Recent advances in metal-mediated carbon-nitrogen bond formation reactions: Aziridination and amidation

被引：220

作者：

Halfen, JA ^{[1
]}

机构：

[1] Univ Wisconsin, Dept Chem, Eau Claire, WI 54702 USA

来源：

CURRENT ORGANIC CHEMISTRY | 2005年 / 9卷 / 07期

关键词：

D O I：

10.2174/1385272053765024

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This review describes recent progress in the development of homogeneous, metal-mediated, catalytic pathways to synthetically valuable aziridines and sulfonamides. Areas of investigation described within this review include: (a) catalytic copper, iron, and silver-mediated nitrene transfer from the iminoiodinanes to olefins, (b) development of alternative nitrene sources for olefin aziridination, including N-halo-p-toluene sulfonamides, iminoiodinanes featuring labile N-protecting groups, and sulfonylazides, (c) use of single-pot aziridination protocols for the in situ generation of iminoiodinanes, and (d) metal-mediated carbene transfer to imines.

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页码：657 / 669

页数：13

相关论文

共 75 条

[1] A simple copper catalyst for both aziridination of alkenes and amination of activated hydrocarbons with chloramine-T trihydrate [J].

Albone, DP ;

Aujla, PS ;

Taylor, PC ;

Challenger, S ;

Derrick, AM .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) :9569-9571

[2] Deprotection of sulfonyl aziridines [J].

Alonso, DA ;

Andersson, PG .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) :9455-9461

[3] Cu(I) β-diketiminates for alkene aziridination:: Reversible Cu-arene binding and catalytic nitrene transfer from Phl=NTs [J].

Amisial, LD ;

Dai, XL ;

Kinney, RA ;

Krishnaswamy, A ;

Warren, TH .

INORGANIC CHEMISTRY, 2004, 43 (21) :6537-6539

[4] Palladium(II)-promoted aziridination of olefins with bromamine T as the nitrogen transfer reagent [J].

Antunes, AMM ;

Marto, SJL ;

Branco, PS ;

Prabhakar, S ;

Lobo, AM .

CHEMICAL COMMUNICATIONS, 2001, (05) :405-406

[5] Aminative rearrangement of 2-alkoxy-3,4-dihydro-2H-pyrans:: a novel stereocontrolled route to substituted pyrrolidines [J].

Armstrong, A ;

Cumming, GR ;

Pike, K .

CHEMICAL COMMUNICATIONS, 2004, (07) :812-813

[6] 3-Acetoxyaminoquinazolinones (QNHOAc) as aziridinating agents: ring-opening of N-(Q)-substituted aziridines [J].

Atkinson, RS .

TETRAHEDRON, 1999, 55 (06) :1519-1558

[7] Catalytic aziridination of olefins and amidation of thioanisole by a non-heme iron complex [J].

Avenier, F ;

Latour, JM .

CHEMICAL COMMUNICATIONS, 2004, (13) :1544-1545

[8] Investigations in the transition metal catalyzed aziridination of olefins, amination, and other insertion reactions with Bromamine-T as the source of nitrene [J].

Chanda, BM ;

Vyas, R ;

Bedekar, AV .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (01) :30-34

[9] Stereocontrolled synthesis of the fully elaborated aziridine core of the azinomycins [J].

Coleman, RS ;

Kong, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (14) :3538-3539

[10] Catalytic aziridination of styrene with copper complexes of substituted 3,7-diazabicyclo[3.3.1]nonanones [J].

Comba, P ;

Merz, M ;

Pritzkow, H .

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2003, (09) :1711-1718

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