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For general references, see: (a) Collman, J. P.; Hegedus, L. S.; Norton. J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Sausalito, CA, 1987.
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7
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0000139820
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For a competitive alkyl-alkyl versus alkyl-carboxylate reductive elimination, see: (a) Canty, A. J.; Jin, H.; Skelton, B. W.; White, A. H. Inorg. Chem. 1998, 37, 3975.
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(b) Williams, B. S.; Holland, A. W.; Goldberg, K. I. J. Am. Chem. Soc. 1999, 121, 252.
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0242498414
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For a noncompetitive aryl-halide reductive elimination from a Pd(II) center, see: (a) Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 13944.
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12
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0002892941
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N2 mechanism was also proposed in the Shilov chemistry: Luinstra, G. A.; Wang, E.; Stahl. S. S.; Labinger, J. A.; Bercaw, J. E. J. Organomet. Chem. 1995, 504, 75.
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(a) Iodobenzene formation in a Pt(IV) system remains a sole example of an aryl-halide reductive elimination for nearly 40 years: Ettorre, R. Inorg. Nucl. Chem. Lett. 1969, 5, 45.
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Ettorre, R.1
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14
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2)-X bond formation in chelated systems, see: van Belzen, R.; Elsevier, C. J.; Dedieu, A.; Veldman, N.; Spek, A. E. Organometallics 2003, 22, 722.
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Spek, A.E.5
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0001203082
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(c) Alsters, P. L.; Engel, P. F.; Hogerheide, M. P.; Copijn, M.; Spek, A. E.; van Koten, G. Organometallics 1993, 12, 1831.
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Alsters, P.L.1
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(a) Yahav, A.; Goldberg, I.; Vigalok, A. J. Am. Chem. Soc. 2003, 125, 13634.
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(b) Yahav, A.; Goldberg, I.; Vigalok, A. Inorg. Chem. 2005, 44, 1547.
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(a) Ananikov, V. P.; Mitchenko, S. A.; Beletskaya, I. P. Russ. J. Org. Chem. (Engl. Transl.) 2002, 38, 636.
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(b) Ananikov, V. P.; Musaev, D. G.; Morokuma, K. Organometallics 2001, 20, 1652.
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(d) Ananikov, V. P.; Musaev, D. G.; Morokuma, K. Organometallics 2005, 24, 715.
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Organometallics
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Ananikov, V.P.1
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Morokuma, K.3
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23
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33745933414
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note
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In some cases, small amounts of highly unstable Pt(IV) diiodo complexes with bulkier ligands were observed at -70 °C. At higher temperatures, these complexes underwent rapid C-1 reductive elimination.
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24
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33644945352
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Yahav, A.; Goldberg, I.; Vigalok, A. Organometallics 2005, 24, 5654.
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Organometallics
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Yahav, A.1
Goldberg, I.2
Vigalok, A.3
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25
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9644281424
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Maitlis, P. M.; Haynes, A.; James, B. R.; Catellani, M.; Chiusoli, G. P. Dalton Trans. 2004, 3409.
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Dalton Trans.
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Maitlis, P.M.1
Haynes, A.2
James, B.R.3
Catellani, M.4
Chiusoli, G.P.5
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26
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33745940837
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note
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See Supporting Information for full experimental details.
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29
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2342433098
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(c) Makino, T.; Yamamoto, Y.; Itoh, K. Organometallics 2004, 23, 1730.
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Organometallics
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Makino, T.1
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Itoh, K.3
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30
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0000886342
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(d) Kohara, T.; Yamomoto, T.; Yamamoto, A. J. Organomet. Chem. 1980, 192, 265.
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Kohara, T.1
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31
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0034249672
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(e) For a review, see: van Leeuwen, P. W. N. M.; Kamen P. C. J.; Reek, J. N. H.; Dierkes, P. Chem. Rev. 2000, 100, 2741.
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Chem. Rev.
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Van Leeuwen, P.W.N.M.1
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Reek, J.N.H.3
Dierkes, P.4
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(a) Casey, C. P.; Whiteker, G. T.; Melville, M. G.; Petrovich, L. M.; Gavney, J. A., Jr.; Powell, D. R. J. Am. Chem. Soc. 1992, 114, 5535.
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Casey, C.P.1
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Petrovich, L.M.4
Gavney Jr., J.A.5
Powell, D.R.6
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34
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33745954869
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note
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2 cannot be excluded.
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35
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33745947637
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note
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In the presence of TBA-Br, the biaryl formation from 6a,b might occur via the direct elimination or chelate ring-opening. Ion-pair rearrangement mechanisms also cannot be ruled out at this stage.
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