Synthesis of Water-Soluble Phosphine Oxides by Pd/C-Catalyzed P-C Coupling in Water

被引:79
作者
Rummelt, Stephan M. [1 ,2 ]
Ranocchiari, Marco [1 ]
van Bokhoven, Jeroen A. [1 ,2 ]
机构
[1] Paul Scherrer Inst, Dept Synchrotron Radiat & Nanotechnol, CH-5232 Villigen, Switzerland
[2] ETH, Dept Chem & Appl Biosci, CH-8093 Zurich, Switzerland
关键词
PHOSPHORUS-CARBON BOND; SECONDARY PHOSPHINES; ARYL PHOSPHINES; PALLADIUM; LIGANDS; TRIPHENYLPHOSPHINE; TRIARYLPHOSPHINES; COMPLEXES; HALIDES; THIOLS;
D O I
10.1021/ol300582y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cross-coupling between diphenylphosphine oxide and halogenated benzoic acids catalyzed by Pd/C in water is a green, simple, and fast protocol to obtain water-soluble tertiary phosphine oxides without the addition of ligands and additives. Low reaction times and microwave irradiation make this method general and excellent for laboratory and large-scale synthesis without the need to use organic solvents in reactions and workup.
引用
收藏
页码:2188 / 2190
页数:3
相关论文
共 38 条
[1]   PHOSPHINE VS PHOSPHINE OXIDE LIGANDS IN HYDROFORMYLATION REACTIONS [J].
ABUGNIM, C ;
AMER, I .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (01) :115-117
[2]   Phosphine oxides as ligands in the hydroformylation reaction [J].
AbuGnim, C ;
Amer, I .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1996, 516 (1-2) :235-243
[3]   Catalytic methods for building up phosphorus-carbon bond [J].
Beletskaya, IP ;
Kazankova, MA .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 38 (10) :1391-1430
[4]   Chiral phosphine oxides in present-day organocatalysis [J].
Benaglia, Maurizio ;
Rossi, Sergio .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (17) :3824-3830
[5]   Water soluble phosphines - Part XV. Syntheses of multiply functionalized and chiral phosphine ligands by Pd-catalyzed P-C and C-C coupling reactions [J].
Brauer, DJ ;
Hingst, M ;
Kottsieper, KW ;
Liek, C ;
Nickel, T ;
Tepper, M ;
Stelzer, O ;
Sheldrick, WS .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 645 (1-2) :14-26
[6]   SYNTHESIS OF CHIRAL 2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL (BINAP) VIA A NOVEL NICKEL-CATALYZED PHOSPHINE INSERTION [J].
CAI, DW ;
PAYACK, JF ;
BENDER, DR ;
HUGHES, DL ;
VERHOEVEN, TR ;
REIDER, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (23) :7180-7181
[7]   Remarkable ligand effect on the enantioselectivity of the chiral lanthanum complex-catalyzed asymmetric epoxidation of enones [J].
Daikai, K ;
Kamaura, M ;
Inanaga, J .
TETRAHEDRON LETTERS, 1998, 39 (40) :7321-7322
[8]   Phosphine oxides as stabilizing ligands for the palladium-catalyzed cross-coupling of potassium aryldimethylsilanolates [J].
Denmark, Scott E. ;
Smith, Russell C. ;
Tymonko, Steven A. .
TETRAHEDRON, 2007, 63 (26) :5730-5738
[9]   Structures and catalytic properties of triphenylphosphine oxide complexes of scandium and lanthanide triflates [J].
Fawcett, J ;
Platt, AWG ;
Russell, DR .
POLYHEDRON, 2002, 21 (03) :287-293
[10]   Synthesis, characterization and reactivity of MoCl2(O)(O2)(OPR3)2, OPR3 = OPMePh2,OPPh3; an isomerization catalyst for some allylic alcohols [J].
Fronczek, FR ;
Luck, RL ;
Wang, G .
INORGANIC CHEMISTRY COMMUNICATIONS, 2002, 5 (06) :384-387