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

被引:50
作者
Balint, Erika [1 ]
Fazekas, Eszter [1 ]
Pongracz, Peter [2 ,3 ]
Kollar, Laszlo [2 ,3 ]
Drahos, Laszlo [4 ]
Holczbauer, Tamas [4 ]
Czugler, Matyas [4 ]
Keglevich, Gyoergy [1 ]
机构
[1] Budapest Univ Technol & Econ, Dept Organ Chem & Technol, H-1521 Budapest, Hungary
[2] Univ Pecs, Dept Inorgan Chem, H-7624 Pecs, Hungary
[3] Szentagothai Res Ctr, H-7624 Pecs, Hungary
[4] Hungarian Acad Sci, Res Ctr Nat Sci, Inst Organ Chem, Dept Struct Chem, H-1525 Budapest, Hungary
关键词
Kabachnik-Fields reaction; N; N-Bis(> P(O)-methyl)amine derivatives; Bidentate chelate platinum complex; Hydroformylation; KABACHNIK-FIELDS REACTION; MICROWAVE-ASSISTED SYNTHESIS; ALPHA-AMINO PHOSPHONATES; DIETHYL PHOSPHITE; P-HETEROCYCLES; SOLVENT-FREE; AMINOPHOSPHONATES; CYCLOHEXYLAMINE; BENZALDEHYDE; DERIVATIVES;
D O I
10.1016/j.jorganchem.2012.07.031
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The microwave-assisted double Kabachnik-Fields (phospha-Mannich) reaction of benzylamine and arylamines, two equivalents of paraformaldehyde and the > P(O)H reagent, such as dialkyl phosphites, ethyl phenyl-H-phosphinate and diphenylphosphine oxide gave the bis(> P(O)CH2) amine derivatives in good yields. The bis(diphenylphosphinoxido) derivatives were converted to the corresponding ring platinum complexes after deoxygenation whose catalytic activity was tested in the hydroformylation of styrene. Crystal structure analysis of one of the complexes reveals interesting correlations between complex structure and solvent inclusion. (C) 2012 Elsevier B. V. All rights reserved.
引用
收藏
页码:75 / 82
页数:8
相关论文
共 32 条
[1]   The Cambridge Structural Database: a quarter of a million crystal structures and rising [J].
Allen, FH .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 2002, 58 (3 PART 1) :380-388
[2]   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
[3]   Hydrogen bonding in organometallic crystals .6. X-H---M hydrogen bonds and M---(H-X) pseudo-agostic bonds [J].
Braga, D ;
Grepioni, F ;
Tedesco, E ;
Biradha, K ;
Desiraju, GR .
ORGANOMETALLICS, 1997, 16 (09) :1846-1856
[4]   Agostic interactions in transition metal compounds [J].
Brookhart, Maurice ;
Green, Malcolm L. H. ;
Parkin, Gerard .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2007, 104 (17) :6908-6914
[5]   Reversal of enantioselectivity in the hydroformylation of styrene with [2S,4S-BDPP]Pt(SnCl3)Cl at high temperature arises from a change in the enantioselective-determining step [J].
Casey, CP ;
Martins, SC ;
Fagan, MA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (17) :5585-5592
[6]  
Cherkasov R A., 2009, Russ. J. Gen. Chem, V79, P1480
[7]  
CHERKASOV RA, 1998, RUSS CHEM REV, V67, P857, DOI [DOI 10.1070/RC1998V067N10ABEH000421, 10.1070/RC1998v067n10ABEH000421]
[8]   THE SYNTHESIS OF ESTERS OF SUBSTITUTED AMINO PHOSPHONIC ACIDS [J].
FIELDS, EK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (06) :1528-1531
[9]   Synthesis of natural products containing a C-P bond [J].
Fields, SC .
TETRAHEDRON, 1999, 55 (42) :12237-12272
[10]   The most potent organophosphorus inhibitors of leucine aminopeptidase. Structure-based design, chemistry, and activity [J].
Grembecka, J ;
Mucha, A ;
Cierpicki, T ;
Kafarski, P .
JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (13) :2641-2655