Recent advances in metal-catalyzed C-P bond formation

Topics in Organometallic Chemistry

Volumn 31, Issue , 2010, Pages 65-100

  Glueck, David S ^a  

^a Dartmouth College   (United States)

Author keywords

Cross coupling; Hydrophosphination; Mechanism; Palladium; Phosphination; Phosphine

Indexed keywords

EID: 77954601024     PISSN: 14366002     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-3-642-12073-2_4     Document Type: Article

References (126)

1. Baillie C, Xiao JL (2003) Curr Org Chem 7:477-514
2. Beletskaya IP, Kazankova MA (2002) Russ J Org Chem 38:1391-1430
3. Coudray L, Montchamp J-L (2008) Eur J Org Chem:3601-3613
4. Delacroix O, Gaumont A-C (2005) Curr Org Chem 9:1851-1882
5. Montchamp J-L (2005) J Organomet Chem 690:2388-2406
6. Tanaka M (2004) Top Curr Chem 232:25-54
7. Wicht DK, Glueck DS (2001) In: Togni A, Grutzmacher H (eds) Catalytic heterofunctionalization. Wiley-VCH, Weinheim pp 143-170
8. Dobashi N, Fuse K, Hoshino T, Kanada J, Kashiwabara T, Kobata C, Nune SK, Tanaka M (2007) Tetrahedron Lett 48:4669-4673
9. Nune SK, Tanaka M (2007) Chem Commun:2858-2860
10. Han L-B, Ono Y, Yazawa H (2005) Org Lett 7:2909-2911
11. Han L-B, Huang Z, Matsuyama S, Ono Y, Zhao C-Q (2005) J Polym Sci A Polym Chem 43:5328-5336
12. Rooy SV, Cao C, Patrick BO, Lam A, Love JA (2006) Inorg Chim Acta 359:2918-2923
13. Duraud A, Toffano M, Fiaud J-C (2009) Eur J Org Chem 2009:4400-4403
14. Join B, Mimeau D, Delacroix O, Gaumont A-C (2006) Chem Commun:3249-3251
15. Ananikov VP, Khemchyan LL, Beletskaya IP (2009) Synlett 2375-2381
16. Niu M, Fu H, Jiang Y, Zhao Y (2007) Chem Commun 272-274
17. Gao Y, Wang G, Chen L, Xu P, Zhao Y, Zhou Y, Han L-B (2009) J Am Chem Soc 131:7956-7957
18. Han L-B, Ono Y, Shimada S (2008) J Am Chem Soc 130:2752-2753
19. Mizuta T, Miyaji C, Katayama T, Ushio J, Kubo K, Miyoshi K (2009) Organometallics 28:539-546
20. Nagata S, Kawaguchi S, Matsumoto M, Kamiya I, Nomoto A, Sonoda M, Ogawa A (2007) Tetrahedron Lett 48:6637-6640
21. Kawaguchi S, Nagata S, Nomoto A, Sonoda M, Ogawa A (2008) J Org Chem 73:7928-7933
22. Xu Q, Han L-B (2006) Org Lett 8:2099-2101
23. Barta K, Francio G, Leitner W, Lloyd-Jones GC, Shepperson IR (2008) Adv Synth Catal 350:2013-2023
24. Shulyupin MO, Franciu G, Beletskaya IP, Leitner W (2005) Adv Synth Catal 347:667-672
25. Alnasleh BK, Sherrill WM, Rubin M (2008) Org Lett 10:3231-3234
26. Ajellal N, Guillevic E, Thomas CM, Jackstell R, Beller M, Carpentier J-F (2008) Adv Synth Catal 350:431-438
27. Ajellal N, Thomas CM, Carpentier J-F (2006) Adv Synth Catal 348:1093-1100
28. Hirai T, Han L-B (2006) J Am Chem Soc 128:7422-7423
29. Crimmin MR, Barrett AGM, Hill MS, Hitchcock PB, Procopiou PA (2007) Organometallics 26:2953-2956
30. Motta A, Fragala IL, Marks TJ (2005) Organometallics 24:4995-5003
31. Kawaoka AM, Marks TJ (2005) J Am Chem Soc 127:6311-6324
32. Kawaoka AM, Marks TJ (2004) J Am Chem Soc 126:12764-12765
33. Mercy M, Maron L (2009) Dalton Trans 3014-3025
34. Al-Shboul TMA, Gorls H, Westerhausen M (2008) Inorg Chem Commun 11:1419-1421
35. Komeyama K, Kobayashi D, Yamamoto Y, Takehira K, Takaki K (2006) Tetrahedron 62:2511-2519
36. Komeyama K, Kawabata T, Takehira K, Takaki K (2005) J Org Chem 70:7260-7266
37. Crimmin MR, Barrett AGM, Hill MS, Hitchcock PB, Procopiou PA (2008) Organometallics 27:497-499
38. Al-Shboul TMA, Volland G, Gorls H, Westerhausen M (2009) Z Anorg Allg Chem 635:1568-1572
39. Zhang W-X, Nishiura M, Hou Z (2006) Chem Commun:3812-3814
40. Zhang W-X, Nishiura M, Mashiko T, Hou Z (2008) Chem Eur J 14:2167-2179
41. Zhang W-X, Hou Z (2008) Org Biomol Chem 6:1720-1730
42. Zhao G, Basuli F, Kilgore UJ, Fan H, Aneetha H, Huffman JC, Wu G, Mindiola DJ (2006) J Am Chem Soc 128:13575-13585
43. Glueck DS (2008) Dalton Trans 5276-5286
44. Scriban C, Kovacik I, Glueck DS (2005) Organometallics 24:4871-4874
45. Scriban C, Glueck DS, Zakharov LN, Kassel WS, DiPasquale AG, Golen JA, Rheingold AL (2006) Organometallics 25:5757-5767
46. Kovacik I, Scriban C, Glueck DS (2006) Organometallics 25:536-539
47. Yao Q (2007) Tetrahedron Lett 48:2749-2753
48. Greenberg S, Gibson GL, Stephan DW (2009) Chem Commun:304-306
49. Greenberg S, Stephan DW (2009) Inorg Chem 48:8623-8631
50. Lemmen TH, Goeden GV, Huffman JC, Geerst RL, Caulton KG (1990) Inorg Chem 29:3680-3685
51. Kondoh A, Yorimitsu H, Oshima K (2007) J Am Chem Soc 129:4099-4104
52. Ohmiya H, Yorimitsu H, Oshima K (2005) Angew Chem Int Ed Engl 44:2368-2370
53. Sadow AD, Togni A (2005) J Am Chem Soc 127:17012-17024
54. Sadow AD, Haller I, Fadini L, Togni A (2004) J Am Chem Soc 126:14704-14705
55. Kazankova MA, Shulyupin MO, Beletskaya IP (2003) Synlett 2155-2158
56. Shulyupin MO, Trostyanskaya IG, Kazankova MA, Beletskaya IP (2006) Russ J Org Chem 42:17-22
57. Jérome F, Monnier F, Lawicka H, Dérien S, Dixneuf PH (2003) Chem Commun:696-697
58. Kumaraswamy G, Venkata Rao G, RamaKrishna G (2006) Synlett 1122-1124
59. Merino P, Marques-Lopez E, Herrera RP (2008) Adv Synth Catal 350:1195-1208
60. Yang F, Zhao D, Lan J, Xi P, Yang L, Xiang S, You J (2008) Angew Chem Int Ed Engl 47:5646-5649
61. Gou S, Zhou X, Wang J, Liu X, Feng X (2008) Tetrahedron 64:2864-2870
62. Rai V, Namboothiri INN (2008) Tetrahedron Asymmetry 19:2335-2338
63. Zhao D, Yuan Y, Chan ASC, Wang R (2009) Chem Eur J 15:2738-2741
64. Schwan AL (2004) Chem Soc Rev 33:218-224
65. Tunney SE, Stille JK (1987) J Org Chem 52:748-753
66. Nechab M, Le Gall E, Troupel M, Nedelec J-Y (2006) J Organomet Chem 691:1809-1813
67. Gelman D, Jiang L, Buchwald SL (2003) Org Lett 5:2315-2318
68. Van Allen D, Venkataraman D (2003) J Org Chem 68:4590-4593
69. Huang C, Tang X, Fu H, Jiang Y, Zhao Y (2006) J Org Chem 71:5020-5022
70. Tye JW, Weng Z, Johns AM, Incarvito CD, Hartwig JF (2008) J Am Chem Soc 130:9971-9983
71. Tani K, Behenna DC, McFadden RM, Stoltz BM (2007) Org Lett 9:2529-2531
72. Glueck DS (2007) Synlett 2627-2634
73. Glueck DS (2008) Coord Chem Rev 252:2171-2179
74. Glueck DS (2008) Chem Eur J 14:7108-7117
75. Blank NF, Moncarz JR, Brunker TJ, Scriban C, Anderson BJ, Amir O, Glueck DS, Zakharov LN, Golen JA, Incarvito CD, Rheingold AL (2007) J Am Chem Soc 129:6847-6858
76. Korff C, Helmchen G (2004) Chem Commun:530-531
77. Blank NF, McBroom KC, Glueck DS, Kassel WS, Rheingold AL (2006) Organometallics 25:1742-1748
78. Chan VS, Bergman RG, Toste FD (2007) J Am Chem Soc 129:15122-15123
79. Brunker TJ, Anderson BJ, Blank NF, Glueck DS, Rheingold AL (2007) Org Lett 9:1109-1112
80. Murata M, Buchwald SL (2004) Tetrahedron 60:7397-7403
81. Shulyupin MO, Chirkov EA, Kazankova MA, Beletskaya IP (2005) Synlett 658-660
82. Thielges S, Bisseret P, Eustache J (2005) Org Lett 7:681-684
83. Clarke ML, Orpen AG, Pringle PG, Turley E (2003) Dalton Trans 4393-4394
84. Lanteri MN, Rossi RA, Martin SE (2009) J Organomet Chem 694:3425-3430
85. Bonaterra M, Rossi RA, Martin SE (2009) Organometallics 28:933-936
86. Butti P, Rochat R, Sadow AD, Togni A (2008) Angew Chem Int Ed 47:4878-4881
87. Trepohl VT, Frohlich R, Oestreich M (2009) Tetrahedron 65:6510-6518
88. Trepohl VT, Oestreich M (2007) Chem Commun:3300-3302
89. Trepohl VT, Mori S, Itami K, Oestreich M (2009) Org Lett 11:1091-1094
90. Hayashi M, Matsuura Y, Watanabe Y (2006) J Org Chem 71:9248-9251
91. Coudray L, Bravo-Altamirano K, Montchamp J-L (2008) Org Lett 10:1123-1126
92. Coudray L, Montchamp J-L (2008) Eur J Org Chem 2008:4101-4103
93. Vallette H, Pican S, Boudou C, Levillain J, Plaquevent J-C, Gaumont A-C (2006) Tetrahedron Lett 47:5191-5193
94. Pican S, Gaumont A-C (2005) Chem Commun:2393-2395
95. Moncarz JR, Brunker TJ, Jewett JC, Orchowski M, Glueck DS, Sommer RD, Lam K-C, Incarvito CD, Concolino TE, Ceccarelli C, Zakharov LN, Rheingold AL (2003) Organometallics 22:3205-3221
96. Moncarz JR, Brunker TJ, Glueck DS, Sommer RD, Rheingold AL (2003) J Am Chem Soc 125:1180-1181
97. Pirat J-L, Monbrun J, Virieux D, Cristau H-J (2005) Tetrahedron 61:7029-7036
98. Laven G, Stawinski J (2009) Synlett 2009:225-228
99. Kalek M, Stawinski J (2007) Organometallics 26:5840-5847
100. Kalek M, Stawinski J (2008) Organometallics 27:5876-5888
101. Kohler MC, Sokol JG, Stockland RA Jr (2009) Tetrahedron Lett 50:457-459
102. Kohler MC, Grimes TV, Wang X, Cundari TR, Stockland RA Jr (2009) Organometallics 28:1193-1201
103. Marcoux D, Charette AB (2008) J Org Chem 73:590-593
104. Marcoux D, Charette AB (2008) Adv Synth Catal 350:2967-2974
105. Kwong FY, Lai CW, Yu M, Chan KS (2004) Tetrahedron 60:5635-5645
106. Goodson FE, Wallow TI, Novak BM (1997) J Am Chem Soc 119:12441-12453
107. Bessmertnykh A, Douaihy CM, Guilard R (2009) Chem Lett 38:738-739
108. Arisawa M, Yamaguchi M (2006) J Am Chem Soc 128:50-51
109. Arisawa M, Yamaguchi M (2000) J Am Chem Soc 122:2387-2388
110. Yao Q, Levchik S (2006) Tetrahedron Lett 47:277-281
111. Adam MSS, Kindermann MK, Kockerling M, Heinicke JW (2009) Eur J Org Chem 2009:4655-4665
112. Scriban C, Glueck DS (2006) J Am Chem Soc 128:2788-2789
113. Scriban C, Glueck DS, Golen JA, Rheingold AL (2007) Organometallics 26:1788-1800
114. (Addition/Correction (2007) Organometallics 26:5124)
115. Chan VS, Stewart IC, Bergman RG, Toste FD (2006) J Am Chem Soc 128:2786-2787
116. Anderson BJ, Glueck DS, DiPasquale AG, Rheingold AL (2008) Organometallics 27:4992-5001
117. (Addition/Correction (2009) Organometallics 28:386)
118. Anderson BJ, Guino-o MA, Glueck DS, Golen JA, DiPasquale AG, Liable-Sands LM, Rheingold AL (2008) Org Lett 10:4425-4428
119. Chan VS, Chiu M, Bergman RG, Toste FD (2009) J Am Chem Soc 131:6021-6032
120. Nishibayashi Y, Milton MD, Inada Y, Yoshikawa M, Wakiji I, Hidai M, Uemura S (2005) Chem Eur J 11:1433-1451
121. Milton MD, Onodera G, Nishibayashi Y, Uemura S (2004) Org Lett 6:3993-3995
122. Onodera G, Matsumoto H, Milton MD, Nishibayashi Y, Uemura S (2005) Org Lett 7:4029-4032
123. Baslé O, Li C-J (2009) Chem Commun 4124-4126
124. Kumaraswamy G, Rao GV, Murthy AN, Sridhar B (2009) Synlett 1180-1184
125. Beletskaya IP, Afanasiev VV, Efimova IV (2003) Org Lett 5:4309-4311
126. Afanasiev VV, Beletskaya IP, Kazankova MA, Efimova IV, Antipin MU (2003) Synthesis: 2835-2838