Abstract
This chapter surveys computational studies on heteroatom-assisted C–H activation at group 8 and 9 metal centres and will cover the literature since 2009. The chapter first considers work where the mechanism of the C–H activation step is the primary concern and categorizes these into intramolecular (with directing groups) and intermolecular processes. Studies on C–H activation and functionalization will be presented, classified in terms of the nature of the functionalization process (oxidative coupling to form heterocycles, alkenylation and amination).
Keywords
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsNotes
- 1.
High-level wave function methods promise the accurate treatment of these long-range electron correlation effects; however, such methods are still too computationally demanding for routine use on large model systems.
References
Balcells D, Clot E, Eisenstein O (2010) Chem Rev 110:749–823
Boutadla Y, Davies DL, Macgregor SA, Poblador-Bahamonde AI (2009) Dalton Trans 14(30):5820–5831
Perutz RN, Sabo-Etienne S (2007) Angew Chem Int Ed 46:2578–2592
Vastine BA, Hall MB (2009) Coord Chem Rev 253:1202–1218
Lapointe D, Fagnou K (2010) Chem Lett 39:1119–1126
Biswas B, Sugimoto M, Sakaki S (2000) Organometallics 19:3895–3908
Davies DL, Donald SMA, Macgregor SA (2005) J Am Chem Soc 127:13754–13755
Webb JR, Burgess SA, Cundari TR, Gunnoe TB (2013) Dalton Trans 42:16646–16665
Guan W, Sayyed FB, Zeng G, Sakaki S (2014) Inorg Chem 53:6444–6457
Grimme S, Antony J, Ehrlich S, Krieg H (2010) J Chem Phys 132:154104
Grimme S (2006) J Comput Chem 27:1787–1799
Chai J-D, Head-Gordon M (2008) Phys Chem Chem Phys 10:6615–6620
Zhao Y, Truhlar D (2008) Theor Chem Acc 120:215–241
Minenkov Y, Occhipinti G, Jensen VR (2009) J Phys Chem A 113:11833–11844
Carr KJT, Davies DL, Macgregor SA, Singh K, Villa-Marcos B (2014) Chem Sci 5:2340–2346
Li J, Hu W, Peng Y, Zhang Y, Li J, Zheng W (2014) Organometallics 33:2150–2159
Li L, Brennessel WW, Jones WD (2009) Organometallics 28:3492–3500
Clot E, Eisenstein O, Jasim N, Macgregor SA, McGrady JE, Perutz RN (2011) Acc Chem Res 44:333–348
Ikemoto H, Yoshino T, Sakata K, Matsunaga S, Kanai M (2014) J Am Chem Soc 136:5424–5431
Cannon JS, Zou L, Liu P, Lan Y, O’Leary DJ, Houk KN, Grubbs RH (2014) J Am Chem Soc 136:6733–6743
Haller LJL, Page MJ, Macgregor SA, Mahon MF, Whittlesey MK (2009) J Am Chem Soc 131:4604–4605
Krueger A, Haeller LJL, Mueller-Bunz H, Serada O, Neels A, Macgregor SA, Albrecht M (2011) Dalton Trans 40:9911–9920
Meier SK, Young KJH, Ess DH, Tenn WJ III, Oxgaard J, Goddard WA III, Periana RA (2009) Organometallics 28:5293–5304
Bischof SM, Ess DH, Meier SK, Oxgaard J, Nielsen RJ, Bhalla G, Goddard WA III, Periana RA (2010) Organometallics 29:742–756
Webster-Gardiner MS, Fu R, Fortman GC, Nielsen RJ, Gunnoe TB, Goddard WA III (2015) Catal Sci Technol 5:96–100
Cross WB, Razak S, Singh K, Warner AJ (2014) Chem Eur J 20:13203–13209
Davies DL, Donald SMA, Al-Duaij O, Fawcett J, Little C, Macgregor SA (2006) Organometallics 25:5976–5978
Rhinehart JL, Manbeck KA, Buzak SK, Lippa GM, Brennessel WW, Goldberg KI, Jones WD (2012) Organometallics 31:1943–1952
Fu R, Nielsen RJ, Goddard WA III, Fortman GC, Gunnoe TB (2014) ACS Catal 4:4455–4465
Fu R, O’Reilly ME, Nielsen RJ, Goddard WA III, Gunnoe TB (2015) Chem Eur J 21:1286–1293
O’Reilly ME, Fu R, Nielsen RJ, Sabat M, Goddard WA III, Gunnoe TB (2014) J Am Chem Soc 136:14690–14693
Guimond N, Gorelsky SI, Fagnou K (2011) J Am Chem Soc 133:6449–6457
Xu L, Zhu Q, Huang G, Cheng B, Xia Y (2012) J Org Chem 77:3017–3024
Wodrich MD, Ye B, Gonthier JF, Corminboeuf C, Cramer N (2014) Chem Eur J 20:15409–15418
Wu S, Zeng R, Fu C, Yu Y, Zhang X, Ma S (2015) Chem Sci 6:2275–2285
Xing Z, Huang F, Sun C, Zhao X, Liu J, Chen D (2015) Inorg Chem 54:3958–3969
Yu S, Liu S, Lan Y, Wan B, Li X (2015) J Am Chem Soc 137:1623–1631
Chen W-J, Lin Z (2015) Organometallics 34:309–318
Zhao D, Shi Z, Glorius F (2013) Angew Chem Int Ed 52:12426–12429
Simmons EM, Hartwig JF (2012) Angew Chem Int Ed 51(13):3066–3072
Algarra AG, Cross WB, Davies DL, Khamker Q, Macgregor SA, McMullin CL, Singh KJ (2014) Org Chem 79:1954–1970
Ruiz S, Villuendas P, Ortuño MA, Lledós A, Urriolabeitia EP (2015) Chem Eur J 21:8626–8636
Frasco DA, Lilly CP, Boyle PD, Ison EA (2013) ACS Catal 3:2421–2429
Liu L, Wu Y, Wang T, Gao X, Zhu J, Zhao Y (2014) J Org Chem 79:5074–5081
Davies DL, Donald SMA, Al-Duaij O, Macgregor SA, Polleth M (2006) J Am Chem Soc 128:4210–4211
Kozuch S, Shaik S (2011) Acc Chem Res 44:101–110
Park Y, Seo J, Park S, Yoo EJ, Lee PH (2013) Chem Eur J 19:16461–16468
Seo J, Park Y, Jeon I, Ryu T, Park S, Lee PH (2013) Org Lett 15:3358–3361
Zhang Q, Yu H-Z, Li Y-T, Liu L, Huang Y, Fu Y (2013) Dalton Trans 42:4175–4184
Gong T-J, Xiao B, Liu Z-J, Wan J, Xu J, Luo D-F, Fu Y, Liu L (2011) Org Lett 13:3235–3237
Algarra AG, Davies DL, Khamker Q, Macgregor SA, McMullin CL, Singh K, Villa-Marcos B (2015) Chem Eur J 21:3087–3096
Wu J-Q, Qiu Z-P, Zhang S-S, Liu J-G, Lao Y-X, Gu L-Q, Huang Z-S, Li J, Wang H (2015) Chem Commun 51:77–80
Figg TM, Park S, Park J, Chang S, Musaev DG (2014) Organometallics 33:4076–4085
Acknowledgements
We thank Prof. Dai Davies (University of Leicester) and his group for many fruitful discussions, the EPSRC for financial support through awards EP/J002712/1 (KJTC) and EP/J021911/1 (CLM) and the Université de Lille I, Science et Technologies, for a visiting professorship during which much of this chapter was written.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2015 Springer International Publishing Switzerland
About this chapter
Cite this chapter
Carr, K.J.T., Macgregor, S.A., McMullin, C.L. (2015). Computational Studies on Heteroatom-Assisted C–H Activation and Functionalisation at Group 8 and 9 Metal Centres. In: Dixneuf, P., Doucet, H. (eds) C-H Bond Activation and Catalytic Functionalization I. Topics in Organometallic Chemistry, vol 55. Springer, Cham. https://doi.org/10.1007/3418_2015_125
Download citation
DOI: https://doi.org/10.1007/3418_2015_125
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-24628-4
Online ISBN: 978-3-319-24630-7
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)