N-heterocyclic carbene catalyzed carba-, sulfa-, and phospha-Michael additions with NHC·CO2 adducts as precatalysts

Addition reactions; Carboxylation; Catalysis; Organic compounds; Azolium salts; Michael additions; N-heterocyclic carbenes; Precatalysts; Carbon dioxide; Michael addition

Abstract :

[en] N-heterocyclic carbene catalyzed Michael additions have been revisited with 1,3-dialkyl- or 1,3-diarylimidazol(in)ium-2-carboxylates, that is, NHC·CO2 adducts, as the source of the free NHC catalysts in solution. Using these precatalysts, a number of efficient carba-, sulfa-, and phospha-Michael additions were achieved very conveniently, without the need for an external strong base to generate the NHC by deprotonation of an azolium salt. To further expand the scope of the procedure, some NHC-catalyzed sulfa-Michael/aldol organocascades were also investigated.

Disciplines :

Chemistry

Author, co-author :

Hans, Morgan ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique

Delaude, Lionel ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie organométallique et catalyse homogène

Rodriguez, Jean; Aix Marseille Université, Centrale Marseille, CNRS, 13397 Marseille, France

Coquerel, Yoann; Aix Marseille Université, Centrale Marseille, CNRS, 13397 Marseille, France

Language :

English

Title :

N-heterocyclic carbene catalyzed carba-, sulfa-, and phospha-Michael additions with NHC·CO2 adducts as precatalysts

Publication date :

2014

Journal title :

Journal of Organic Chemistry

ISSN :

0022-3263

eISSN :

1520-6904

Publisher :

American Chemical Society, Washington, United States - District of Columbia

Volume :

Issue :

Pages :

2758-2764

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 28 April 2014

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Bibliography

N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient Synthetic Tools; Díez-González, S., Ed.; Royal Society of Chemistry: Cambridge, U.K., 2010.
Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis; Cazin, C. S. J., Ed.; Springer: Dordrecht, The Netherlands, 2011.
Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606
Grossmann, A.; Enders, D. Angew. Chem., Int. Ed. 2012, 51, 314
Ryan, S. J.; Candish, L.; Lupton, D. W. Chem. Soc. Rev. 2013, 42, 4906
Bugaut, X.; Glorius, F. Chem. Soc. Rev. 2012, 41, 3511
For recent work, see: Nawaz, F.; Zaghouani, M.; Bonne, D.; Chuzel, O.; Rodriguez, J.; Coquerel, Y. Eur. J. Org. Chem. 2013, 8253
Grasa, G. A.; Güveli, T.; Singh, R.; Nolan, S. P. J. Org. Chem. 2003, 68, 2812
Chen, X.-Y.; Ye, S. Org. Biomol. Chem. 2013, 11, 7991
Douglas, J.; Churchill, G.; Smith, A. D. Synthesis 2012, 44, 2295
Hans, M.; Wouters, J.; Demonceau, A.; Delaude, L. Chem. Eur. J. 2013, 19, 9668
Fèvre, M.; Pinaud, J.; Vignolle, J.; Gnanou, Y.; Taton, D. Chem. Soc. Rev. 2013, 42, 2142
Dröge, T.; Glorius, F. Angew. Chem., Int. Ed. 2010, 49, 6940
Amyes, T. L.; Diver, S. T.; Richard, J. P.; Rivas, F. M.; Toth, K. J. Am. Chem. Soc. 2004, 126, 4366
Higgins, E. M.; Sherwood, J. A.; Lindsay, A. G.; Armstrong, J.; Massey, R. S.; Alder, R. W.; O'Donoghue, A. C. Chem. Commun. 2011, 47, 1559
Massey, R. S.; Collett, C. J.; Lindsay, A. G.; Smith, A. D.; O'Donoghue, A. C. J. Am. Chem. Soc. 2012, 134, 20421
Boddaert, T.; Coquerel, Y.; Rodriguez, J. Adv. Synth. Catal. 2009, 351, 1744
Adv. Synth. Catal. 2009, 351, 2541. (corrigendum)
Boddaert, T.; Coquerel, Y.; Rodriguez, J. Chem. Eur. J. 2011, 17, 2266
Phillips, E. M.; Riedrich, M.; Scheidt, K. A. J. Am. Chem. Soc. 2010, 132, 13179
Kang, Q.; Zhang, Y. Org. Biomol. Chem. 2011, 9, 6715
Enders, D.; Lüttgen, K.; Narine, A. A. Synthesis 2007, 959
Enders, D.; Saint-Dizier, A.; Lannou, M.-I.; Lenzen, A. Eur. J. Org. Chem. 2006, 29
Greenberg, S.; Stephan, D. W. Chem. Soc. Rev. 2008, 37, 1482
Delaude, L. Eur. J. Inorg. Chem. 2009, 1681
Van Ausdall, B. R.; Glass, J. L.; Wiggins, K. M.; Aarif, A. M.; Louie, J. J. Org. Chem. 2009, 74, 7935
Voutchkova, A. M.; Appelhans, L. N.; Chianese, A. R.; Crabtree, R. H. J. Am. Chem. Soc. 2005, 127, 17624
Voutchkova, A. M.; Feliz, M.; Clot, E.; Eisenstein, O.; Crabtree, R. H. J. Am. Chem. Soc. 2007, 129, 12834
Tudose, A.; Demonceau, A.; Delaude, L. J. Organomet. Chem. 2006, 691, 5356
Sauvage, X.; Demonceau, A.; Delaude, L. Adv. Synth. Catal. 2009, 351, 2031
Naik, P. U.; Petitjean, L.; Refes, K.; Picquet, M.; Plasseraud, L. Adv. Synth. Catal. 2009, 351, 1753
Pinaud, J.; Vignolle, J.; Gnanou, Y.; Taton, D. Macromolecules 2011, 44, 1900
Fèvre, M.; Coupillaud, P.; Miqueu, K.; Sotiropoulos, J.-M.; Vignolle, J.; Taton, D. J. Org. Chem. 2012, 77, 10135
Duong, H. A.; Cross, M. J.; Louie, J. Org. Lett. 2004, 6, 4679
Bantu, B.; Pawar, G. M.; Wurst, K.; Decker, U.; Schmidt, A. M.; Buchmeiser, M. R. Eur. J. Inorg. Chem. 2009, 1970
Naik, P. U.; Refes, K.; Sadaka, F.; Brachais, C.-H.; Boni, G.; Couvercelle, J.-P.; Picquet, M.; Plasseraud, L. Polym. Chem. 2012, 3, 1475
Fèvre, M.; Pinaud, J.; Leteneur, A.; Gnanou, Y.; Vignolle, J.; Taton, D.; Miqueu, K.; Sotiropoulos, J.-M. J. Am. Chem. Soc. 2012, 134, 6776
Ortega, N.; Richter, C.; Glorius, F. Org. Lett. 2013, 15, 1776
Brandau, S.; Maerten, E.; Jørgensen, K. A. J. Am. Chem. Soc. 2006, 128, 14986
Stockland, R. A., Jr.; Taylor, R. I.; Thompson, L. E.; Patel, P. B. Org. Lett. 2005, 7, 851
Lenker, H. K.; Richard, M. E.; Reese, K. P.; Carter, A. F.; Zawisky, J. D.; Winter, E. F.; Bergeron, T. W.; Guydon, K. S.; Stockland, R. A., Jr. J. Org. Chem. 2012, 77, 1378
Tye, H.; Skinner, C. L. Helv. Chim. Acta 2002, 85, 3272
Khan, A. T.; Ghosh, S.; Choudhury, L. H. Eur. J. Org. Chem. 2006, 2226
Gelat, F.; Jayashankaran, J.; Lohier, J.-F.; Gaumont, A.-C.; Perrio, S. Org. Lett. 2011, 13, 3170
Markus, J.; Bernd, P. Chem. Eur. J. 2011, 17, 10417
Rajabi, F.; Saidi, M. R. J. Sulfur Chem. 2005, 26, 251
Chu, C.-M.; Gao, S.; Sastry, M. N. V.; Kuo, C.-W.; Lu, C.; Liu, J.-T.; Yao, C.-F. Tetrahedron 2007, 63, 1863
Clarke, C.; Foussat, S.; Fox, D. J.; Sejer Pedersen, D.; Warren, S. Org. Biomol. Chem. 2009, 7, 1323
Trepohl, V. T.; Mori, S.; Itami, K.; Oestreich, M. Org. Lett. 2009, 11, 1091
Bateman, R. L.; Ashworth, J.; Witte, J. F.; Baker, L.-J.; Bhanumoorthy, P.; Timm, D. E.; Hurley, T. D.; Grompe, M.; McClard, R. W. Biochem. J. 2007, 402, 251
Carta, P.; Puljic, N.; Robert, C.; Dhimane, A.-L.; Fensterbank, L.; Lacôte, E.; Malacria, M. Org. Lett. 2007, 9, 1061
Martínez-Castro, E.; López, Ó.; Maya, I.; Fernández-Bolaños, J. G.; Petrini, M. Green Chem. 2010, 12, 1171
Keglevich, G.; Sipos, M.; Takács, D.; Greiner, I. Heteroat. Chem. 2007, 18, 226