Palladium coupling catalysts for pharmaceutical applications

Current Opinion in Drug Discovery and Development

Volumn 10, Issue 6, 2007, Pages 672-690

  Doucet, H ^a   Hierso, J C ^b  

^a UNIVERSITÉ DE RENNES 1   (France)

^b UNIVERSITÉ DE BOURGOGNE   (France)

Author keywords

C H activation; Catalysis; Cross coupling; Palladium

Indexed keywords

1,1' BIS(DIPHENYLPHOSPHINO)FERROCENE; ANTICOAGULANT AGENT; BENZENE DERIVATIVE; HYDRAZINE DERIVATIVE; INDOLE DERIVATIVE; INDOLIZINE DERIVATIVE; N,N DIALKYL 1 N' ARYLHYDRAZINE; PALLADIUM; PHOSPHINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARYLATION; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIELS ALDER REACTION; DRUG INDUSTRY; DRUG MANUFACTURE; ETHERIFICATION; HYDROLYSIS; ISOMERISM; METHYLATION; REVIEW; SUZUKI REACTION;

CATALYSIS; DRUG DESIGN; DRUG INDUSTRY; MOLECULAR STRUCTURE; PALLADIUM; PHARMACEUTICAL PREPARATIONS;

EID: 35948956310     PISSN: 13676733     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (39)

1. Tsuji J (Ed): Topics in Organometallic Chemistry. Palladium in Organic Synthesis. Springer-Verlag, Berlin, Germany (2005) 14.
2. Tsuji J (Ed): Palladium Reagents and Catalysis: New Perspectives for the 21st Century. John Wiley & Sons Ltd, Chichester, UK (2004).
3. Alberico D, Scott ME, Lautens M: Aryl-aryl bond formation by transition-metal-catalyzed direct arylation. Chem Rev (2007) 107(1):174-238.
4. Fernández-Rodríguez MA, Shen Q, Hartwig JF: Highly efficient and functional-group-tolerant catalysts for palladium-catalyzed coupling of aryl chlorides with thiols. Chem Eur J (2006) 12(30):7782-7796. • Describes an efficient procedure for the coupling of thiols with aryl chlorides employing a ferrocenyl diphosphine ligand.
5. Cacchi S, Fabrizi G, Goggiamani A, Sgalla S: Palladium-catalyzed N-arylation of N,N-dialkylhydrazines with aryl chlorides. Adv Synth Catal (2007) 349(3):453-458.
6. 6]. Tetrahedron Lett (2007) 48(7):1087-1090.
7. Liégault B, Renaud J-L, Bruneau C: Palladium-catalyzed synthesis of functional tetralins via benzylic activation. Adv Synth Catal (2007) 349(6):841-845.
8. Sebelius S, Olsson VJ, Wallner OA, Szabó KJ: Palladium- catalyzed coupling of allylboronic acids with iodobenzenes. Selective formation of the branched allylic product in the absence of directing groups. J Am Chem Soc (2006) 128(25):8150-8151.
9. Liu Y, Song Z, Yan B: General and direct synthesis of 3-aminoindolizines and their analogues via Pd/Cu-catalyzed sequential cross-coupling/cycloisomerization reaction. Org Lett (2007) 9(3):409-412.
10. Shen Q, Hartwig JF: Palladium-catalyzed coupling of ammonia and lithium amide with aryl halides. J Am Chem Soc (2006) 128(31):10028-10029. • Describes a simple procedure for the preparation of anilines in the presence of a ferrocenyl diphosphine ligand.
11. 2(dppf).
12. Molander GA, Vargas F: β-Aminoethyltrifluoroborates: Efficient aminoethylations via Suzuki-Miyaura cross-coupling. Org Lett (2007) 9(2):203-206.
13. Barluenga J, Valdés C, Beltrán G, Escribano M, Aznar F: Developments in Pd catalysis: Synthesis of 1H-1,2,3-triazoles from sodium azide and alkenyl bromides. Angew Chem Int Ed (2006) 45(41):6893-6896. •• Describes a powerful and direct synthesis of triazoles from simple sodium azide and alkenyl bromides using a large bite angle non-electron-rich diphosphine ligand.
14. Takemiya A, Hartwig JF: Palladium-catalyzed synthesis of aryl ketones by coupling of aryl bromides with an acyl anion equivalent. J Am Chem Soc (2006) 128(46):14800-14801.
15. Neumann H, Brennführer A, Groß P, Riermeier T, Almena J, Beller M: Efficient carbonylation of aryl and heteroaryl bromides using a palladium/diadamantylbutylphosphine catalyst. Adv Synth Catal (2006) 348(10-11):1255-1261.
16. Guram AS, King AO, Allen JG, Wang X, Schenkel LB, Chan J, Bunel EE, Faul MM, Larsen RD, Martinelli MJ, Reider PJ: New air-stable catalysts for general and efficient Suzuki-Miyaura cross-coupling reactions of heteroaryl chlorides. Org Lett (2006) 8(9):1787-1789.
17. 3.
18. Billingsley KL, Anderson KW, Buchwald SL: A highly active catalyst for the Suzuki-Miyaura cross-coupling reactions of heteroaryl compounds. Angew Chem Int Ed (2006) 45(21):3484-3488.
19. Anderson KW, Tundel RE, Ikawa T, Altman RA, Buchwald SL: Monodentate phosphines provide highly active catalysts for Pd-catalyzed C-N bond-forming reactions of heteroaromatic halides/amines and (H)N-heterocycles. Angew Chem Int Ed (2006) 45(39):6523-6527. • Describes an efficient procedure for the amination of aryl halides with (biaryl)dialkylphosphine ligands.
20. Burgos CH, Barder TE, Huang X, Buchwald SL: Significantly improved method for the Pd-catalyzed coupling of phenols with aryl halides: Understanding ligand effects. Angew Chem Int Ed (2006) 45(26):4321-4326.
21. Anderson KW, Ikawa T, Tundel RE, Buchwald SL: The selective reaction of aryl halides with KOH: Synthesis of phenol, aromatic ethers and benzofurans. J Am Chem Soc (2006) 128(33):10694-10695. • Describes a novel palladium-catalyzed preparation of neutral or electron-rich 2-substituted phenols directly from aryl and heteroaryl bromides and chlorides employing a (biaryl)dialkylphosphine ligand and potassium hydroxide.
22. Billingsley K, Buchwald SL: Highly efficient monophosphine-based catalyst for the palladium-catalyzed Suzuki-Miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters. J Am Chem Soc (2007) 129(11):3358-3366. • Describes the Suzuki-Miyaura coupling of heteroaromatics using (biaryl)dialkylphosphine ligands as catalysts.
23. Chiong A, Daugulis O: Palladium-catalyzed arylation of electron-rich heterocycles with aryl chlorides. Org Lett (2007) 9(8):1449-1451. •• Describes a useful and simple procedure for the direct coupling of heteroaromatics with aryl chlorides employing the electron-rich, sterically hindered ligand diadamantylbutylphosphane.
24. Ackermann L, Althammer A: Domino N-C/C-H bond activation: Palladium-catalyzed synthesis of annulated heterocycles using dichloro(hetero)arenes. Angew Chem Int Ed (2007) 46(10):1627- 1629.
25. Leclerc J-P, Fagnou K: Palladium-catalyzed cross-coupling reaction of diazine N-oxides with aryl chlorides, bromides and iodides. Angew Chem Int Ed (2006) 45(46):7781-7786. •• Describes the direct arylation of diazines with an electron-rich and sterically hindered ligand.
26. Hulcoop DG, Lautens M: Palladium-catalyzed annulation of aryl heterocycles with strained alkenes. Org Lett (2007) 9(9):1761-1764.
27. Ren H, Knochel P: Chemoselective benzylic C-H activation for the preparation of condensed N-heterocycles. Angew Chem Int Ed (2006) 45(21):3462-3465.
28. Deprez NR, Kalyani D, Krause A, Sanford MS: Room temperature palladium-catalyzed 2-arylation of indoles. J Am Chem Soc (2006) 128(15):4972-4973.
29. Wang X, Gribkov DV, Sames D: Phosphine-free palladium-catalyzed C-H bond arylation of free (N-H)-indoles and pyrroles. J Org Chem (2007) 72(4):1476-1479.
30. Zhang Z, Hu Z, Yu Z, Lei P, Chi H, Wang Y, He R: Direct palladium-catalyzed C-3 arylation of indoles. Tetrahedron Lett (2007) 48(13):2415-2419.
31. Ma S, Yu S, Peng Z, Guo H: Palladium-catalyzed functionalization of indoles with 2-acetoxymethyl-substituted electron-deficient alkenes. J Org Chem (2006) 71(26):9865-9868. • Describes an extension of the C-H activation reaction with allyl acetates using a bipyridine as the ligand, which gives ready access to functionalized indoles.
32. Seregin IV, Ryabova V, Gevorgyan V: Direct palladium-catalyzed alkynylation of N-fused heterocycles. J Am Chem Soc (2007) 129(25):7742-7743.
33. Chuprakov S, Chernyak N, Dudnik AS, Gevorgyan V: Direct Pd-catalyzed arylation of 1,2,3-triazoles. Org Lett (2007) 9(12):2333-2336.
34. Desai LV, Malik HA, Sanford MS: Oxone as an inexpensive, safe and environmentally benign oxidant for C-H bond oxygenation. Org Lett (2006) 8(6):1141-1144.
35. Shabashov D, Daugulis O: Ortho-arylation of benzamides. Org Lett (2006) 8(21):4947-4949.
36. Chiong HA, Pham Q-N, Daugulis O: Two methods for direct orthoarylation of benzoic acids. J Am Chem Soc (2007) 129(32):9879-9884.
37. Zhou C, Larock RC: Synthesis of aryl ketones or ketimines by palladium-catalyzed arene C-H addition to nitriles. J Org Chem (2006) 71(9):3551-3558.
38. 3 C-H bonds with methylboroxine and alkylboronic acids: Two distinct C-H activation pathways. J Am Chem Soc (2006) 128(39):12634-12635.
39. 3 C-H bonds in simple carboxylic acids. J Am Chem Soc (2007) 129(12):3510-3511.