Novel Phosphinite and Phosphonite Copper(I) Complexes: Efficient Catalysts for Click Azide-Alkyne Cycloaddition Reactions

被引：51

作者：

Lal, Steven ^{[1
]}

McNally, Jayne ^{[1
]}

White, Andrew J. P. ^{[1
]}

Diez-Gonzalez, Silvia ^{[1
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

来源：

ORGANOMETALLICS | 2011年 / 30卷 / 22期

基金：

英国工程与自然科学研究理事会;

关键词：

M4X4; CORE; MOLECULAR-STRUCTURE; CONJUGATE ADDITION; LIGANDS; CHEMISTRY; DIETHYLZINC; SILVER(I); CRYSTAL;

D O I：

10.1021/om200791u

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The preparation of novel phosphinite- and phosphonite-bearing copper(I) complexes of the general formula [CuX(L)] is reported. These compounds, which remain scarce in the literature, could be prepared using readily available starting materials and were spectroscopically and structurally characterized. These complexes, together with their known phosphine and phosphite analogues, were then applied to the 1,3-dipolar cycloaddition of azides and alkynes, to find that the new complexes displayed the best activities. Full optimization of the reaction conditions resulted in a noteworthy Click catalytic system, active under very mild reaction conditions in the absence of any additive and using low metal loadings.

引用

页码：6225 / 6232

页数：8

共 51 条

[11] MOLECULES WITH AN M4X4 CORE .2. X-RAY CRYSTALLOGRAPHIC DETERMINATION OF MOLECULAR-STRUCTURE OF TETRAMERIC TRIPHENYLPHOSPHINECOPPER(I) BROMIDE IN CRYSTALLINE [PPH3CUBR]4.2CHCL3 [J].

CHURCHILL, MR ;

KALRA, KL .

INORGANIC CHEMISTRY, 1974, 13 (06) :1427-1434

[12] MOLECULES WITH AN M4X4 CORE .1. CRYSTAL AND MOLECULAR-STRUCTURE OF TETRAMERIC TRIPHENYLPHOSPHINECOPPER(I) CHLORIDE, A CUBANE-LIKE MOLECULE, INCLUDING LOCATION AND REFINEMENT OF ALL HYDROGEN-ATOMS [J].

CHURCHILL, MR ;

KALRA, KL .

INORGANIC CHEMISTRY, 1974, 13 (05) :1065-1071

[13] MOLECULES WITH AN M4X4 CORE .4. CRYSTALLOGRAPHIC DETECTION OF A STEP CONFIGURATION FOR CU4I4 CORE IN TETRAMERIC TRIPHENYLPHOSPHINECOPPER(I) IODIDE, [PPH3CUI]4 [J].

CHURCHILL, MR ;

DEBOER, BG ;

DONOVAN, DJ .

INORGANIC CHEMISTRY, 1975, 14 (03) :617-623

[14] ORGANO-PHOSPHORUS COMPOUNDS .18. SYNTHESIS OF 2-PHENYL-2,3-DIHYDRO-1H-1,2-BENZAZAPHOSPHOLE 2-SULFIDE BY PYROLYSIS OF (2-AMINOBENZYL)PHENYLDITHIOPHOSPHINIC ACID [J].

COLLINS, DJ ;

DRYGALA, PF ;

SWAN, JM .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1983, 36 (10) :2095-2110

[15] TRANSITION-METAL COMPLEXES CONTAINING PHOSPHORUS LIGANDS .12. CATIONIC DIALKYL PHENYLPHOSPHONITE AND ALKYL DIPHENYLPHOSPHINITE DERIVATIVES OF COPPER, SILVER, GOLD AND PLATINUM METALS [J].

COUCH, DA ;

ROBINSON, SD .

INORGANIC CHEMISTRY, 1974, 13 (02) :456-462

[16] Well-defined copper(I) complexes for Click azide-alkyne cycloaddition reactions: one Click beyond [J].

Diez-Gonzalez, Silvia .

CATALYSIS SCIENCE & TECHNOLOGY, 2011, 1 (02) :166-178

[17] [(NHC)CuX] complexes: Synthesis, characterization and catalytic activities in reduction reactions and Click Chemistry. On the advantage of using well-defined catalytic systems [J].

Diez-Gonzalez, Silvia ;

Escudero-Adan, Eduardo C. ;

Benet-Buchholz, Jordi ;

Stevens, Edwin D. ;

Slawin, Alexandra M. Z. ;

Nolan, Steven P. .

DALTON TRANSACTIONS, 2010, 39 (32) :7595-7606

[18] SOLUTION EQUILIBRIA OF TERTIARY PHOSPHINE COMPLEXES OF COPPER(I) HALIDES [J].

FIFE, DJ ;

MOORE, WM ;

MORSE, KW .

INORGANIC CHEMISTRY, 1984, 23 (12) :1684-1691

[19] Highly active copper-catalysts for azide-alkyne cycloaddition [J].

Gonda, Zsombor ;

Novak, Zoltan .

DALTON TRANSACTIONS, 2010, 39 (03) :726-729

[20] Branched-regioselective hydroformylation with catalytic amounts of a reversibly bound directing group [J].

Gruenanger, Christian U. ;

Breit, Bernhard .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (38) :7346-7349

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