Synthesis and use of α-aminophosphine oxides and N,N-bis(hosphinoylmethyl)amines - A study on the related ring platinum complexes

被引：38

作者：

Balint, Erika ^{[1
]}

Tripolszky, Anna ^{[2
]}

Jablonkai, Erzsebet ^{[2
]}

Karaghiosoff, Konstantin ^{[3
]}

Czugler, Matyas ^{[1
]}

Mucsi, Zoltan ^{[2
]}

Kollar, Laszlo ^{[4
,5
,6
]}

Pongracz, Peter ^{[4
,5
,6
]}

Keglevich, Gyoergy ^{[2
]}

机构：

[1] MTA BME Res Grp Organ Chem Technol, H-1521 Budapest, Hungary

[2] Budapest Univ Technol & Econ, Dept Organ Chem & Technol, H-1521 Budapest, Hungary

[3] Univ Munich, Dept Chem, D-81377 Munich, Germany

[4] Univ Pecs, Dept Inorgan Chem, H-7624 Pecs, Hungary

[5] Szentagothai Res Ctr, H-7624 Pecs, Hungary

[6] MTA PTE Res Grp Select Chem Synth, H-7624 Pecs, Hungary

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2016年 / 801卷

基金：

匈牙利科学研究基金会;

关键词：

Kabachnik-Fields reaction; alpha-aminophosphine oxides; N; N-bis(phosphinoylmethyl)amines; Bidentate P-ligand; Ring platinum complex; Hydroformylation; KABACHNIK-FIELDS REACTION; FUNCTIONALIZED DITERTIARY PHOSPHINES; MICROWAVE-ASSISTED SYNTHESIS; EFFECTIVE CORE POTENTIALS; ONE-POT SYNTHESIS; AMINO PHOSPHONATES; MOLECULAR CALCULATIONS; SOLVENT-FREE; PHOSPHORUS; CONDENSATION;

D O I：

10.1016/j.jorganchem.2015.10.029

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The Kabachnik-Fields condensation was extended using secondary phosphine oxides, such as dibenzylphosphine oxide and bis(4-methylphenyl) phosphine oxide as the P-reactant in reaction with formaldehyde and different primary amines. Besides the alpha-aminophosphine oxides, the corresponding bisproducts, N,N-bis(phosphinoylmethyl)amines were also synthesized under appropriate conditions. The bis(phosphinoyl)amines were then converted to ring platinum complexes after double deoxygenation. The substituent dependence of the energetics of the complexation reaction using bidentate P-ligands, and the stereostructure of a few complexes were evaluated by B3LYP/6-31G(d,p) calculations using the effective core potential (ECP) basis set (SDD). The crystal structure of a few ring Pt species was studied by X-ray analysis. Catalytic activity of the complexes synthesized was investigated in hydroformylation. (C) 2015 Published by Elsevier B.V.

引用

页码：111 / 121

页数：11

共 62 条

[1] ASYMMETRIC HYDROFORMYLATION [J].

AGBOSSOU, F ;

CARPENTIER, JF ;

MORTREAUX, A .

CHEMICAL REVIEWS, 1995, 95 (07) :2485-2506

[2] Synthesis of N,N-Bis(dialkoxyphosphinoylmethyl)- and N,N-Bis(diphenylphosphinoylmethyl)-β- and γ-amino acid Derivatives by the Microwave-Assisted Double Kabachnik-Fields Reaction [J].

Balint, Erika ;

Fazekas, Eszter ;

Koti, Janos ;

Keglevich, Gyoergy .

HETEROATOM CHEMISTRY, 2015, 26 (01) :106-115

[3] The Synthesis of N,N-Bis(dialkoxyphosphinoylmethyl)- and N,N-Bis(diphenylphosphinoylmethyl) glycine Esters by the Microwave-Assisted Double Kabachnik-Fields Reaction [J].

Balint, Erika ;

Fazekas, Eszter ;

Drahos, Laszlo ;

Keglevich, Gyoergy .

HETEROATOM CHEMISTRY, 2013, 24 (06) :510-515

[4] N-Benzyl and N-aryl bis(phospha-Mannich adducts): Synthesis and catalytic activity of the related bidentate chelate platinum complexes in hydroformylation [J].

Balint, Erika ;

Fazekas, Eszter ;

Pongracz, Peter ;

Kollar, Laszlo ;

Drahos, Laszlo ;

Holczbauer, Tamas ;

Czugler, Matyas ;

Keglevich, Gyoergy .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2012, 717 :75-82

[5] Synthesis and Utilization of the Bis(>P(O)CH2)amine Derivatives Obtained by the Double Kabachnik-Fields Reaction with Cyclohexylamine; Quantum Chemical and X-Ray Study of the Related Bidentate Chelate Platinum Complexes [J].

Balint, Erika ;

Fazekas, Eszter ;

Pinter, Gyoergy ;

Szoellosy, Aron ;

Holczbauer, Tamas ;

Czugler, Matyas ;

Drahos, Laszlo ;

Koertvelyesi, Tamas ;

Keglevich, Gyoergy .

CURRENT ORGANIC CHEMISTRY, 2012, 16 (04) :547-554

[6] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652

[7]

Berners-Price S.J., 1988, STRUCT BONDING, V70, P27, DOI [10.1007/3-540-50130-42, DOI 10.1007/3-540-50130-42]

[8]

Botteghi C., 1998, Transition Metals for Organic Synthesis, P25

[9]

Brunner H., 1993, HDB ENANTIOSELECTIVE

[10]

Cherkasov R A., 2009, Russ. J. Gen. Chem, V79, P1480

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