Microwave irradiation as a high-speed tool for activation of sluggish aryl chlorides in Grignard reactions

被引：20

作者：

Gold, H ^{[1
]}

Larhed, M ^{[1
]}

Nilsson, P ^{[1
]}

机构：

[1] Uppsala Univ, Dept Med Chem, S-75123 Uppsala, Sweden

来源：

SYNLETT | 2005年 / 10期

关键词：

Grignard reactions; arylations; cross-coupling; microwave; inhibitors;

D O I：

10.1055/s-2005-869856

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Grignard reagents have been generated from reluctant aryl chlorides and bromides using controlled microwave heating to establish a safe, productive and reproducible method. In the synthesis of a novel HIV-1 protease inhibitor, microwave irradiation was both used to generate the starting arylmagnesium halide and to promote a subsequent Kumada coupling.

引用

收藏

页码：1596 / 1600

页数：5

相关论文

共 32 条

[1] Cyclic sulfamide HIV-1 protease inhibitors, with sidechains spanning from P2/P2′ to P1/P1′ [J].

Ax, A ;

Schaal, W ;

Vrang, L ;

Samuelsson, B ;

Hallberg, A ;

Karlén, A .

BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (03) :755-764

[2] MECHANICAL ACTIVATION OF MAGNESIUM TURNINGS FOR THE PREPARATION OF REACTIVE GRIGNARD-REAGENTS [J].

BAKER, KV ;

BROWN, JM ;

HUGHES, N ;

SKARNULIS, AJ ;

SEXTON, A .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :698-703

[3] Chromium(II)-mediated reactions of iodonium tetrafluoroborates with aldehydes: Umpolung of reactivity of diaryl-, alkenyl(aryl)-, and alkynyl(aryl)iodonium tetrafluoroborates [J].

Chen, DW ;

Ochiai, M .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (18) :6804-6814

[4] Transition metal catalyzed cross-coupling of aryl Grignard reagents with aryl fluorides via Pd- or Ni-activation of the C-F bond: an efficient synthesis of unsymmetrical biaryls - application of microwave technology in ligand and catalyst screening [J].

Dankwardt, JW .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (04) :932-938

[5] Nickel-catalyzed cross-coupling of aryl Grignard reagents with aromatic alkyl ethers: An efficient synthesis of unsymmetrical biaryls [J].

Dankwardt, JW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (18) :2428-2432

[6]

Ersmark K, 2004, CURR OPIN DRUG DISC, V7, P417

[7] 2-piperidino-1,1,2-triphenylethanol:: A highly effective catalyst for the enantioselective arylation of aldehydes [J].

Fontes, M ;

Verdaguer, X ;

Solà, L ;

Pericàs, MA ;

Riera, A .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (07) :2532-2543

[8] The preparation of phenylmagnesium chloride in the absence of a solvent [J].

Gilman, H ;

Brown, RE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1930, 52 :3330-3332

[9] THE EFFECTS OF ALKYL SUBSTITUTION IN DRUGS .1. SUBSTITUTED DIMETHYLAMINOETHYL BENZHYDRYL ETHERS [J].

HARMS, AF ;

NAUTA, WT .

JOURNAL OF MEDICINAL & PHARMACEUTICAL CHEMISTRY, 1960, 2 (01) :57-77

[10] Controlled microwave heating in modern organic synthesis [J].

Kappe, CO .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (46) :6250-6284

← 1 2 3 4 →