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Synlett 2016; 27(04): 477-485
DOI: 10.1055/s-0035-1560366
DOI: 10.1055/s-0035-1560366
synpacts
Activation of Small Molecules at N-Heterocyclic Carbene Centers
Further Information
Publication History
Received: 08 September 2015
Accepted after revision: 05 October 2015
Publication Date:
11 November 2015 (online)
Abstract
The transition-metal-like behavior of N-heterocyclic carbenes (NHCs) in the activation of small molecules such as CO, NO, N2O, H2, and NH3 is reviewed. The resemblance to transition metals is mainly attributed to the adjustable electronic properties of the carbene centers through modification of their structure. Furthermore, applications of NHCs in the activation of various C–H bonds for functionalization are explored.
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References
-
1a Hopkinson MN, Richter C, Schedler M, Glorius F. Nature 2014; 510: 485
- 1b Murphy LJ, Robertson KN, Masuda JD, Clyburne JA. C In N-Heterocyclic Carbenes: Effective Tools for Organometallic Synthesis . Nolan SP. Wiley-VCH; Weinheim: 2014: 427
- 2 Singh MS In Reactive Intermediates in Organic Chemistry: Structure, Mechanism, and Reactions. Wiley-VCH; Weinheim: 2014: 153
-
3 Arduengo AJ. III, Harlow RL, Kline M. J. Am. Chem. Soc. 1991; 113: 361
- 4 Martin D, Soleilhavoup M, Bertrand G. Chem. Sci. 2011; 2: 389
- 5 Yue HR, Ma XB, Gong JL. Acc. Chem. Res. 2014; 47: 1483
- 6 Lyashchuk SN, Skrypnik YG. Tetrahedron Lett. 1994; 35: 5271
- 7 Dixon DA, Arduengo AJ. III, Dobbs KD, Khasnis DV. Tetrahedron Lett. 1995; 36: 645
- 8 Denk MK, Rodezno JM, Gupta S, Lough AJ. J. Organomet. Chem. 2001; 617–618: 242
- 9a Lavallo V, Canac Y, Donnadieu B, Schoeller WW, Bertrand G. Angew. Chem. Int. Ed. 2006; 45: 3488
-
9b Hudnall TW, Bielawski CW. J. Am. Chem. Soc. 2009; 131: 16039
- 9c Siemeling U, Farber C, Bruhn C, Leibold M, Selent D, Baumann W, von Hopffgarten M, Goedeckec C, Frenking G. Chem. Sci. 2010; 1: 697
- 9d Martin D, Moore CE, Rheingold AL, Bertrand G. Angew. Chem. Int. Ed. 2013; 52: 7014
- 10 Goedecke C, Leibold M, Siemeling U, Frenking G. J. Am. Chem. Soc. 2011; 133: 3557
- 11 Li X, Liu K, Xu X, Ma L, Wang H, Jiang D, Zhang Q, Lu C. Chem. Commun. 2011; 47: 7860
- 12 Nitric Oxide Donors for Pharmaceutical and Biological Applications . Wang PG, Cai TB, Taniguchi N. Wiley-VCH; Weinheim: 2005
- 13 Park J, Song H, Kim Y, Eun B, Kim Y, Bae DY, Park S, Rhee YM, Kim WJ, Kim K, Lee E. J. Am. Chem. Soc. 2015; 137: 4642
- 14 Tskhovrebov AG, Solari E, Wodrich MD, Scopelliti R, Severin K. Angew. Chem. Int. Ed. 2012; 51: 232
- 15a Duong HA, Tekavec TN, Arif AM, Louie J. Chem. Commun. 2004; 112
- 15b Kuchenbeiser G, Soleilhavoup M, Donnadieu B, Bertrand G. Chem. Asian J. 2009; 4: 1745
-
15c Martin D, Lassauque N, Donnadieu B, Bertrand G. Angew. Chem. Int. Ed. 2012; 51: 6172
- 15d Gurau G, Rodríguez H, Kelley SP, Janiczek P, Kalb RS, Rogers RD. Angew. Chem. Int. Ed. 2011; 50: 12024
-
16a Zhou H, Zhang W.-Z, Liu C.-H, Qu J.-P, Lu X.-B. J. Org. Chem. 2008; 73: 8039
- 16b Kayaki Y, Yamamoto M, Ikariya T. Angew. Chem. Int. Ed. 2009; 48: 4194
- 16c Riduan SN, Zhang Y, Ying JY. Angew. Chem. Int. Ed. 2009; 48: 3322
- 17 Huang F, Lu G, Zhao L, Li H, Wang Z.-X. J. Am. Chem. Soc. 2010; 132: 12388
- 18 Riduan SN, Ying JY, Zhang Y. ChemCatChem 2013; 5: 1490
- 19 Jacquet O, Das Neves Gomes C, Ephritikhine M, Cantat T. J. Am. Chem. Soc. 2012; 134: 2934
- 20 Wang B, Cao Z. RSC Advances 2013; 3: 14007
- 21 Zhou Q, Li Y. J. Am. Chem. Soc. 2015; 137: 10182
- 22 Tomioka H In Reactive Intermediate Chemistry . Moss RA, Platz MS, Jones M. John Wiley & Sons, Inc; New York: 2005: 375
- 23 Stephan DW, Erker G. Angew. Chem. Int. Ed. 2015; 54: 6400
- 24 Frey GD, Lavallo V, Donnadieu B, Schoeller WW, Bertrand G. Science 2007; 316: 439
- 25 Hudnall TW, Moerdyk JP, Bielawski CW. Chem. Commun. 2010; 46: 4288
- 26 Auth J, Padevet J, Mauleón P, Pfaltz A. Angew. Chem. 2015; 127: 9678
- 27 van der Vlugt JI. Chem. Soc. Rev. 2010; 39: 2302
- 28 Moerdyk JP, Blake GA, Chase DT, Bielawski CW. J. Am. Chem. Soc. 2013; 135: 18798
- 29 Frey GD, Masuda JD, Donnadieu B, Bertrand G. Angew. Chem. Int. Ed. 2010; 49: 9444
- 30 Ueng S.-H, Solovyev A, Yuan X, Geib SJ, Fensterbank L, Lacôte E, Malacria M, Newcomb M, Walton JC, Curran DP. J. Am. Chem. Soc. 2009; 131: 11256
- 31 Chase DT, Moerdyk JP, Bielawski CW. Org. Lett. 2014; 16: 812
- 32 Peruzzini M, Gonsalvi L, Romerosa A. Chem. Soc. Rev. 2005; 34: 1038
- 33a Masuda JD, Schoeller WW, Donnadieu B, Bertrand G. Angew. Chem. Int. Ed. 2007; 46: 7052
- 33b Masuda JD, Schoeller WW, Donnadieu B, Bertrand G. J. Am. Chem. Soc. 2007; 129: 14180
- 34a Wanzlick H.-W, Schikora E. Chem. Ber. 1961; 94: 2389
- 34b Wanzlick H.-W, Kleiner H.-J. Chem. Ber. 1963; 96: 3024
- 34c Wanzlick H.-W, Ahrens H. Chem. Ber. 1966; 99: 1580
- 34d Arduengo AJ. III, Calabrese JC, Davidson F, Rasika Dias HV, Goerlich JR, Krafczyk R, Marshall WJ, Tamm M, Schmutzler R. Helv. Chim. Acta 1999; 82: 2348
- 34e Solé S, Gornitzka H, Schoeller WW, Bourissou D, Bertrand G. Science 2001; 292: 1901
- 34f Vignolle J, Asay M, Miqueu K, Bourissou D, Bertrand G. Org. Lett. 2008; 10: 4299
- 35 Giffin NA, Makramalla M, Hendsbee AD, Robertson KN, Sherren C, Pye CC, Masuda JD, Clyburne JA. C. Org. Biomol. Chem. 2011; 9: 3672
- 36 McKenzie I, Brodovitch J.-C, Percival PW, Ramnial T, Clyburne JA. C. J. Am. Chem. Soc. 2003; 125: 11565
- 37 Moerdyk JP, Bielawski CW. J. Am. Chem. Soc. 2012; 134: 6116
For CO fixation at various carbene centers, see:
For CO2 fixation at various carbene centers, see:
For catalytic CO2 conversion using various NHC catalysts, see:
For inter- and intramolecular C–H activation at various carbene centers, see: