RuCl3-promoted amide formation from azides and thioacids

被引：53

作者：

Fazio, F

Wong, CH

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 51期

关键词：

ruthenium trichloride; amide formation; thioacids; azides;

D O I：

10.1016/j.tetlet.2003.10.054

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Described here is the Ru(III)-promoted amide formation from azides and thioacids, which were shown not to form amides at room temperature in the absence of ruthenium. We believe that a complex formed by Ru(III) increases the reactivity of the thiocarbonyl species and therefore reaction with azides occurs at room temperature, even when less reactive (electron rich and/or sterically hindered) azides are employed. (C) 2003 Published by Elsevier Ltd.

引用

收藏

页码：9083 / 9085

页数：3

相关论文

共 11 条

[1] Metal catalyzed diazo transfer for the synthesis of azides from amines [J].

Alper, PB ;

Hung, SC ;

Wong, CH .

TETRAHEDRON LETTERS, 1996, 37 (34) :6029-6032

[2] A quick diversity-oriented amide-forming reaction to optimize P-subsite residues of HIV protease inhibitors [J].

Brik, A ;

Lin, YC ;

Elder, J ;

Wong, CH .

CHEMISTRY & BIOLOGY, 2002, 9 (08) :891-896

[3] Synthesis of sugar arrays in microtiter plate [J].

Fazio, F ;

Bryan, MC ;

Blixt, O ;

Paulson, JC ;

Wong, CH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (48) :14397-14402

[4] Asymmetric 1,3-dipolar cycloaddition reactions [J].

Gothelf, KV ;

Jorgensen, KA .

CHEMICAL REVIEWS, 1998, 98 (02) :863-909

[5] The chemistry of amine-azide interconversion: Catalytic diazotransfer and regioselective azide reduction [J].

Nyffeler, PT ;

Liang, CH ;

Koeller, KM ;

Wong, CH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (36) :10773-10778

[6] A CONVENIENT AND HIGHLY CHEMOSELECTIVE METHOD FOR THE REDUCTIVE ACETYLATION OF AZIDES [J].

ROSEN, T ;

LICO, IM ;

CHU, DTW .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (07) :1580-1582

[7]

Rostovtsev VV, 2002, ANGEW CHEM INT EDIT, V41, P2596, DOI 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO

[8]

2-4

[9] The coordination chemistry of the C=S function, part XVII. Stereoselective addition reactions of ruthenium thioaldehyde complexes [J].

Schenk, WA .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 661 (1-2) :129-136

[10] The reaction of thio acids with azides: A new mechanism and new synthetic applications [J].

Shangguan, N ;

Katukojvala, S ;

Greenburg, R ;

Williams, LJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (26) :7754-7755