Palladium-catalysed coupling reactions

Topics in Organometallic Chemistry

Volumn 42, Issue , 2012, Pages 1-34

  De Vries, Johannes G ^a  

^a DSM RESOLVE   (Netherlands)

Author keywords

Agrochemicals; Carbon carbon bond formation; Cross coupling; Flavours and fragrances; Monomers; Palladium; Pharmaceuticals; Production process

Indexed keywords

EID: 84867056821     PISSN: 14366002     EISSN: None     Source Type: Book Series    
DOI: 10.1007/3418-2012-32     Document Type: Article

References (119)

1. Carey JS, Laffan D, Thomson C, Williams MT (2006) Org Biomol Chem 4:2337-47
2. Magano J, Dunetz JR (2011) Chem Rev 111:2177-250
3. Heck RF (1982) Org React 27:345-90
4. Heck RF (1991) In: Trost BM, Fleming I (eds) Comprehensive organic synthesis, vol 4. Pergamon Press, Oxford, pp 833-63
5. Br€ase S, de Meijere A (1998) In: Diederich F, Stang PJ (eds) Metal-catalyzed cross-coupling reactions. Wiley-VCH, Weinheim, pp 99-166
6. Beletskaya IP, Cheprakov AV (2000) Chem Rev 100:3009-66
7. de Vries JG (2001) Can J Chem 79:1086-92
8. Oestreich M (ed) (2008) The Mizoroki-Heck reaction. Wiley-VCH, Weinheim
9. Reetz MT, de Vries JG (2004) Chem Commun 1559-1563
10. de Vries JG (2006) Dalton Trans 421-429
11. Ritter K (1993) Synthesis 735-762
12. Blaser H-U, Spencer A (1982) J Organomet Chem 233:267-74
13. Miura M, Hashimoto H, Itoh K, Nomura M (1990) J Chem Soc Perkin Trans I 2207-2215
14. Kikukawa K, Matsuda T (1977) Chem Lett 159-162
15. Stephan MS, Teunissen AJJM, Verzijl GKM, de Vries JG (1998) Angew Chem Int Ed Engl :662-4
16. Portnoy M, Ben-David Y, Rousso I, Milstein D (1994) Organometallics 13:3465-79
17. Herrmann WA, Brossmer C, Reisinger C-P, Riermeier TH, O ̈ fele K, Beller M (1997) Chemt Eur J 3:1357-64
18. Beller M, Zapf A (1998) Synlett 7:792-3
19. Reetz MT, Lohmer G, Schwickardi R (1998) Angew Chem Int Ed Engl 37:481-3
20. Littke AP, Fu GC (1999) J Org Chem 64:10-1
21. Hirabayashi K, Nishihara Y, Mori A, Hiyama T (1998) Tetrahedron Lett 39:7893-6
22. Cabri W, Candiani I (1995) Acc Chem Res 28:2-7
23. Baumeister P, Meyer W, Oertle K, Seifert G (1997) In: Siegrist U, Steiner H, Blaser H-U, Baiker A, Prins R (eds) Heterogeneous catalysis and fine chemicals IV. Elsevier Science BV, Amsterdam, pp 37-40
24. Bader RR, Baumeister P, Blaser H-U (1996) Chimia 50:99-105
25. Eisenstadt A (1998) In: Herkes FE (ed) Catalysis of Organic Reactions (Chemical Industries), Vol 75, pp 415-427
26. Pr€ockl SS, Kleist W, Gruber MA, K€ohler K (2004) Angew Chem Int Ed 43:1881-2
27. McChesney J (1999) Spec Chem 6:98
28. Lin RW, Herndon R, Allen RH, Chockalingham KC, Focht GD, Roy RK (1998) WO98/Albemarle Corporation.Baton Rouge
29. Ramachandran V, Wu T-C, Berry CB (1998) WO9837052, Albemarle Corporation, Baton Rouge
30. DeVries RA, Vosejpka PC, Ash ML (1998) In: Herkes FE (ed) Catalysis of Organic Reactions (Chemical Industries), Vol 75
31. Shinkai I, King AO, Larsen RD (1994) Pure Appl Chem 66:1551-6
32. Belley ML, Leger S, Roy P, Xiang YB, Labelle M, Guay D (1992) EP0480717, Merck Frosst Canada Inc., Toronto
33. de Vries AHM, Mulders JMCA, Mommers JHM, Henderickx HJW, de Vries JG (2003) Org Lett 5:3285-8
34. de Vries AHM, Parlevliet FJ, Schmieder-van de Vondervoort L, Mommers JHM, Henderickx. HJW, Walet MAN, de Vries JG (2002) Adv Synth Catal 344:996-1002
35. Lifshitz-Liron R (2007) WO2007/127449, Teva Pharmaceutical Industries Ltd., Petah Tikya
36. Lifshitz-Liron R, Eisenstadt A, Wizel S, Avhar-Maydan S, Raizi Y, Ramati R (2006) WO2006/125026, Teva Pharmaceutical Industries Ltd.,Petah Tikya
37. Macor JE, Wythes MJ (1992) WO1992/006973, Pfizer Inc., New York
38. Ashcroft CP, Hellier P, Pettman A, Watkinson S (2011) Org Proc Res Dev 15:98-103
39. Ogilvie RJ (2002) WO2002/050063, Pfizer Ltd, Mumbai
40. Volpicelli R, Maragni P, Cotarca L, Foletto J, Massaccesi F (2008) WO2008/064827, Zach System S.P.A., Lonigo Vicenza
41. Taylor EC, Kuhnt D, Shih C, Rinzel SM, Grindey GB, Barredo J, Jannatipour M, Moran RG J Med Chem 35:4450-4
42. Kjell DP, Hallberg DW, Kalbfleisch JM, McCurry CK, Semo MJ, Sheldon EM, Spitler JT, Wang M (2005) Org Proc Res Dev 9:738-42
43. Kjell DP, Slattery BJ, Semo MJ (1999) J Org Chem 64:5722-4
44. Larock RC, Leung W-Y, Stolz-Dunn S (1989) Tetrahedron Lett 30:6629-6632
45. Guillemont J et al (2005) J Med Chem 48:2072-2079
46. Schils D, Stappers F, Solberghe G, van Heck R, Coppens M, Van den Heuvel D, Van Der Donck P.Callewaert T.Meeussen F.De Bie E.Eersels K.Schouteden E.Donck P, Callewaert T, Meeussen F, De Bie E, Eersels K, Schouteden E (2008) Org Proc Res Dev 12:530-6
47. Singer RA, McKinley JD, Barbe G, Farlow RA (2004) Org Lett 6:2357-60
48. W€ustenberg B, Stemmler RT, Létinois U, Bonrath W, Hugentobler M, Netscher T (2011) Chimia 65:420-8
49. Haerter R, Lemke U, Radspieler A (2005) WO2005/023740, DSM IP Assets B.V., Heerlen
50. Bonrath W, Eggersdorfer M, Netscher T (2007) Catal Today 121:45-57
51. Miyaura N, Suzuki A (1995) Chem Rev 95:2457-83
52. Alonso F, Beletskaya IP, Yus M (2008) Tetrahedron 64:3047-101
53. R€oper M (2006) Chem Unserer Zeit 40:126-35
54. Eicken K, Gebhardt J, Rang H, Rack M, Sch€afer P (1997) WO97/33846, BASF Aktiengesellschaft, Ludwigshafen
55. Engel S, Overding T (2006) WO2006092429, BASF Aktiengesellschaft, Ludwigshafen
56. Haber S, Manero J (1995) EP0694530, Hoechst AG, Frankfurt
57. Debono M, Turner WW, LaGrandeur L, Burkhardt FJ, Nissen JS, Nichols KK, Rodriguez
58. MJ, Zweifel MJ, Zeckner DJ, Gordee RS, Tang J, Parr TR Jr (1995) J Med Chem 38:3271-81
59. Norris T, VanAlsten J, Hubbs S, Ewing M, Cai W, Jorgensen ML, Bordner J, Jensen GO, Org Proc Res Dev 12:447-55
60. Scherer S, Haber S (2000) WO00/50375, Clariant GmbH, Frankfurt am Main, Frankfurt am Main
61. Cui JJ, Tran-Dubé M, Shen H, Nambu M, Kung P-P, Pairish M, Jia L, Meng J, Funk L, Botrous I, McTigue M, Grodsky N, Ryan K, Padrique E, Alton G, Timofeevski S, Yamazaki S, Li Q, Zou H, Christensen J, Mroczkowski B, Bender S, Kania RS, Edwards MP (2011) J Med Chem 54:6342-63
62. de Koning PD, McAndrew D, Moore R, Moses IB, Boyles DC, Kissick K, Stanchina CL, Cuthbertson T, Kamatani A, Rahman L, Rodriguez R, Urbina A, Sandoval (née Accacia) A,
63. Peter Rose R (2011) Org Process Res Dev 15:1018-26
64. Sorbera LA, Revel L, Rabasseda X, Castaner J (2001) Drugs Fut 26:32-8
65. Birari DR, Rao DR, Kankan RN (2011) WO2011/073617, Cipla Ltd., Mumbai
66. Yamamoto T, Muto K, Komiyama M, Canivet J, Yamaguchi J, Itami K (2011) Chem Eur J :10113-22
67. Hayashi K, Takahata M, Kawamura Y, Todo Y (2002) Arzneim Forsch Drug Res 52:903-13
68. Todo Y, Hayashi K, Takahata M, Watanabe Y, Narita H (2000) US Patent 6,025,370, Toyama Chemical Co. Ltd., Tokyo
69. Carter MC, Cockerill GS, Guntrip SB, Lackey KE, Smith KJ (1999) WO99/35146, Glaxo Group Limited, Brentford
70. McClure MS, Osterhout MH, Roschangar F, Sacchetti MJ (2002) WO02/02552, Glaxo Group Limited, Brentford
71. Chen Y-F, Henschke JP, Liu Y, Chu G, Zhang X (2011) WO2011/116634, Scinopharm Taiwan Ltd., Tainan
72. Zhou J, Liu P, Lin Q, Metcalf BW, Meloni D, Pan Y, Xia M, Li M, Yue T-Y, Rodgers JD, Wang H (2010) WO2010/083283, Incyte Corporation, Wilmington
73. Lin Q, Meloni D, Pan Y, Xia M, Rodgers J, Shepard S, Li M, Galya L, Metcalf B, Yue T-Y,Liu P, Zhou J (2009) Org Lett 11:1999-2002
74. Ibrahim P, Artis DR, Bremer R, Mamo S, Nespi M, Zhang C, Zhang J, Zhu Y-L, Tsai J, Hirth K-P, Bollag G, Spevak W, Cho H, Gilette SJ, Wu G, Zhu H, Shi S (2007) WO2007/002325, Plexxikon Inc., Berkeley
75. Hildebrand S, Mair H-J, Radinov RN, Ren Y, Wright JA (2011) WO2011/015522, Hoffmann-La Roche, Basel
76. Ye E, Tan H, Li S, Fan WY (2006) Angew Chem Int Ed 45:1120-3
77. Potter GA, Banie SE, Jarman M, Rowlands MG (1995) J Med Chem 38:2463-71
78. Hunt NJ (2006) WO2006/021776, BTG International Limited, London
79. Potter GA, Hardcastle IR, Jarman M (1997) Org Prep Proc Int 29:123-34
80. Poetsch E (1988) Kontakte (Darmstadt) 15-28
81. Pauluth D, Tarumi K (2004) J Mater Chem 14:1219-27
82. Knappke CEI, Jacobi von Wangelin A (2011) Chem Soc Rev 40:4948-62
83. Geissler H (1998) In: Beller M, Bolm C (eds) Transition metals for organic synthesis, vol 1.
84. Wiley-VCH, Weinheim, pp 158-83
85. Tamao K, Sumitani K, Kumada M (1972) J Am Chem Soc 94:4374-6
86. Corriu RJP, Masse JP (1972) Chem Commun 144
87. Yamamura M, Moritani I, Murahashi S-I (1975) J Organomet Chem 91:C39-42
88. Banno T, Hayakawa Y, Umeno M (2002) J Organomet Chem 653:288-91
89. Giordano C (1995) Abstracts of the conference "selectivity in metal promoted catalytic processes". Peníscola, Spain
90. Giordano C, Coppi L, Minisci F (1994) US Patent 5,312,975, Zambon, Bresso
91. Muhktar S, Nair DS, Medhane RR, Maheshwari N, Tewari N, Prasad N (2011) WO2011/ Ranbaxy Laboratories Limited, Gurgaon
92. BoldG, F€asslerA, CapraroH-G, Cozens R,Klimkait T, Lazdins J,Mestan J, Poncioni B, R€osel J, Stover D, Tintelnot-Blomley M, Acemoglu F, Beck W, Boss E, Eschbach M, H€urlimann T, Masso E, Roussel S, Ucci-Stoll K, Wyss D, Lang M (1998) J Med Chem 41:3387-401
93. Phapale VB, Ca'rdenas DJ (2009) Chem Soc Rev 38:1598-607
94. Negishi E-I (2002) In: Negishi E-I, de Meijere A (eds) Handbook of organopalladium chemistry for organic synthesis, vol 1. Wiley, New York, pp 229-47
95. Charpentier B, Bernardon J-M, Eustache J, Millois C, Martin B, Michel S, Shroot B (1995) J Med Chem 38:4993-5006
96. Miller JA, Farrell RP (1998) Tetrahedron Lett 39:7275-8
97. Doucet H, Hierso J-C (2007) Angew Chem Int Ed 46:834-71
98. Sonogashira K (2002) In: Negishi E-I, de Meijere A (eds) Handbook of organopalladium chemistry for organic synthesis, vol 1. Wiley, New York, pp 493-529
99. Sonogashira K, (2002) J Organomet Chem 653:46-9
100. Cse'kei M, Nova'k Z, Kotschy A (2008) Tetrahedron 64:8992-6
101. Zanardi A, Mata JA, Peris E (2009) Organometallics 28:4335-9
102. Beutler U, Mazacek J, Penn G, Schenkel B, Wasmuth D (1996) Chimia 50:154-6
103. Nakagawa S, Asai A, Kuroyanagi S, Ishihara M, Tanaka Y (1991) EP421302, Banyu Pharmaceutical Co. Ltd, Tokyo
104. Szekeres T, Répási J, Szábo A, Mangion B (2008) WO2008/035212, Medichem, S. A. Sant Joan Despí (Barcelona)
105. Allegrini P, Attolino E, Rossi D (2011) EP2327684, Dipharma Francis S. r. l., Baranzate Milano
106. Strader CR, Pearce CJ, Oberlies NH, Nat (2011) J Nat Prod 74:900-7
107. Adachi K, Kohara T, Nakao N, Afita M, Chiba K, Mishina T, Sasaki S, Fujita T (1995) Bioorg. Med Chem Lett 5:853-6
108. Sedelmeier G (2009) WO2009/115534, Novartis AG, Basel
109. Seidel G, Laurich D, F€urstner A (2004) J Org Chem 69:3950-2
110. Barnett CJ, Wilson TM, Kobierski ME (1999) Org Proc Res Dev 3:184-8
111. Chandraratna RAS (1988) EP0284288, Allergan Inc, Irvine
112. Frigoli S, Fuganti C, Malpezzi L, Serra S (2005) Org Proc Res Dev 9:646-50
113. Borzilleri RM, Zheng X, Schmidt RJ, Johnson JA, Kim S-H, DiMarco JD, Fairchild CR, Gougoutas JZ, Lee FYF, Long BH, Vite GD (2000) J Am Chem Soc 122:8890-7
114. Li WS, Thornton JE, Guo Z, Swaminathan S, McConlogue GW (2001) WO01/70716, Bristol-Myers Squibb, New York
115. Peglion J-L, Baudoin O, Audic N, Chaumontet M, Piccardi R (2010) WO2010/007253, Les Laboratoires Servier, Suresnes
116. Baudoin O, Herrbach A, Gue'ritte F (2003) Angew Chem Int Ed 42:5736-40
117. de Vries JG (2003) In: Horvath IT (ed) Encyclopedia of catalysis, vol 3. Wiley, New York pp 295-347
118. Tucker CE, de Vries JG (2002) Top Catal 19:111-8
119. Allgeier AM, Shaw BJ, Hwang T-L, Milne JE, Tedrow JS, Wilde CN (2012) Organometallics 519-22