Abstract
This chapter describes applications of N-heterocyclic carbenes (NHCs) in oxidation chemistry. The strong σ-donation capabilities of the NHCs allow an efficient stabilisation of metal centres in high oxidation states, while high metal-NHC bond dissociation energies suppress their oxidative decomposition. These properties make NHCs ideal ligands for oxidation processes. The first part of this chapter is dedicated to the reactivity of NHC-metal complexes towards molecular oxygen whilst the second half highlights all oxidation reactions catalysed by such complexes. These include oxidation of alcohols and olefins, oxidative cyclisations, hydrations of alkynes and nitriles, oxidative cleavage of alkenes and the oxidation of methane.
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References
Rogers MM, Stahl SS (2007) In: Glorius F (ed) N-Heterocyclic carbenes in transition metal catalysis. Springer, Berlin/Heidelberg. Top Organomet Chem 21:21–46
Strassner T (2007) In: Meyer F, Limberg C (eds) Organometallic oxidation catalysis. Springer, Berlin/Heidelberg. Top Organomet Chem 22:125–148
Schultz MJ, Sigman MS (2006) In: Nolan SP (ed) N-Heterocyclic carbenes in synthesis. Wiley-VCH, Weinheim, pp 103–118
Popp BV, Stahl SS (2007) In: Meyer F, Limberg C (eds) Organometallic oxidation catalysis. Springer, Berlin/Heidelberg. Top Organomet Chem 22:149–189
Konnick MM, Guzei IA, Stahl SS (2004) J Am Chem Soc 126:10212–10213
Stahl SS (2004) Angew Chem Int Ed 43:3400–3420
Konnick MM, Gandhi BA, Guzei IA, Stahl SS (2006) Angew Chem Int Ed 45:2904–2907
Popp BV, Stahl SS (2007) J Am Chem Soc 129:4410–4422
Konnick MM, Stahl SS (2008) J Am Chem Soc 130:5753–5762
Yamashita M, Goto K, Kawashima T (2005) J Am Chem Soc 127:7294–7295
Popp BV, Wendlandt JE, Landis CR, Stahl SS (2007) Angew Chem Int Ed 46:601–604
Häller LJL, Mas-Marza E, Moreno A, Lowe JP, Macgregor SA, Mahon MF, Pregosin PS, Whittlesey MK (2009) J Am Chem Soc 131:9618–9619
Hu X, Castro-Rodriguez I, Meyer K (2004) J Am Chem Soc 126:13464–13473
Dibble BR, Sigman MS (2006) Inorg Chem 45:8430–8441
Dibble BR, Sigman MS (2003) J Am Chem Soc 125:872–873
Larock RC (1999) Comprehensive organic transformations, 2nd ed. VCH, New York, pp 1234–1250
Muzart J (2003) Tetrahedron 59:5789–5816
Nishimura T, Onoue T, Ohe K, Uemura S (1999) J Org Chem 64:6750–6755
Nishimura T, Maeda Y, Kakiuchi N, Uemura S (2000) J Chem Soc Perkin Trans 1:1915–1918
Nishimura T, Kakiuchi N, Onoue T, Ohe K, Uemura S (2000) J Chem Soc Perkin Trans 1:4301–4305
Ten Brink GJ, Arends IWCE, Sheldon RA (2000) Science 287:1636–1639
Jensen DR, Schultz MJ, Mueller JA, Sigman MS (2003) Angew Chem Int Ed 42:3810–3813
Mueller JA, Goller CP, Sigman MS (2004) J Am Chem Soc 126:9724–9734
Schultz MJ, Hamilton SS, Jensen DR, Sigman MS (2005) J Org Chem 70:3343–3352
Jensen DR, Sigman MS (2003) Org Lett 5:63–65
Chen T, Jiang JJ, Xu Q, Shi M (2007) Org Lett 9:865–868
Liu L, Wang F, Shi M (2009) Organometallics 28:4416–4420
Liu SJ, Liu L, Shi M (2009) Appl Organomet Chem 23:183–190
Guram AS, Bei X, Turner HW (2003) Org Lett 5:2485–2487
Bei X, Hagemeyer A, Volpe A, Saxton R, Turner H, Guram AS (2004) J Org Chem 69:8626–8633
Brayton DF, Mocka C, Berini C, Navarro O (2009) Org Lett 11:4244–4247
Navarro O, Kaur H, Mahjoor P, Nolan SP (2004) J Org Chem 69:3173–3180
Hanasaka F, Fujita K-I, Yamaguchi R (2004) Organometallics 23:1490–1492
Hanasaka F, Fujita K-I, Yamaguchi R (2005) Organometallics 24:3422–3433
Edwards MG, Jazzar RFR, Paine BM, Shermer DJ, Whittlesey MK, Williams JMJ, Edney DD (2004) Chem Commun 90–91
Burling S, Whittlesey MK, Williams JMJ (2005) Adv Synth Catal 347:591–594
Hintermann L, Labonne A (2007) Synthesis 1121–1150
Marion N, Ramon RS, Nolan SP (2009) J Am Chem Soc 131:448–449
Ramon SR, Marion N, Nolan SP (2009) Chem Eur J 15:8695–8697
Smidt J, Hafner W, Jira R, Sedlmeier J, Sieber R, Rüttinger R, Kojer H (1959) Angew Chem 71:176–182
Cornell CN, Sigman MS (2005) J Am Chem Soc 127:2796–2797
Rogers MM, Wendledt JE, Guzei IA, Stahl SS (2006) Org Lett 8:2257–2260
Scarborough CC, Bergant A, Sazama GT, Guzei IA, Spencer LC, Stahl SS (2009) Tetrahedron 65:5084–5092
Poyatos M, Mata JA, Falomir E, Crabtree RH, Peris E (2003) Organometallics 22:1110–1114
Muehlhofer M, Strassner T, Herrmann WA (2002) Angew Chem Int Ed 41:1745–1747
Meyer D, Taige MA, Zeller A, Hohlfeld K, Ahrens S, Strassner T (2009) Organometallics 28:2142–2149
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Jurčík, V., Cazin, C.S.J. (2010). N-Heterocyclic Carbene Complexes in Oxidation Reactions. In: Cazin, C. (eds) N-Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis. Catalysis by Metal Complexes, vol 32. Springer, Dordrecht. https://doi.org/10.1007/978-90-481-2866-2_10
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DOI: https://doi.org/10.1007/978-90-481-2866-2_10
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