The development of a 'safety-catch' arylgermane for biaryl synthesis by palladium-catalysed germyl-Stille cross-coupling

Applied Organometallic Chemistry

Volumn 21, Issue 7, 2007, Pages 572-589

  Spivey, Alan C ^a   Gripton, Christopher J G ^b   Hannah, Joseph P ^a   Tseng, Chih Chung ^a   De Fraine, Paul ^c   Parr, Nigel J ^d   Scicinski, Jan J ^d  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b UNIVERSITY OF SHEFFIELD   (United Kingdom)

^c JEALOTT S HILL INTERNATIONAL RESEARCH CENTRE   (United Kingdom)

^d GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Cross coupling; Fluorous phase; Germanium; Palladium; Photooxidation; Solid phase

Indexed keywords

CATALYST ACTIVITY; CROSSLINKING; PALLADIUM COMPOUNDS; PARAFFINS; PHOTOOXIDATION; SYNTHESIS (CHEMICAL);

CROSS-COUPLING; FLUOROUS-PHASES; SOLID-PHASES;

ORGANOMETALLICS;

EID: 34447314629     PISSN: 02682605     EISSN: 10990739     Source Type: Journal    
DOI: 10.1002/aoc.1270     Document Type: Conference Paper

References (109)

1. Hassan J, Sévignon M, Gozzi C, Schulz E, Lemaire M. Chem. Rev 2002; 102: 1359.
2. Hajduk PJ, Bures M, Praestgaard J, Fesik SW. J. Med. Chem. 2000; 43: 3443.
3. Whitty A, Kumaravel G. Nat. Chem. Biol. 2006; 2: 112.
4. Yin H, Hamilton A. Angew. Chem. Int. Edn 2005; 44: 4130.
5. Suzuki A. Chem. Commun. 2005; 4759.
6. Molander GA, Figueroa R. Aldrichimica Acta 2005; 38: 49.
7. Molander GA, Ellis N. Acc. Chem. Res. 2007; 40: 275.
8. Lessene G. Aust. J. Chem. 2004; 57: 107.
9. Echavarren AM. Angew. Chem. Int. Edn 2005; 44: 3962.
10. Eaborn C, Pande KC. J. Chem. Soc. 1960; 1566.
11. Handy CJ, Manoso AS, McElroy WT,Seganish WM,DeShongP. Tetrahedron 2005; 61: 12201.
12. Denmark SE, Ober MH. Aldrichimica Acta 2003; 36: 75.
13. Hiyama T, Shirakawa E. Top. Curr. Chem. 2002; 219: 61.
14. Denmark SE, Sweis RF. Chem. Pharm. Bull. 2002; 50: 1531.
15. Denmark SE, Sweis RF. Acc. Chem. Res. 2002; 35: 835.
16. Horn KA. Chem. Rev. 1995; 95: 1317.
17. Spivey AC, Gripton CJG, Hannah JP. Curr. Org. Syn. 2004; 1: 211.
18. Denmark SE, Choi JY. J. Am. Chem. Soc. 1999; 121: 5821.
19. Denmark SE, Neuville L. Org. Lett. 2000; 2: 3221.
20. Yoshida J-i, Itami K, Mitsudo K, Suga S. Tetrahedron Lett. 1999; 40: 3403.
21. Itami K, Nokami T, Yoshida J-i. J. Am. Chem. Soc. 2001; 123: 5600.
22. Itami K, Kamei T, Yoshida J-i. J. Am. Chem. Soc. 2001; 123: 8773.
23. Itami K, Nokami T, Ishimura Y, Mitsudo K, Kamei T, Yoshida J-i. J. Am. Chem. Soc. 2001; 123: 11577.
24. Itami K, Mitsudo K, Nokami T, Kamei T, Koike T, Yoshida J-i. J. Organomet. Chem. 2002; 653: 105.
25. Itami K, Mineno M, Kamei T, Yoshida J-i. Org. Lett. 2002; 4: 3635.
26. Itami K, Kamei T, Yoshida J-i. J. Am. Chem. Soc. 2003; 125: 14670.
27. Nokami T, Tomida Y, Kamei T, Itami K, Yoshida J-i. Org. Lett. 2006; 8: 729.
28. Hosoi K, Nozaki K, Hiyama T. Chem. Lett. 2002; 138.
29. Katayama H, Nagao M, Moriguchi R, Ozawa F. J. Organomet. Chem. 2003; 676: 49.
30. Katayama H, Taniguchi K, Kobayashi M, Sagawa T, Minami T, Ozawa F. J. Organomet. Chem. 2002; 645: 192.
31. Trost BM, Machacek MR, Ball ZT. Org. Lett. 2003; 5: 1895.
32. Denmark SE, Tymonko SA. J. Am. Chem. Soc. 2005; 127: 8004.
33. Denmark SE, Fujimori S. J. Am. Chem. Soc. 2005; 127: 8971.
34. Anderson JC, Munday RH. J. Org. Chem. 2004; 69: 8971.
35. Horino Y, Luzung MR, Toste FD. J. Am. Chem. Soc. 2006; 128: 11364.
36. Nakao Y, Oda T, Sahoo AK, Hiyama T. J. Organomet. Chem. 2003; 687: 570.
37. Sahoo AK, Oda T, Nakao Y, Hiyama T. Adv. Synth. Catal. 2004; 346: 1715.
38. Sahoo AK, Nakao Y, Hiyama T. Chem. Lett. 2004; 33: 632.
39. Dandapani S, Curran DP, Ley SV, Massi A, Rodriguez F, Harwell DC, Lewthwaite RA, Pritchard MC, Reid AM, Zhang SQ, Fukase K, Izumi M, Fukase Y, Kusumoto S, Bosanac T, Yang J, Wilcox CS. Chemtracts: Org. Chem. 2001; 14: 635.
40. Krchnák V, Holladay MW. Chem. Rev. 2002; 102: 61.
41. Zhang W. Chem. Rev. 2004; 104: 2531.
42. Curran DP. Angew. Chem. Int. Edn 1998; 37: 1174.
43. Allred AL, Rochow EG. J. Inorg. Nucl. Chem. 1958; 5: 269.
44. Pyykkö P. Int. J. Quant. Chem. 2001; 85: 18.
45. Basch H, Hoz T. The Nature of the C-M Bond (M = Ge, Sn, Pb). In The Chemistry of Organic Germanium, Tin and Lead Compounds, Patai S (ed.). Wiley: Chichester, 1995.
46. Ikenaga K, Matsumoto S, Kikukawa K, Matsuda T. Chem. Lett. 1990; 2: 185.
47. Kosugi M, Tanji T, Tanaka Y, Yoshida A, Fugami K, Kameyama M, Migita T. J. Organometal. Chem. 1996; 508: 255.
48. Nakamura T, Kinoshita H, Shinokubo H, Oshima K. Org. Lett. 2002; 4: 3165.
49. Yorimitsu H, Oshima K. Inorg. Chem. Commun. 2005; 8: 131.
50. Faller JW, Kultyshev RG. Organometallics 2002; 21: 5911.
51. Faller JW, Kultyshev RG. Organometallics 2003; 22: 199.
52. Faller JW, Kultyshev RG, Parr J. Tetrahedron Lett. 2003; 44: 451.
53. Kultyshev RG, Prakash SGK, Olah GA, Faller JW, Parr J. Organometallics 2004; 23: 3184.
54. Wnuck SF, Garcia PI, Wang Z. Org. Lett. 2004; 6: 2047.
55. Wang ZH, Wnuk SF. J. Org. Chem. 2005; 70: 3281.
56. Wang Z, Gonzalez A, Wnuck SF. Tetrahedron Lett. 2005; 46: 5313.
57. Enokido T, Fugami K, Endo M, Keameyama M, Kosugi M. Adv. Synth. Catal. 2004; 346: 1685.
58. Karlov SS, Zaitseva GS. Chem. Met. Comp. 2001; 37: 1325.
59. Verkade JG. Coord. Chem. Rev. 1994; 137: 233.
60. Spivey AC, Gripton CJG, Hannah JP. Curr. Org. Synth 2004; 1: 211.
61. Spivey AC, Diaper CM, Adams H, Rudge AJ. J. Org. Chem. 2000; 65: 5253.
62. Spivey AC, Srikaran R, Diaper CM, Turner DJ. Org. Biomol. Chem. 2003; 1: 1638.
63. Spivey AC, Turner DJ, Turner ML, Yeates S. Org. Lett. 2002; 4: 1899.
64. Spivey AC, Turner DJ, Turner ML, Yeates S. Synlett 2004; 111.
65. Spivey AC, Gripton CJG, Noban C, Parr NJ. Synlett 2005; 2167.
66. Scott PJH, Steel PG. Eu. J. Org. Chem. 2006; 2251.
67. Vanier C, Lorge F, Wagner A, Mioskowski C. Angew. Chem. Int. Edn 2000; 39: 1679.
68. Pan Y, Homles CP. Org. Lett. 2001; 3: 2769.
69. Pan Y, Ruhland B, Holmes CP. Angew. Chem. Int. Edn 2001; 40: 4488.
70. Cammidge AN, Ngaini Z. Chem. Commun. 2004; 1914.
71. Revell JD, Ganesan A. Chem. Commun. 2004; 1916.
72. Cho C-H, Park H, Park M-A, Ryoo T-Y, Lee Y-S, Park K. Eur. J. Org. Chem. 2005; 3177.
73. Tsukamoto H, Suzuki R, Kondo Y. J. Comb. Chem 2006; 8: 289.
74. Campbell IB, Guo J, Jones E, Steel PG. Org. Biomol. Chem. 2004; 2725.
75. Zhang W, Curran DP. Tetrahedron 2006; 62: 11837.
76. Nicolaou KC, Winssinger N, Pastor J, Murphy F. Angew. Chem. Int. Edn 1998; 37: 2534.
77. Li W, Burgess K. Tetrahedron Lett. 1999; 40: 6527.
78. Huang Y, Qing F-L. QSAR Comb. Sci. 2006; 25: 716.
79. Hatanaka Y, Fukushima S, Hiyama T. Chem. Lett. 1989; 1711.
80. Hatanaka Y, Goda K, Hiyama T, Okahara Y. Tetrahedron 1994; 50: 8301.
81. Hagiwara E, Gouda K-i, Hatanaka Y, Hiyama T. Tetrahedron Lett. 1997; 38: 439.
82. Nakamura T, Yorimitsu H, Shinokubo H, Oshima K. Tetrahedron 2001; 57: 9827.
83. Kaye S, Fox JM, Hicks FA, Buchwald SL. Adv. Synth. Catal. 2001; 343: 789.
84. Tamao K, Ishida N. Tetrahedron Lett. 1984; 25: 4249.
85. Hatanaka Y, Hiyama T. J. Org. Chem. 1989; 54: 268.
86. Trost BM, Machacek MR, Faulk BD. J. Am. Chem. Soc. 2006; 128: 6745.
87. Denmark SE, Liu JH-C. J. Am. Chem. Soc. 2007; 129: 3737.
88. Yoshida J-i, Nishiwaki K. J. Chem. Soc., Dalton Trans. 1998; 2589.
89. Dinnocenzo JP, Farid S, Goodman JL, Gould IR, Todd WP, Mattes SL. J. Am. Chem. Soc. 1989; 111: 8973.
90. Baciocchi E, Giacco TD, Rol C, Sebastiani GV. Tetraherdron Lett. 1989; 30: 3573.
91. Mizuno K, Yasueda M, Otsuji Y. Chem. Lett. 1988; 229.
92. Maruyama T, Mizuno Y, Shimizu I, Suga S, Yoshida J-i. J. Am. Chem. Soc. 2007; 129: 1902.
93. Li J-H, Deng C-L, Xie Y-X. Synthesis 2006; 969.
94. Mee SPH, Lee V, Baldwin JE. Chem. Eur. J. 2005; 11: 3294.
95. Mee SPH, Lee V, Baldwin JE. Angew. Chem., Int. Edn 2004; 43: 1132.
96. Still WC, Kahn M, Mitra A. J. Org. Chem. 1978; 43: 2923.
97. Brune HA, Hess R, Schmidtberg G. Zeit. Naturfor. B: Anorg. Chem. Org. Chem. 1984; 39B: 1772.
98. Ueda M, Saitoh A, Oh-Tani S, Miyaura N. Tetrahedron 1998; 54: 13079.
99. Thompson NJ, Gray GW, Goodby JW, Toyne KJ. Mol. Cryst. Liq. Cryst. 1991; 200: 109.
100. Byron DJ, Gray GW, Wilson RC. J. Chem. Soc. C 1966; 840.
101. Nishimura M, Ueda M, Miyaura N. Tetrahedron 2002; 58: 5779.
102. Brune HA, Ertl J. Liebigs Ann.Chem. 1980; 928.
103. Darses S, Jeffery T, Brayer J-L, Demoute J-P, Genet J-P. Bull. Soc. Chim. Fr. 1996; 133: 1095.
104. Badone D, Baroni M, Cardamone R, Ielmini A, Guzzi U. J. Org. Chem. 1997; 62: 7170.
105. Kobayashi Y, William AD, Mizojiri R. J. Organomet. Chem. 2002; 653: 91.
106. Leznoff CC, Hayward RJ. Can. J. Chem. 1970; 48: 1842.
107. Ishikura M, Kamada M, Terashima M. Heterocycles 1984; 22: 265.
108. Mori Y, Seki M. J. Org. Chem. 2003; 68: 1571.
109. Denmark SE, Ober MH. Org. Lett. 2003; 5: 1357.