megan ;

Leclerc, Jean-Philippe ;

Villemure, Elisia ;

Gorelsky, Serge ;

Fagnou, Keith .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) :3276-+

[8] 1,3-diol synthesis via controlled, radical-mediated C-H functionalization [J].

Chen, Ke ;

Richter, Jeremy M. ;

Baran, Phil S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (23) :7247-+

[9] Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant [J].

Chen, Xiao ;

Hao, Xue-Shi ;

Goodhue, Charles E. ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6790-6791

[10]

Chen Y.X., 2008, Angewandte Chemie, V120, P9470

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