Nickel N-heterocyclic carbene-catalyzed C-C bond formation: Reactions and mechanistic aspects

ACS Catalysis

Volumn 5, Issue 2, 2015, Pages 1283-1302

  Henrion, Mickaël ^a   Ritleng, Vincent ^a   Chetcuti, Michael J ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

C C bond formation; catalysis; N heterocyclic carbene; nickel; reaction mechanism

Indexed keywords

CATALYSIS; CHEMICAL BONDS; COUPLINGS; COVALENT BONDS; NICKEL;

C-C BOND FORMATION; C-C CROSS-COUPLINGS; CH-BOND ACTIVATION; MECHANISTIC ASPECTS; MECHANISTIC DATA; N-HETEROCYCLIC CARBENE COMPLEX; N-HETEROCYCLIC CARBENES; REACTION MECHANISM;

ORGANIC COMPOUNDS;

EID: 84923164061     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs5014927     Document Type: Article

References (165)

1. Ziegler, K.; Holzkamp, E.; Breil, H.; Martin, H. Angew. Chem. 1955, 67, 541-547 10.1002/ange.19550671902
2. Jolly, J. P.; Wilke, G. The Organic Chemistry of Nickel; Academic Press: New York, 1974.
3. Bini, L.; Müller, C.; Vogt, D. ChemCatChem 2010, 2, 590-608 10.1002/cctc.201000034
4. Bini, L.; Müller, C.; Vogt, D. Chem. Commun. 2010, 46, 8325-8334 10.1039/c0cc01452d
5. Keim, W. Angew. Chem., Int. Ed. 2013, 52, 12492-12496 10.1002/anie.201305308
6. Kuhn, P.; Sémeril, D.; Matt, D.; Chetcuti, M. J.; Lutz, P. Dalton Trans. 2007, 515-528 10.1039/b615259g
7. European Commission. Report on Critical Raw Materials for the EU. May 2014. http://ec.europa.eu/enterprise/policies/raw-materials/files/docs/crm-report-on-critical-raw-materials-en.pdf (accessed October 27, 2014).
8. For an excellent overview of recent advances in homogeneous nickel catalysis: Tasker, S. Z.; Standley, E. A.; Jamison, T. F. Nature 2014, 509, 299-309 10.1038/nature13274
9. Arduengo, A. J., III; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361-363 10.1021/ja00001a054
10. Benhamou, L.; Chardon, E.; Lavigne, G.; Bellemin-Laponnaz, S.; César, V. Chem. Rev. 2011, 111, 2705-2733 10.1021/cr100328e
11. Frenkin, G.; Solà, M.; Vyboishchikov, S. F. J. Organomet. Chem. 2005, 690, 6178-6204 10.1016/j.jorganchem.2005.08.054
12. Radius, U.; Bickelhaupt, F. M. Coord. Chem. Rev. 2009, 253, 678-686 10.1016/j.ccr.2008.05.020
13. Jacobsen, H.; Correa, A.; Poater, A.; Costabile, C.; Cavallo, L. Coord. Chem. Rev. 2009, 253, 687-703 10.1016/j.ccr.2008.06.006
14. Dröge, T.; Glorius, F. Angew. Chem., Int. Ed. 2010, 49, 6940-6952 10.1002/anie.201001865
15. Nelson, D. J.; Nolan, S. P. Chem. Soc. Rev. 2013, 42, 6723-6753 10.1039/c3cs60146c
16. N-Heterocyclic Carbenes in Transition Metal Catalysis; Glorius, F., Eds; Topics in Organometallic Chemistry; Springer-Verlag: Heidelberg, 2007; Vol. 21.
17. Díez-González, S.; Marion, N.; Nolan, S. P. Chem. Rev. 2009, 109, 3612-3676 10.1021/cr900074m
18. Hopkinson, M. N.; Richter, C.; Schedler, M.; Glorius, F. Nature 2014, 510, 485-496 10.1038/nature13384
19. Louie, J. Ni-NHC mediated catalysis. In N-Heterocyclic Carbenes in Synthesis; Nolan, S. P., Eds; Wiley-VCH: Weinheim, 2006; pp 163-182.
20. Gu, S.; Ni, P.; Chen, W. Chin. J. Catal. 2010, 31, 875-886 10.1016/S1872-2067(09)60089-9
21. Fort, Y.; Comoy, C. NHC-Nickel and Platinum complexes. In N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient Synthetic Tools; Díez-González, S., Eds.; RSC Catalysis Series No. 6; RSC Publishing: Cambridge, 2011; pp 284-326.
22. st ed.; Nolan, S. P., Eds.; Wiley-VCH: Weinheim, 2014; pp 371-396.
23. Tamao, K.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 4374-4376 10.1021/ja00767a075
24. Corriu, R. J. P.; Masse, J. P. J. Chem. Soc., Chem. Commun. 1972, 144a-144a 10.1039/c3972000144a
25. Tamao, K. J. Organomet. Chem. 2002, 653, 23-26 10.1016/S0022-328X(02)01159-2
26. Knochel, P.; Sapountzis, I.; Gommermann, N. Carbon-Carbon Bond-Forming Reactions Mediated by Organomagnesium Reagents. In Metal-Catalyzed Cross-Coupling Reactions, 2 nd ed.; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004; pp 671-698.
27. Adrio, J.; Carretero, J. C. ChemCatChem 2010, 2, 1384-1386 10.1002/cctc.201000237
28. Heravi, M. M.; Hajiabbasi, P. Monatsh. Chem. 2012, 143, 1575-1592 10.1007/s00706-012-0838-x
29. de Vries, J. G. Top. Organomet. Chem. 2012, 42, 1-34 10.1007/3418-2012-32
30. Böhm, V. P. W.; Weskamp, T.; Gstöttmayr, C. W. K.; Herrmann, W. A. Angew. Chem., Int. Ed. 2000, 39, 1602-1604 10.1002/(SICI)1521-3773(20000502)39:9<1602::AID-ANIE1602>3.0.CO;2-N
31. Böhm, V. P. W.; Gstöttmayr, C. W. K.; Weskamp, T.; Herrmann, W. A. Angew. Chem., Int. Ed. 2001, 40, 3387-3389 10.1002/1521-3773(20010917)40:18<3387::AID-ANIE3387>3.3.CO;2-Y
32. Kim, C.-B.; Jo, H.; Ahn, B.-K.; Kim, C. K.; Park, K. J. Org. Chem. 2009, 74, 9566-9569 10.1021/jo902151h
33. Jo, H.; Kim, C.-B.; Ryoo, T.-Y.; Ahn, B.-K.; Park, K.-Y. Bull. Korean Chem. Soc. 2010, 31, 3749-3754 10.5012/bkcs.2010.31.12.3749
34. Mitsudo, K.; Doi, Y.; Sakamoto, S.; Murakami, H.; Mandai, H.; Suga, S. Chem. Lett. 2011, 40, 936-938 10.1246/cl.2011.936
35. Wolf, J.; Labande, A.; Daran, J.-C.; Poli, R. J. Organomet. Chem. 2006, 691, 433-443 10.1016/j.jorganchem.2005.09.010
36. Wolf, J.; Labande, A.; Natella, M.; Daran, J.-C.; Poli, R. J. Mol. Catal. A 2006, 259, 205-212 10.1016/j.molcata.2006.06.004
37. Xu, Y.-C.; Zhang, J.; Sun, H.-M.; Shen, Q.; Zhang, Y. Dalton Trans. 2013, 42, 8437-8445 10.1039/c3dt00086a
38. Hatakeyama, T.; Hashimoto, S.; Ishizuka, K.; Nakamura, M. J. Am. Chem. Soc. 2009, 131, 11949-11963 10.1021/ja9039289
39. Şahin, N.; Sémeril, D.; Brenner, E.; Matt, D.; Özdemir, I.; Kaya, C.; Toupet, L. Eur. J. Org. Chem. 2013, 4443-4449 10.1002/ejoc.201300347
40. Joshi-Pangu, A.; Biscoe, M. R. Synlett 2012, 23, 1103-1107 10.1055/s-0031-1290765
41. Lohre, C.; Dröge, T.; Wang, C.; Glorius, F. Chem.-Eur. J. 2011, 17, 6052-6055 10.1002/chem.201100909
42. Joshi-Pangu, A.; Wang, C.-Y.; Biscoe, M. R. J. Am. Chem. Soc. 2011, 133, 8478-8481 10.1021/ja202769t
43. Phapale, V. B.; Guisán-Ceinos, M.; Buñuel, E.; Cárdenas, D. J. Chem.-Eur. J. 2009, 15, 12681-12688 10.1002/chem.200901913
44. Anderson, T. J.; Jones, G. D.; Vicic, D. A. J. Am. Chem. Soc. 2004, 126, 8100-8101 10.1021/ja0483903
45. Jones, G. D.; Martin, J. L.; McFarland, C.; Allen, O. R.; Hall, R. E.; Haley, A. D.; Brandon, R. J.; Konovalova, T.; Desrochers, P. J.; Pulay, P.; Vicic, D. A. J. Am. Chem. Soc. 2006, 128, 13175-13183 10.1021/ja063334i
46. Kashin, A. S.; Ananikov, V. P. J. Org. Chem. 2013, 78, 11117-11125 10.1021/jo402038p
47. Kremzow, D.; Seidel, G.; Lehmann, C. W.; Fürstner, A. Chem.-Eur. J. 2005, 11, 1833-1853 10.1002/chem.200400928
48. Schneider, S. K.; Rentzsch, C. F.; Krüger, A.; Raubenheimer, H. G.; Herrmann, W. A. J. Mol. Catal. A 2007, 265, 50-58 10.1016/j.molcata.2006.09.039
49. Matsubara, K.; Ueno, K.; Shibata, Y. Organometallics 2006, 25, 3422-3427 10.1021/om0602658
50. Liu, Z.-h.; Xu, Y.-C.; Xie, L.-Z.; Sun, H.-M.; Shen, Q.; Zhang, Y. Dalton Trans. 2011, 40, 4697-4706 10.1039/c1dt10077g
51. Miyazaki, S.; Koga, Y.; Matsumoto, T.; Matsubara, K. Chem. Commun. 2010, 46, 1932-1934 10.1039/b924716e
52. Zhang, K.; Conda-Sheridan, M.; Cooke, S. R.; Louie, J. Organometallics 2011, 30, 2546-2552 10.1021/om200090d
53. Nagao, S.; Matsumoto, T.; Koga, Y.; Matsubara, K. Chem. Lett. 2011, 40, 1036-1038 10.1246/cl.2011.1036
54. Page, M. J.; Lu, W. Y.; Poulten, R. C.; Carter, E.; Algarra, A. G.; Kariuki, B. M.; Macgregor, S. A.; Mahon, M. F.; Cavell, K. J.; Murphy, D. M.; Whittlesey, M. K. Chem.-Eur. J. 2013, 19, 2158-2167 10.1002/chem.201202950
55. Jothibasu, R.; Huang, K.-W.; Huynh, H. V. Organometallics 2010, 29, 3746-3752 10.1021/om100241v
56. Macklin, T. K.; Snieckus, V. Org. Lett. 2005, 7, 2519-2522 10.1021/ol050393c
57. Iglesias, M. J.; Prieto, A.; Nicasio, M. C. Org. Lett. 2012, 14, 4318-4321 10.1021/ol302112q
58. Iglesias, M. J.; Prieto, A.; Nicasio, M. C. Adv. Synth. Catal. 2010, 352, 1949-1954 10.1002/adsc.201000223
59. Marion, N.; Navarro, O.; Mei, J.; Stevens, E. D.; Scott, N. M.; Nolan, S. P. J. Am. Chem. Soc. 2006, 128, 4101-4111 10.1021/ja057704z
60. Navarro, O.; Marion, N.; Mei, J.; Nolan, S. P. Chem.-Eur. J. 2006, 12, 5142-5148 10.1002/chem.200600283
61. Tennyson, A. G.; Lynch, V. M.; Bielawski, C. W. J. Am. Chem. Soc. 2010, 132, 9420-9429 10.1021/ja102686u
62. Xi, Z.; Liu, B.; Chen, W. J. Org. Chem. 2008, 73, 3954-3957 10.1021/jo800197u
63. Gu, S.; Chen, W. Organometallics 2009, 28, 909-914 10.1021/om801056v
64. Sun, Y.; Li, X.; Sun, H. Dalton Trans. 2014, 43, 9410-9413 10.1039/c4dt00461b
65. Chen, C.; Qiu, H.; Chen, W. J. Organomet. Chem. 2012, 696, 4166-4172 10.1016/j.jorganchem.2011.09.008
66. Inamoto, K.; Kuroda, J.-i.; Sakamoto, T.; Hiroya, K. Synthesis 2007, 2853-2861 10.1055/s-2007-983845
67. MaGee, K. D. M.; Travers, G.; Skelton, B. W.; Massi, M.; Payne, A. D.; Brown, D. H. Aust. J. Chem. 2012, 65, 823-833 10.1071/CH12044
68. Liu, A.; Zhang, X.; Chen, W. Organometallics 2009, 28, 4868-4871 10.1021/om900419b
69. Zhang, C.; Wang, Z.-X. Organometallics 2009, 28, 6507-6514 10.1021/om9006399
70. Berding, J.; van Dijkman, T. F.; Lutz, M.; Spek, A. L.; Bouwman, E. Dalton Trans. 2009, 6948-6955 10.1039/b905036a
71. Li, F.; Hu, J. J.; Koh, L. L.; Hor, T. S. A. Dalton Trans. 2010, 39, 5231-5241 10.1039/c000722f
72. Zhou, Y.; Xi, Z.; Chen, W.; Wang, D. Organometallics 2008, 27, 5911-5920 10.1021/om800711g
73. Guo, J.; Lv, L.; Wang, X.; Cao, C.; Pang, G.; Shi, Y. Inorg. Chem. Commun. 2013, 31, 74-78 10.1016/j.inoche.2013.03.011
74. Berding, J.; Lutz, M.; Spek, A. L.; Bouwman, E. Organometallics 2009, 28, 1845-1854 10.1021/om8010596
75. Huynh, H. V.; Jothibasu, R. Eur. J. Inorg. Chem. 2009, 1926-1931 10.1002/ejic.200801149
76. Soulé, J.-F.; Miyamura, H.; Kobayashi, S. J. Am. Chem. Soc. 2013, 135, 10602-10605 10.1021/ja404006w
77. Miyaura, N.; Suzuki, A. J. Chem. Soc., Chem. Commun. 1979, 866-867 10.1039/c39790000866
78. Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Lett. 1979, 20, 3437-3440 10.1016/S0040-4039(01)95429-2
79. Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176-4211 10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO;2-U
80. nd ed.; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004; pp 41-124.
81. Suzuki, A. Angew. Chem., Int. Ed. 2011, 50, 6722-6737 10.1002/anie.201101379
82. Han, F.-S. Chem. Soc. Rev. 2013, 42, 5270-5298 10.1039/c3cs35521g
83. Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. J. Am. Chem. Soc. 1985, 107, 972-980 10.1021/ja00290a037
84. Percec, V.; Bae, J.-Y.; Hill, D. H. J. Org. Chem. 1995, 60, 1060-1065 10.1021/jo00109a044
85. For an elegant study which confirms the benefic substitution of the halide or pseudo-halide by the base on the transmetalation rate, but also demonstrates two additional roles of hydroxide ions, when used as a base in the context of a palladium-catalyzed SM coupling, see: Amatore, C.; Jutand, A.; Le Duc, G. Chem.-Eur. J. 2011, 17, 2492-2503 10.1002/chem.201001911
86. Blakey, S. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 6046-6047 10.1021/ja034908b
87. Liu, J.; Robins, M. J. Org. Lett. 2004, 6, 3421-3423 10.1021/ol048490d
88. Liu, J.; Robins, M. J. Org. Lett. 2005, 7, 1149-1151 10.1021/ol050063s
89. Harris, M. R.; Hanna, L. E.; Greene, M. A.; Moore, C. E.; Jarvo, E. R. J. Am. Chem. Soc. 2013, 135, 3303-3306 10.1021/ja311783k
90. Zhong, C.; Sasaki, T.; Tada, M.; Iwasawa, Y. J. Catal. 2006, 242, 357-364 10.1016/j.jcat.2006.06.020
91. McGuinness, D. S.; Cavell, K. J.; Skelton, B. W.; White, A. H. Organometallics 1999, 18, 1596-1605 10.1021/om9809771
92. Bernhammer, J. C.; Huynh, H. V. Organometallics 2014, 33, 5845-5851 10.1021/om500484q
93. Ritleng, V.; Oertel, A. M.; Chetcuti, M. J. Dalton Trans. 2010, 39, 8153-8160 10.1039/c0dt00021c
94. Buchowicz, W.; Banach, A.; Conder, J.; Guńka, P. A.; Kubicki, D.; Buchalski, P. Dalton Trans. 2014, 43, 5847-5857 10.1039/c3dt53352b
95. Oertel, A. M.; Ritleng, V.; Chetcuti, M. J. Organometallics 2012, 31, 2829-2840 10.1021/om201101g
96. Oertel, A. M.; Ritleng, V.; Burr, L.; Chetcuti, M. J. Organometallics 2011, 30, 6685-6691 10.1021/om200864z
97. Wei, Y.; Petronilho, A.; Mueller-Bunz, H.; Albrecht, M. Organometallics 2014, 33, 5834-5844 10.1021/om500593s
98. Wu, J.; Nova, A.; Balcells, D.; Brudvig, G. W.; Dai, W.; Guard, L. M.; Hazari, N.; Lin, P.-H.; Pokhrel, R.; Takase, M. K. Chem.-Eur. J. 2014, 20, 5327-5337 10.1002/chem.201305021
99. Schaub, T.; Backes, M.; Radius, U. J. Am. Chem. Soc. 2006, 128, 15964-15965 10.1021/ja064068b
100. Zell, T.; Feierabend, M.; Halfter, B.; Radius, U. J. Organomet. Chem. 2011, 696, 1380-1387 10.1016/j.jorganchem.2011.01.003
101. Schaub, T.; Fischer, P.; Steffen, A.; Braun, T.; Radius, U.; Mix, A. J. Am. Chem. Soc. 2008, 130, 9304-9317 10.1021/ja074640e
102. Chiu, P. L.; Lai, C.-L.; Chang, C.-F.; Hu, C.-H.; Lee, H. M. Organometallics 2005, 24, 6169-6178 10.1021/om050224w
103. Xi, Z.; Zhang, X.; Chen, W.; Fu, S.; Wang, D. Organometallics 2007, 26, 6636-6642 10.1021/om700796g
104. Inamoto, K.; Kuroda, J.-i.; Hiroya, K.; Noda, Y.; Watanabe, M.; Sakamoto, T. Organometallics 2006, 25, 3095-3098 10.1021/om060043+
105. Inamoto, K.; Kuroda, J.-i; Kwon, E.; Hiroya, K.; Doi, T. J. Organomet. Chem. 2009, 694, 389-396 10.1016/j.jorganchem.2008.11.003
106. Kuroda, J.-i.; Inamoto, K.; Hiroya, K.; Doi, T. Eur. J. Org. Chem. 2009, 2251-2261 10.1002/ejoc.200900067
107. Tu, T.; Mao, H.; Herbert, C.; Xu, M.; Dötz, K. H. Chem. Commun. 2010, 46, 7796-7798 10.1039/c0cc03107k
108. Xu, M.; Li, X.; Sun, Z.; Tu, T. Chem. Commun. 2013, 49, 11539-11541 10.1039/c3cc46663a
109. Lee, C.-C.; Ke, W.-C.; Chan, K.-T.; Lai, C.-L.; Hu, C.-H.; Lee, H. M. Chem.-Eur. J. 2007, 13, 582-591 10.1002/chem.200600502
110. Liao, C.-Y.; Chan, K.-T.; Chang, Y.-C.; Chen, C.-Y.; Tu, C.-Y.; Hu, C.-H.; Lee, H. M. Organometallics 2007, 26, 5826-5833 10.1021/om700607m
111. Paulose, T. A. P.; Wu, S.-C.; Olson, J. A.; Chau, T.; Theaker, N.; Hassler, M.; Quail, J. W.; Foley, S. R. Dalton Trans. 2012, 41, 251-260 10.1039/c1dt10858a
112. Arvela, R. K.; Leadbeater, N. E.; Sangi, M. S.; Williams, V. A.; Granados, P.; Singer, R. D. J. Org. Chem. 2005, 70, 161-168 10.1021/jo048531j
113. Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581-581 10.1246/bcsj.44.581
114. Heck, R. F.; Nolley, J. P. J. Org. Chem. 1972, 37, 2320-2322 10.1021/jo00979a024
115. nd ed.; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004; pp 217-316.
116. The Mizoroki-Heck Reaction; Oestreich, M., Eds.; Wiley-VCH: Chichester, 2009.
117. Oestreich, M. Angew. Chem., Int. Ed. 2014, 53, 2282-2285 10.1002/anie.201310585
118. Inamoto, K.; Kuroda, J.-i.; Danjo, T.; Sakamoto, T. Synlett 2005, 1624-1626 10.1055/s-2005-869854
119. King, A. O.; Okukado, N.; Negishi, E.-i. J. Chem. Soc., Chem. Commun. 1977, 683-684 10.1039/c39770000683
120. nd ed.; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004; pp 619-670.
121. nd ed.; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004; pp 619-670.
122. Negishi, E.-i. Angew. Chem., Int. Ed. 2011, 50, 6738-6794 10.1002/anie.201101380
123. Xi, Z.; Zhou, Y.; Chen, W. J. Org. Chem. 2008, 73, 8497-8501 10.1021/jo8018686
124. Ullmann, F.; Bielecki, J. Ber. Dtsch. Chem. Ges. 1901, 34, 2174-2185 10.1002/cber.190103402141
125. Nelson, T. D.; Crouch, R. D. Cu, Ni, and Pd mediated homocoupling reactions in biaryl syntheses: The Ullmann reaction. In Organic Reactions; John Wiley & Sons: New York, 2004; Vol. 63, pp 265-555.
126. Huynh, H. V.; Wong, L. R.; Ng, P. S. Organometallics 2008, 27, 2231-2237 10.1021/om800004j
127. Ding, N.; Zhang, J.; Hor, T. S. A. Dalton Trans. 2009, 1853-1858 10.1039/b815876b
128. Mondal, K. C.; Samuel, P. P.; Li, Y.; Roesky, H. W.; Roy, S.; Ackermann, L.; Sidhu, N. S.; Sheldrick, G. M.; Carl, E.; Demeshko, S.; De, S.; Parameswaran, P.; Ungur, L.; Chibotaru, L. F.; Andrada, D. M. Eur. J. Inorg. Chem. 2014, 818-823 10.1002/ejic.201301598
129. Leleu, A.; Fort, Y.; Schneider, R. Adv. Synth. Catal. 2006, 348, 1086-1092 10.1002/adsc.200505409
130. Manolikakes, G.; Dastbaravardeh, N.; Knochel, P. Synlett 2007, 2077-2080 10.1055/s-2007-984906
131. Wenkert, E.; Ferreira, T. W.; Michelotti, E. L. J. Chem. Soc., Chem. Commun. 1979, 637-638 10.1039/c39790000637
132. Takei, H.; Miura, M.; Sugimura, H.; Okamura, H. Chem. Lett. 1979, 8, 1447-1450 10.1246/cl.1979.1447
133. Hintermann, L.; Schmitz, M.; Chen, Y. Adv. Synth. Catal. 2010, 352, 2411-2415 10.1002/adsc.201000350
134. Cornella, J.; Martin, R. Org. Lett. 2013, 15, 6298-6301 10.1021/ol4031815
135. Ishizuka, K.; Seike, H.; Hatakeyama, T.; Nakamura, M. J. Am. Chem. Soc. 2010, 132, 13117-13119 10.1021/ja104155f
136. Normand, A. T.; Yen, S. K.; Huynh, H. V.; Hor, T. S. A.; Cavell, K. J. Organometallics 2008, 27, 3153-3160 10.1021/om800140n
137. Normand, A. T.; Hawkes, K. J.; Clement, N. D.; Cavell, K. J.; Yates, B. F. Organometallics 2007, 26, 5352-5363 10.1021/om070181e
138. McGuinness, D. S.; Cavell, K. J.; Yates, B. F.; Skelton, B. W.; White, A. H. J. Am. Chem. Soc. 2001, 123, 8317-8328 10.1021/ja010628p
139. Nakao, Y.; Kashihara, N.; Kanyiva, K. S.; Hiyama, T. Angew. Chem., Int. Ed. 2010, 49, 4451-4454 10.1002/anie.201001470
140. Shih, W.-C.; Chen, W.-C.; Lai, Y.-C.; Yu, M.-S.; Ho, J.-J.; Yap, G. P. A.; Ong, T.-G. Org. Lett. 2012, 14, 2046-2049 10.1021/ol300570f
141. Lee, W.-C.; Wang, C.-H.; Lin, Y.-H.; Shih, W.-C.; Ong, T.-G. Org. Lett. 2013, 15, 5358-5361 10.1021/ol402644y
142. Nakao, Y.; Yamada, Y.; Kashihara, N.; Hiyama, T. J. Am. Chem. Soc. 2010, 132, 13666-13668 10.1021/ja106514b
143. Tamura, R.; Yamada, Y.; Nakao, Y.; Hiyama, T. Angew. Chem., Int. Ed. 2012, 51, 5679-5682 10.1002/anie.201200922
144. See also: Nakao, Y.; Idei, H.; Kanyiva, K. S.; Hiyama, T. J. Am. Chem. Soc. 2009, 131, 15996-15997 10.1021/ja907214t
145. Tsai, C.-C.; Shih, W.-C.; Fang, C.-H.; Li, C.-Y.; Ong, T.-G.; Yap, G. P. A. J. Am. Chem. Soc. 2010, 132, 11887-11889 10.1021/ja1061246
146. Miyazaki, Y.; Yamada, Y.; Nakao, Y.; Hiyama, T. Chem. Lett. 2012, 41, 298-300 10.1246/cl.2012.298
147. Hoshimoto, Y.; Hayashi, Y.; Suzuki, H.; Ohashi, M.; Ogoshi, S. Angew. Chem., Int. Ed. 2012, 51, 10812-10815 10.1002/anie.201206186
148. Ho, C.-Y.; He, L. Angew. Chem., Int. Ed. 2010, 49, 9182-9186 10.1002/anie.201001849
149. Ho, C.-Y.; Jamison, T. F. Angew. Chem., Int. Ed. 2007, 46, 782-785 10.1002/anie.200603907
150. Ho, C.-Y.; He, L. Chem. Commun. 2012, 48, 1481-1483 10.1039/c1cc14593b
151. Schleicher, K. D.; Jamison, T. F. Org. Lett. 2007, 9, 875-878 10.1021/ol063111x
152. Nakai, K.; Yoshida, Y.; Kurahashi, T.; Matsubara, S. J. Am. Chem. Soc. 2014, 136, 7797-7800 10.1021/ja500666h
153. Matsubara, K.; Ueno, K.; Koga, Y.; Hara, K. J. Org. Chem. 2007, 72, 5069-5076 10.1021/jo070313d
154. Henrion, M.; Chetcuti, M. J.; Ritleng, V. Chem. Commun. 2014, 50, 4624-4627 10.1039/c4cc00959b
155. See also: Oertel, A. M.; Ritleng, V.; Busiah, A.; Veiros, L. F.; Chetcuti, M. J. Organometallics 2011, 30, 6495-6498 10.1021/om200819c
156. Ray, S.; Shaikh, M. M.; Ghosh, P. Eur. J. Inorg. Chem. 2009, 1932-1941 10.1002/ejic.200801060
157. Samantaray, M. K.; Shaikh, M. M.; Ghosh, P. Organometallics 2009, 28, 2267-2275 10.1021/om801186f
158. Kumar, S.; Narayanan, A.; Rao, M. N.; Shaikh, M. M.; Ghosh, P. J. Organomet. Chem. 2012, 696, 4159-4165 10.1016/j.jorganchem.2011.09.007
159. Huang, G.; Sun, H.; Qiu, X.; Shen, Y.; Jiang, J.; Wang, L. J. Organomet. Chem. 2011, 696, 2949-2957 10.1016/j.jorganchem.2011.04.039
160. Berini, C.; Brayton, D. F.; Mocka, C.; Navarro, O. Org. Lett. 2009, 11, 4244-4247 10.1021/ol901825u
161. Bouffard, J.; Itami, K. Org. Lett. 2009, 11, 4410-4413 10.1021/ol9017613
162. Maekawa, T.; Sekizawa, H.; Itami, K. Angew. Chem., Int. Ed. 2011, 50, 7022-7026 10.1002/anie.201102092
163. Berini, C.; Navarro, O. Chem. Commun. 2012, 48, 1538-1540 10.1039/c1cc10826c
164. Schaub, T.; Radius, U. Chem.-Eur. J. 2005, 11, 5024-5030 10.1002/chem.200500231
165. Schaub, T.; Backes, M.; Radius, U. Organometallics 2006, 25, 4196-4206 10.1021/om0604223