Abstract
Cesium carbonate is a type of alkali carbonate salt having a remarkable number of applications and has been demonstrated to be a mild inorganic base in organic synthesis. It has received much attention for its utility in C, N, O alkylation and arylation reactions. Cesium carbonate not only promotes successful carbonylation of alcohols and carbamination of amines, but also suppresses common side reactions traditionally encountered with other protocols. It is used also in six-membered annulation, intramolecular and intermolecular cyclizations, Suzuki coupling, aza-Henry, nucleophilic substitution, cross coupling and different cycloaddition reactions.
Similar content being viewed by others
References
Z. Blum, Acta Chem. Scand. 43, 248 (1989)
G. Dijstra, W.H. Kruizinga, R.M. Kellogg, J. Org. Chem. 52, 4230 (1987)
A. Ostrowicki, E. Koepp, F. Vogtle, in Topics in Current Chemistry, vol. 161, ed. by E. Weber, F. Vogtle (Springer, Heidelberg, 1992), p. 37
C. Galli, Org. Prep. Proced. Int. 24, 287 (1992)
A.A. Fadda, R. Rabie, Res. Chem. Intermed. 42, 771 (2016)
S. Bondock, R. Rabie, H.A. Etman, A.A. Fadda, Eur. J. Med. Chem. 43, 2122 (2008)
A.A. Fadda, R. Rabie, H.A. Etman, A.S. Fouda, Res. Chem. Intermed. 41, 7883 (2015)
A.A. Fadda, S. Bondock, R. Rabie, H.A. Etman, Turk. J. Chem. 32, 259 (2008)
W.H. Kruizinga, R.M. Kellogg, J. Am. Chem. Soc. 103, 5183 (1981)
O. Piepers, R.M. Kellogg, J. Chem. Soc. Chem. Commun. 107, 383 (1978)
D.A. Bors, M.J. Kaufman, A. Streitwieser, J. Am. Chem. Soc. 107, 6975 (1985)
T.E. Hogen-Esch, J. Smid, J. Am. Chem. Soc. 88, 318 (1966)
J.H. Exner, E.C. Steiner, J. Am. Chem. Soc. 96, 1782 (1974)
F. Li, J. Ma, N. Wang, J. Org. Chem. 79, 10447 (2014)
L. Guo, Y. Liu, W. Yao, X. Leng, Z. Huang, Org. Lett. 15, 1144 (2013)
J. Inoh, T. Satoh, S. Art, M. Miura, M. Nomura, Tetrahedron Lett. 39, 4673 (1998)
B. Liegault, I. Petrov, S.I. Gorelsky, K. Fagnou, J. Org. Chem. 75, 1047 (2010)
J.K. Laha, N. Dayal, R. Jain, K. Patel, J. Org. Chem. 79, 10899 (2014)
P. Zhou, Y. Ye, J. Ma, L. Zheng, Q. Tang, Y. Qiu, B. Song, Z. Qiu, P. Xu, Y. Liang, J. Org. Chem. 79, 6627 (2014)
F. Bonnaterre, M. Choussy, J. Zhu. Org. Lett. 8, 4351 (2006)
S.J. Mansfield, C.D. Campbell, M.W. Jones, E.A. Anderson, Chem. Commun. 51, 3316 (2015)
S.E. Kiruthika, P.T. Perumal, Org. Lett. 16, 484 (2014)
S. Urgaonkar, J.G. Verkade, Tetrahedron 60, 11837 (2004)
M. Nivsarkar, M.P. Kaushik, Catal. Commun. 6, 367 (2005)
H. Yu, Y. Jiang, Y. Fu, L. Liu, J. Am. Chem. Soc. 132, 18078 (2010)
R.A. Altman, A. Shafir, A. Choi, P.A. Lichtor, S.L. Buchwald, J. Org. Chem. 73, 284 (2008)
S. Putatunda, A. Chakraborty, C. R. Chim. 17, 1057 (2014)
R.J. Cohen, D.L. Fox, J.F. Eubank, R.N. Salvatore, Tetrahedron Lett. 44, 8617 (2003)
D.K. Leahy, S.K. Pack, Org. Process Res. Dev. 17, 1440 (2013)
T. Norris, K. Leeman, Org. Process Res. Dev. 12, 869 (2008)
F. Melkonyan, A. Topolyan, A. Karchava, M. Yurovskaya, Tetrahedron 67, 6826 (2011)
K. Kundu, S.K. Nayak, RSC Adv. 2, 480 (2012)
G.L. Simpson, T.P. Heffron, E. Merino, T.F. Jamison, J. Am. Chem. Soc. 128, 1056 (2006)
T.A. Moss, D.M. Barber, A.F. Kyle, D.J. Dixon, Chem. Eur. J. 19, 3071 (2013)
L. Donati, S. Michel, F. Tillequin, F. Poree, Org. Lett. 12, 156 (2010)
C. Li, W. Zhang, X. Wang, J. Org. Chem. 79, 5847 (2014)
S. Arai, R. Tsuji, A. Nishida, Tetrahedron Lett. 43, 9535 (2002)
C.J. Karinthi, F. Zouhiri, J. Mahuteau, D. Desmaele, Tetrahedron 59, 2093 (2003)
T.N. Poudel, Y.R. Lee, Org. Biomol. Chem. 12, 919 (2014)
K.S. Masters, M. Wallesch, S. Brase, J. Org. Chem. 76, 9060 (2011)
L. Ye, X. Sun, C. Zhu, Y. Tang, Org. Lett. 8, 3853 (2006)
S. De, L.K. Kinthada, A. Bisai, Synlett 23, 2785 (2012)
T. Zhu, C. Mou, B. Li, M. Smetankova, B.S.Y.R. Chi, J. Am. Chem. Soc. 137, 5658 (2015)
W. Ming, X. Liu, L. Wang, J. Liu, M. Wang, Org. Lett. 17, 1746 (2015)
K.A. Volp, A.M. Harned, J. Org. Chem. 78, 7554 (2013)
S. Tanimori, H. Ura, U. Inaba, H. Kashiwagi, T. Nishimura, Y. Kato, M. Kirihata, Res. Chem. Intermed. 40, 2157 (2014)
L. Wang, S. Peng, J. Wang, Chem. Commun. 47, 5422 (2011)
D. Enders, J. Han, A. Henseler, Chem. Commun. 40, 3989 (2008)
B. Li, C. Li, J. Org. Chem. 79, 2242 (2014)
R.B. Bedford, M. Betham, M.E. Blake, R.M. Frost, P.N. Horton, M.B. Hursthousec, R.L. Nicolásd, Dalton Trans. 16, 2774 (2005)
C. Palomo, M. Oiarbide, A. Laso, R. Lopez, J. Am. Chem. Soc. 127, 17622 (2005)
R. Imashiro, H. Uehara, C.F. Barbas, Org. Lett. 12, 5250 (2010)
T. Ishiyama, H. Kizaki, N. Miyaura, A. Suzuki, Tetrahedron Lett. 34, 7595 (1993)
A.O. Biying, V.R. Vangala, C.S. Chen, L.P. Stubs, N.S. Hosmane, Z. Yinghuai, Dalton Trans. 43, 5014 (2014)
G.W. Kabalka, G. Dong, B. Venkataiah, Tetrahedron Lett. 46, 763 (2005)
D.N. Primer, I. Karakaya, J.C. Tellis, G.A. Molander, J. Am. Chem. Soc. 137, 2195 (2015)
P.J. Black, G.C. Kobeci, M.G. Edwards, P.A. Slatford, M.K. Whittlesey, J.M.J. Williams, Org. Biomol. Chem. 4, 116 (2006)
M.G. Edwards, J.M.J. Williams, Angew. Chem. Int. Ed. 41(24), 4740 (2002)
K. Muto, J. Yamaguchi, A. Lei, K. Itami, J. Am. Chem. Soc. 135, 16384 (2013)
J. Chen, Y. Pu, H. Pei, L. He, S. Fu, L. Chen, Arch. Pharm. 347, 908 (2014)
J.F. Marcoux, S. Doye, S.L. Buchwald, J. Am. Chem. Soc. 119, 10539 (1997)
Y. Zhang, Y. Liu, J.P. Wan, New J. Chem. 39, 1567 (2015)
S. Mostarda, P. Filipponi, R. Sardella, F. Venturoni, B. Natalini, R. Pellicciari, A. Gioiello, Org. Biomol. Chem. 12, 9592 (2014)
H. Qrareya, S. Protti, M. Fagnoni, J. Org. Chem. 79, 11527 (2014)
A. Kondoh, H. Yorimitsu, K. Oshima, J. Am. Chem. Soc. 129, 4099 (2007)
L.S. Gong, C. Zhang, Q. Zheng, Y. Chen, Synlett 5, 0795 (2006)
R.K. Arigela, S.K. Sharma, B. Kumar, B.K. Beilstein, J. Org. Chem. 9, 401 (2013)
I. Ibrahem, P. Breistein, A. Cordova, Chem. Eur. J. 18, 5175 (2012)
C. Che, S. Lin, B. Yang, X. Jiang, T. Shao, Z. Yu, C. Tao, S. Li, J. Org. Chem. 79, 436 (2014)
B. Maleki, S.B.N. Chalaki, S.S. Ashrafi, E.R. Seresht, F. Moeinpour, A. Khojastehnezhad, R. Tayebee, Appl. Organometal. Chem. 29, 290 (2015)
C. Ma, Q. Zhang, K. Ding, L. Xin, D. Zhang, Tetrahedron Lett. 48, 7476 (2007)
A. Kondoh, H. Yorimitsu, K. Oshima, Tetrahedron 62, 2357 (2006)
D. Lee, J.H. Ko, K. Lee, Monat. Chem. 138, 741 (2007)
A.E. Rosamilia, F. Arico, P. Tundo, J. Org. Chem. 73, 1559 (2008)
M. Zhang, J. Guo, Y. Gong, Eur. J. Org. Chem. 2014, 1942 (2014)
S. Yugandar, A. Acharya, H. Ila, J. Org. Chem. 78, 3948 (2013)
L. Liu, J. Hu, X.C. Wang, M.J. Zhong, X.Y. Liu, S.D. Yang, Y.M. Liang, Tetrahedron 68, 5391 (2012)
Z.Y. Gu, T.H. Zhu, J.J. Cao, X.P. Xu, S.Y. Wang, S.J. Ji, ACS Catal. 4, 49 (2014)
Y. Que, T. Li, C. Yu, X.S. Wang, C. Yao, J. Org. Chem. 80, 3289 (2015)
Y. He, X. Zhang, X. Fan, Chem. Commun. 50, 14968 (2014)
W. Hao, Y. Jiang, M. Cai, J. Org. Chem. 79, 3634 (2014)
J. Qian, W. Yi, X. Huang, Y. Miao, J. Zhang, C. Cai, W. Zhang, Org. Lett. 17, 1090 (2015)
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare that they have no conflicts of interest.
Rights and permissions
About this article
Cite this article
Rabie, R., Hammouda, M.M. & Elattar, K.M. Cesium carbonate as a mediated inorganic base in some organic transformations. Res Chem Intermed 43, 1979–2015 (2017). https://doi.org/10.1007/s11164-016-2744-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-016-2744-z