Abstract
Organometallic compounds have been found to be of use in cleaving C–C bonds, as strong metal–carbon bonds can be formed to replace the bond that is broken. Studies of the mechanism of C–C cleavage can provide insight into how these bonds can be cleaved, and can give valuable information that can be used to develop new strategies for breaking C–C bonds and using the products in catalysis. In this chapter, we will examine a number of systems where mechanistic information has been obtained in C–C cleavage.
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Jones WD (1993) Nature 364:676
Perthuisot C, Edelbach BL, Zubris DL, Simhai N, Iverson CN, Müller C, Satoh T, Jones WD (2002) J Mol Catal A Chem 189:157
Luo Y-R (2007) Comprehensive handbook of bond energies. CRC, Boca Raton
Simões JAM (1990) Beauchamp. Chem Rev 90:629
Atkinson ER, Levins PL, Dickelman TE (1964) Chem Ind (Lond) 934
Eisch JJ, Piotrowski AM, Han KI, Krüger C, Tsay YH (1985) Organometallics 4:224
Schwager H, Spyroudis S, Vollhardt KPC (1990) J Organomet Chem 382:191
Lu Z, Jun C-H, de Gala SR, Sigalas M, Eisenstein O, Crabtree RHJ (1993) Chem Soc Chem Commun 1877
Jones WD, Feher FJ (1989) Acc Chem Res 22:91
Perthuisot C, Jones WD (1994) J Am Chem Soc 116:3647
Chin RM, Dong L, Duckett SB, Jones WD (1992) Organometallics 11:871
Wick DD, Jones WD (2009) Inorg Chim Acta 362:4416
Perthuisot C, Edelbach BL, Zubris DL, Jones WD (1997) Organometallics 16:2016
Edelbach BL, Lachicotte RJ, Jones WD (1998) J Am Chem Soc 120:2843
Edelbach BE, Vicic DA, Lachicotte RJ, Jones WD (1998) Organometallics 17:4784
Simhai N, Iverson CN, Edelbach BE, Jones WD (2001) Organometallics 20:2759
Hirschler MM, Taylor RJ (1980) Chem Soc Chem Commun 967
Edelbach BL, Lachicotte RJ, Jones WD (1999) Organometallics 18:4040
Müller C, Lachicotte RJ, Jones WD (2002) Organometallics 21:1975
Edelbach BL, Lachicotte RJ, Jones WD (1999) Organometallics 18:4660
Satoh T, Jones WD (2001) Organometallics 20:2916
Iverson CN, Jones WD (2001) Organometallics 20:5745
Abba M, Yamamoto T (1997) J Organomet Chem 532:267
Favero G, Movillo A, Turco A (1983) J Organomet Chem 241:251
Morvillo A, Turco A (1981) J Organomet Chem 208:103
Parshall GW (1974) J Am Chem Soc 96:2360
Churchill D, Shin JH, Hascall T, Hahn JM, Bridgewater BM, Parkin G (1999) Organometallics 18:2403
Gerlach DH, Kane AR, Parshall GW, Jesson JP, Muetterties EL (1971) J Am Chem Soc 93:3543
Burmeister JL, Edwards LM (1971) J Chem Soc A 1663
Favero G, Gaddi M, Morvillo A, Turco A (1978) J Organomet Chem 149:395
Cassar L (1973) J Organomet Chem 54:C57
Tsuji Y, Kusui T, Kojima T, Sugiura Y, Yamada N, Tanaka S, Ebihara M, Kawamura T (1998) Organometallics 17:4835
Luo F-H, Chu C-I, Cheng C-H (1998) Organometallics 17:1025
Huang J, Haar CM, Nolan SP, Marcone JE, Moloy KG (1999) Organometallics 18:297
Marcone JE, Moloy KG (1998) J Am Chem Soc 120:8527
Garcia JJ, Jones WD (2000) Organometallics 19:5544
Garcia JJ, Brunkan NM, Jones WD (2002) J Am Chem Soc 124:9547
Garcia JJ, Arévalo A, Brunkan NM, Jones WD (2004) Organometallics 23:3997
Atesin TA, Li T, Lachaize S, Brennessel WW, Garcia JJ, Jones WD (2007) J Am Chem Soc 129:7562
Atesin TA, Li T, Lachaize S, Brennessel WW, Garcia JJ, Jones WD (2008) Organometallics 27:3811
Li T, Garcia JJ, Brennessel WW, Jones WD (2010) Organometallics 29:2430
Brauer DJ, Kruger C (1977) Inorg Chem 16:884
McKinney RJ, Roe DC (1985) J Am Chem Soc 107:261
Tolman CA, Kinney RJ, Seidel WC, Druliner JD, Stevens WR (1985) Adv Catal 33:1
Tolman CA, Seidel WC, Druliner JD, Domaille PJ (1984) Organometallics 3:33
Bini L, Müller CM, Wilting J, von Chrzanowski L, Spek AL, Vogt D (2007) J Am Chem Soc 129:12622
Brunkan NM, Jones WD (2003) J Organomet Chem 683:77
Brunkan NM, Brestensky DM, Jones WD (2004) J Am Chem Soc 126:3627
Chaumonnot A, Lamy F, Sabo-Etienne S, Donnadieu B, Chaudret B, Barthelat JC, Galland JC (2004) Organometallics 23:3363
Wilting J, Müller C, Hewat AC, Ellis DD, Tooke DM, Spek AL, Vogt D (2005) Organometallics 24:13
Swartz BD, Reinartz NM, Garcia JJ, Jones WD (2008) J Am Chem Soc 130:8548
Acosta-Ramirez A, Flores-Gaspar A, Munoz-Hernandez M, Arevalo A, Jones WD, Garcia J (2007) J Organometallics 26:1712
Li T, Jones WD (2011) Organometallics 30:547
Acosta-Ramirez A, Munoz-Hernandez M, Jones WD, Garcia JJ (2006) J Organomet Chem 691:3895
Acosta-Ramirez A, Munoz-Hernandez M, Jones WD, Garcia J (2007) J Organometallics 26:5766
Acosta-Ramirez A, Flores-Alamo M, Jones WD, Garcia J (2008) J Organometallics 27:1834
Acosta-Ramirez A, Morelas-Morelas D, Serrano-Becerra JM, Arevalo A, Jones WD, Garcia JJ (2008) J Mol Catal A Chem 288:14
Grochowski MR, Morris J, Brennessel WW, Jones WD (2011) Organometallics 30:5604
Fryzuk MD, Piers WE, Rettig S (1992) J Can J Chem 70:2381
Müller C, Lachicotte RJ, Jones WD (2001) J Am Chem Soc 123:9718
Gunay A, Jones WD (2007) J Am Chem Soc 129:8729
Gunay A, Müller C, Lachicotte RJ, Brennessel WW, Jones WD (2009) Organometallics 28:6524
Gozin M, Weisman A, Ben-David Y, Milstein D (1993) Nature 364:699
Liou S-Y, Gozin M, Milstein D (1995) J Am Chem Soc 117:9774
Rybtchinski B, Vigalok A, Ben-David Y, Milstein D (1996) J Am Chem Soc 118:12406
Rybtchinski B, Milstein D (1999) Angew Chem Int Ed 38:870
Subtraction of the statistical part of the free energy, RT ln (k 1/k 2), would only be appropriate in comparing the enthalpy of reaction
van der Boom ME, Kraatz H-B, Ben-David Y, Milstein S (1996) Chem Commun 2167
Liou S-Y, van der Boom ME, Milstein D (1998) Chem Commun 687
Gandelman M, Vigalok A, Shimon LJW, Milstein D (1997) Organometallics 16:3981
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Jones, W.D. (2013). Mechanistic Studies of Transition Metal-Mediated C–C Bond Activation. In: Dong, G. (eds) C-C Bond Activation. Topics in Current Chemistry, vol 346. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2013_491
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DOI: https://doi.org/10.1007/128_2013_491
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