Applications of phosphine-functionalised polymers in organic synthesis.

This tutorial review deals with recent advances in the use of phosphine-functionalised polymers in organic synthesis. In the first part of the review, some recent applications of polymer-supported palladium catalysts are reviewed, particularly recyclable catalysts for C-C and C-X bond formation with aryl bromide and chloride substrates. In the second half, novel applications of phosphine-functionalised polymers as reagents, scavengers, organocatalysts and linkers in organic chemistry are presented. Emphasis is placed on the synthesis of biologically active molecules.

[1]  Christopher W. Jones,et al.  On the Nature of the Active Species in Palladium Catalyzed Mizoroki–Heck and Suzuki–Miyaura Couplings – Homogeneous or Heterogeneous Catalysis, A Critical Review , 2006 .

[2]  M. Sugiura,et al.  Practical preparation method of polymer-incarcerated (PI) palladium catalysts using Pd(II) salts. , 2006, Organic letters.

[3]  D. Sauer,et al.  A simple and efficient one step synthesis of 1,3,4-oxadiazoles utilizing polymer-supported reagents and microwave heating , 2006 .

[4]  D. Spring,et al.  Synthesis and utilization of functionalized polystyrene resins , 2005 .

[5]  M. Shi,et al.  Optimization of polystyrene-supported triphenylphosphine catalysts for Aza-morita-baylis-hillman reactions , 2005 .

[6]  L. Hennequin,et al.  Selective alkylation of a 6,7-dihydroxyquinazoline , 2005 .

[7]  S. Ghosh,et al.  Synthesis of 3-amino-1,2,4-benzothiadi- azine 1,1-dioxides via a tandem aza-Wittig/heterocumulene annulation. , 2005, The Journal of organic chemistry.

[8]  K. K. Hii,et al.  Recyclable Polymer‐Supported Pd Catalysts for Aryl Amination Reactions. , 2005 .

[9]  K. K. Hii,et al.  Phosphine-functionalised polymer resins as Pd scavengers , 2005 .

[10]  Chao‐Jun Li,et al.  Efficient Trost's γ-addition catalyzed by reusable polymer-supported triphenylphosphine in aqueous media , 2005 .

[11]  Huanfeng Jiang,et al.  Polymeric tertiaryphosphine as a green and recyclable organocatalyst for stereoselective isomerization reaction , 2005 .

[12]  V. Ananikov,et al.  The First Example of Polymer-Supported Palladium Catalyst for Stereo­selective S-S Bond Addition to Terminal Alkynes , 2005 .

[13]  R. Schobert,et al.  An expedient synthesis of 3-acyltetramic acids of the melophlin family from α-aminoesters and immobilized Ph3PCCO , 2005 .

[14]  D. Sauer,et al.  Rapid and efficient synthesis of 1,2,4-oxadiazoles utilizing polymer-supported reagents under microwave heating. , 2005, Organic letters.

[15]  U. Scholz,et al.  Palladium‐Catalyzed CN and CO Coupling–A Practical Guide from an Industrial Vantage Point† , 2004 .

[16]  G. Mullen,et al.  Synthesis and reactions of polymer-bound Ph3P=C=C=O: a quick route to tenuazonic acid and other optically pure 5-substituted tetramates. , 2004, Organic & biomolecular chemistry.

[17]  R. Srivastava,et al.  Application of polymer-supported triphenyl phosphine in the palladium-catalyzed cyanation reaction under microwave conditions , 2004 .

[18]  A. Kirschning,et al.  Polymer‐Bound Diphenylphosphane Hydrobromide, a Mild Acid for the Activation of Enol Ethers: Applications in Polymer‐Assisted Glycosidations , 2004 .

[19]  D. Sauer,et al.  Use of polymer-supported Pd reagents for rapid and efficient Suzuki reactions using microwave heating. , 2004, Organic letters.

[20]  W. A. Loughlin,et al.  Novel polymer-supported coupling/dehydrating reagents for use in organic synthesis. , 2004, Organic & biomolecular chemistry.

[21]  R. Breinbauer,et al.  An efficient and inexpensive scavenger resin for Grubbs' catalyst , 2004 .

[22]  M. Sugiura,et al.  Phosphine oxides as efficient neutral coordinate-organocatalysts for stereoselective allylation of N-acylhydrazones. , 2004, Organic & biomolecular chemistry.

[23]  Jonathan D. Wilden,et al.  Direct synthesis of sulfonamides and activated sulfonate esters from sulfonic acids. , 2004, Journal of the American Chemical Society.

[24]  K. Schöning,et al.  Immobilized catalysts in industrial research and application. , 2004, Topics in current chemistry.

[25]  Y. Uozumi.  Recent progress in polymeric palladium catalysts for organic synthesis. , 2004, Topics in current chemistry.

[26]  J. Berger,et al.  Application of an almost traceless linker in the synthesis of 2-alkylthiobenzimidazole combinatorial libraries , 2004, Molecular Diversity.

[27]  P. Toy,et al.  Direct radical polymerization of 4-styryldiphenylphosphine: preparation of cross-linked and non-cross-linked triphenylphosphine-containing polystyrene polymers. , 2003, The Journal of organic chemistry.

[28]  M. Maier,et al.  A formal total synthesis of the salicylihalamides. , 2003, The Journal of organic chemistry.

[29]  B. Snider,et al.  Synthesis of (+/-)-phloeodictine A1. , 2003, Organic letters.

[30]  Chia-Fu Lee,et al.  Acetonyltriphenylphosphonium Bromide and Its Polymer-Supported Analogues as Catalysts for the Protection of Carbonyl Compounds as Acetals or Thioacetals , 2003 .

[31]  N. Leadbeater.  Polymer-supported metal-phosphine complexes for use as catalysts or linkers in medicinally-oriented organic synthesis. , 2002, Current medicinal chemistry.

[32]  E. Pedroso,et al.  Synthesis of amino- and guanidino-G-clamp PNA monomers. , 2002, Organic letters.

[33]  N. Leadbeater,et al.  Preparation of polymer-supported ligands and metal complexes for use in catalysis. , 2002, Chemical reviews.

[34]  M. Lizarzaburu,et al.  Synthesis of aryl ethers from aminoalcohols using polymer-supported triphenylphosphine , 2002 .

[35]  J. Westman.  An efficient combination of microwave dielectric heating and the use of solid-supported triphenylphosphine for Wittig reactions. , 2001, Organic letters.

[36]  Ping-hui Szu,et al.  Acetonyltriphenylphosphonium bromide and its polymer-supported analogues as catalysts in protection and deprotection of alcohols as alkyl vinyl ethers , 2001 .

[37]  S. Buchwald,et al.  Use of polymer-supported dialkylphosphinobiphenyl ligands for palladium-catalyzed amination and Suzuki reactions. , 2001, Journal of Organic Chemistry.

[38]  J. Mayer,et al.  A polymer-bound iminophosphorane approach for the synthesis of quinazolines. , 2001, Journal of combinatorial chemistry.

[39]  N. Miyaura,et al.  The Cross-Coupling Reaction of Arylboronic Acids with Chloropyridines and Electron-Deficient Chloroarenes Catalyzed by a Polymer-Bound Palladium Complex , 2000 .

[40]  R. Grigg,et al.  Bimetallic catalytic cascade ring closing metathesis—intramolecular Heck reactions using a fluorous biphasic solvent system or a polymer-supported palladium catalyst , 2000 .

[41]  G. Georg,et al.  The use of polymer-bound triphenylphosphine in the stereochemical inversion of secondary alcohols. , 2000, Combinatorial chemistry & high throughput screening.

[42]  D. Drewry,et al.  Solid‐supported reagents in organic synthesis , 1999, Medicinal research reviews.

[43]  G. Georg,et al.  Polymer-bound triphenylphosphine as traceless reagent for mitsunobu reactions in combinatorial chemistry: Synthesis of aryl ethers from phenols and alcohols , 1998 .

[44]  I. Hughes.  Design of self-coded combinatorial libraries to facilitate direct analysis of ligands by mass spectrometry. , 1998, Journal of medicinal chemistry.

[45]  C. L. Drian,et al.  Reusable polymer-supported palladium catalysts: An alternative to tetrakis(triphenylphosphine)palladium in the Suzuki cross-coupling reaction , 1998 .

[46]  P. Stanetty,et al.  SYNTHESIS OF (E)-NITRO OLEFINS BY ISOMERISATION OF (Z)-NITRO OLEFINS WITH POLYMER-SUPPORTED TRIPHENYLPHOSPHINE , 1998 .

[47]  S. Jang.  Polymer-bound palladium-catalyzed cross-coupling of organoboron compounds with organic halides and organic triflates , 1997 .

[48]  S. Alexandratos,et al.  Microenvironmental effect in polymer-supported reagents. 1. Influence of copolymer architecture on the Mitsunobu reaction , 1996 .

[49]  I. Hughes.  Application of polymer-bound phosphonium salts as traceless supports for solid phase synthesis , 1996 .

[50]  D. Cech,et al.  A facile solid phase synthesis of 2′- and 3′-aminonucleoside triphosphates , 1996 .

[51]  C. Andersson,et al.  Palladium/phosphinated polystyrene as a catalyst in the Heck arylation. A comparative study , 1985 .

[52]  T. Imanaka,et al.  A coordinatively unsaturated, polymer-bound palladium(0) complex. Synthesis and catalytic activities , 1978 .

[53]  J. Fréchet,et al.  Bromination and lithiation: two important steps in the functionalization of polystyrene resins , 1976 .