Transannulation of 1-Sulfonyl-1,2,3-triazoles with Heterocumulenes

被引：207

作者：

Chuprakov, Stepan ^{[1
]}

Kwok, Sen Wai ^{[1
]}

Fokin, Valery V. ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 12期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

RHODIUM(II) AZAVINYL CARBENES; RH-CATALYZED TRANSANNULATION; H INSERTION REACTIONS; TERMINAL ALKYNES; REACTIVITY; N-SULFONYL-1,2,3-TRIAZOLES; CYCLOPROPANATION; 1,2,3-TRIAZOLES; REARRANGEMENTS; DIRHODIUM(II);

D O I：

10.1021/ja400350c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Readily available 1-mesyl-1,2,3-triazoles are efficiently converted into a variety of imidazolones and thiazoles by Rh(II)-catalyzed denitrogenative reactions with isocyanates and isothiocyanates, respectively. The proposed triazole-diazoimine equilibrium results in the formation of highly reactive azavinyl metal-carbenes, which react with heterocumulenes causing an apparent swap of 1,2,3-triazole core for another heterocycle.

引用

页码：4652 / 4655

页数：4

共 31 条

[21] Selectivity enhancement in the Rh(II)-Catalyzed cyclopropanation of styrene with (Silanyloxyvinyl)diazoacetates [J].

Muller, P ;

Bernardinelli, G ;

Allenbach, YF ;

Ferri, M ;

Flack, HD .

ORGANIC LETTERS, 2004, 6 (11) :1725-1728

[22] Rhodium(II)-catalyzed olefin cyclopropanation with the phenyliodonium ylide derived from Meldrum's acid [J].

Müller, P ;

Allenbach, Y ;

Robert, E .

TETRAHEDRON-ASYMMETRY, 2003, 14 (07) :779-785

[23] Efficient Synthesis of 1-Sulfonyl-1,2,3-triazoles [J].

Raushel, Jessica ;

Fokin, Valery V. .

ORGANIC LETTERS, 2010, 12 (21) :4952-4955

[24] Ring Expansion and Rearrangements of Rhodium(II) Azavinyl Carbenes [J].

Selander, Nicklas ;

Worrell, Brady T. ;

Fokin, Valery V. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (52) :13054-13057

[25] Arylation of Rhodium(II) Azavinyl Carbenes with Boronic Acids [J].

Selander, Nicklas ;

Worrell, Brady T. ;

Chuprakov, Stepan ;

Velaparthi, Subash ;

Fokin, Valery V. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (36) :14670-14673

[26] Rhodium(II)-Catalyzed Asymmetric Sulfur(VI) Reduction of Diazo Sulfonylamidines [J].

Selander, Nicklas ;

Fokin, Valery V. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (05) :2477-2480

[27] Practical synthesis of dirhodium(II) Tetrakis[N-phthaloyl-(S)-tert-leucinate] [J].

Tsutsui, H ;

Abe, T ;

Nakamura, S ;

Anada, M ;

Hashimoto, S .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2005, 53 (10) :1366-1368

[28]

Wuts P. G. M., 2007, PROTECTIVE GROUPS OR, P872

[29] Copper-catalyzed synthesis of N-sulfonyl-1,2,3-triazoles:: Controlling selectivity [J].

Yoo, Eun Jeong ;

Ahlquist, Marten ;

Kim, Seok Hwan ;

Bae, Imhyuck ;

Fokin, Valery V. ;

Sharpless, K. Barry ;

Chang, Sukbok .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) :1730-1733

[30] Sulfonyl-1,2,3-Triazoles: Convenient Synthones for Heterocyclic Compounds [J].

Zibinsky, Mikhail ;

Fokin, Valery V. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (05) :1507-1510

← 1 2 3 4 →