Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Tribromoisocyanuric Acid as a Green Cohalogenating Reagent: An Efficient Transformation of Alkynes into α,α-Dibromoketones and Vicinal Dibromoalkenes

Author(s): Lívia T.C. Crespo, Mônica R. Senra, Pierre M. Esteves* and Marcio C.S. de Mattos*

Volume 16, Issue 8, 2019

Page: [627 - 632] Pages: 6

DOI: 10.2174/1570178615666180803152951

Price: $65

Abstract

The co-halogenation reaction of alkynes with tri-bromoisocyanuric acid in acetic acid, followed by aqueous work-up produced α,α-di-bromoketones (44-84%), while the reaction in aqueous acetonitrile in the presence of KBr produced vicinal di-bromoalkenes (66-86%). The usefulness of the methodology was demonstrated employing green metrics for the comparison of TBCA with analogous N-halo reagents in co-halogenation reactions of alkynes.

Keywords: Bromination, electrophilic addition, halogenation, regioselectivity, green chemistry, alkenes, alkynes, ketones.

« Previous Next »
Graphical Abstract

[1]
(a) de Almeida, L.S.; Esteves, P.M.; de Mattos, M.C.S. Curr. Green Chem., 2014, 1, 94-107.
(b) Saikia, I.; Borah, A.J.; Phukan, P. Chem. Rev., 2016, 116, 6837-7042.
[2]
(a) de Almeida, L.S.; Esteves, P.M.; de Mattos, M.C.S. Synthesis, 2006, 2, 221-223.
(b) Mendonça, G.F.; Sindra, H.; de Almeida, L.S.; Esteves, P.M.; de Mattos, M.C.S. Tetrahedron Lett., 2009, 50, 3001-3004.
(c) Mendonça, G.F.; Sindra, H.; de Almeida, L.S.; Esteves, P.M.; de Mattos, M.C.S. Tetrahedron Lett., 2009, 50, 473-475.
(d) de Almeida, L.S.; de Mattos, M.C.S.; Esteves, P.M. Synlett, 2013, 24, 603-606.
[3]
de Almeida, L.S.; Esteves, P.M.; de Mattos, M.C.S. Tetrahedron Lett., 2015, 56, 6843-6845.
[4]
de Andrade, V.S.C.; de Mattos, M.C.S. J. Braz. Chem. Soc., 2014, 25, 975-979.
[5]
Sindra, H.C.; de Mattos, M.C.S. J. Braz. Chem. Soc., 2016, 27, 1129-1136.
[6]
de Andrade, V.S.C.; de Mattos, M.C.S. Synthesis, 2016, 48, 1381-1388.
[7]
Sodré, L.R.; Esteves, P.M.; de Mattos, M.C.S. J. Braz. Chem. Soc., 2013, 24, 212-218.
[8]
(a) Zolfigol, M.A.; Chehardoli, G.; Ghaemi, E.; Madrakian, E.; Zare, R.; Azadbakht, T.; Niknam, K.; Mallakpour, S. Monatsh. Chem., 2008, 139, 261-265.
(b) Habibi, D.; Zolfigol, M.A.; Faraji, A.R.; Rahmani, P. Monatsh. Chem., 2012, 143, 809-814.
(c) Crespo, L.T.C.; de Mattos, M.C.S.; Esteves, P.M. Quim. Nova, 2013, 36, 320-323.
[9]
de Almeida, L.S.; Esteves, P.M.; de Mattos, M.C.S. Synlett, 2006, 1515-1518.
[10]
Anastas, P.T.; Warner, J.C. Green Chemistry: Theory and Practice; Oxford University Press: Oxford, 2000.
[11]
Tozetti, S.D.; de Almeida, L.S.; Esteves, P.M.; de Mattos, M.C.S. J. Braz. Chem. Soc., 2007, 18, 675-677.
[12]
Trost, B.M. Science, 1991, 254, 1471-1477.
[13]
(a) Rodriguez, J.; Dulcère, J.P. Synthesis, 1993, 12, 1177-1205.
(b) Cheng, Y.A.; Yu, W.Z.; Yeung, Y.Y. Org. Biomol. Chem., 2014, 12, 2333-2343.
[14]
(a) Rajbongshi, K.K.; Phukan, P. Tetrahedron Lett., 2014, 55, 1877-1878.
(b) Okamoto, N.; Sueda, T.; Minami, H.; Miwa, Y.; Yanada, R. Org. Lett., 2015, 17, 1336-1339.
[15]
(a) Wang, J-Y.; Jiang, Q.; Guo, C-C. Synth. Commun., 2014, 44, 3130-3138.
(b) Tomoya, N.; Hirashima, S-I.; Tada, N.; Miura, T.; Itoh, A. Tetrahedron Lett., 2010, 51, 4576-4578.
(c) Moran, W.J.; Aborways, M.M. Tetrahedron Lett., 2014, 55, 2127-2129.
[16]
(a) Xiang, J.; Yuan, R.; Wang, R.; Yi, N.; Lu, L.; Zou, H.; He, W. J. Org. Chem., 2014, 79, 11378-11382.
(b) Beck, T.M.; Haller, H.; Streuff, J.; Riedel, S. Synthesis, 2014, 46, 740-747.
(c) Adimurthy, S.; Ghosh, S.; Patoliya, P.U.; Ramachandraiah, G.; Agrawal, M.; Gandhi, M.R.; Upadhyay, S.C.; Ghosh, P.K.; Ranu, B.C. Green Chem., 2008, 10, 232-237.
[17]
Paul, B.; Bhuyan, B.; Purkayastha, D.D.; Dhar, S.S.; Patel, B.K. Tetrahedron Lett., 2015, 56, 5646-5650.
[18]
Zhang, X.; Wu, Y.; Zhang, Y.; Liu, H.; Xie, Z.; Fu, S.; Liu, F. Tetrahedron, 2017, 73, 4513-4518.
[19]
(a) Sanabria, C.M.; Costa, B.B.S.; Viana, G.M.; de Aguiar, L.C.S.; de Mattos, M.C.S. Synthesis, 2018, 50, 1359-1367.
(b) Sanabria, C.M.; do Casal, M.T.; de Souza, R.B.A.; de Aguiar, L.C.S.; de Mattos, M.C.S. Synthesis, 2017, 49, 1648-1654.
[20]
Chen, Z.W.; Li, J.H.; Jiang, H.F.; Zhu, S.F.; Li, Y.B.; Qi, C.R. Org. Lett., 2010, 12, 3262-3265.
[21]
Crespo, L.T.C.; Nogueira, G.P.; de Mattos, M.C.S.; Esteves, P.M. Arkivoc, 2018, 205-214.
[22]
Hiegel, G.A.; Abdala, M.H.; Burke, S.V.; Beard, D.P. J. Chem. Educ., 1987, 64, 156.
[23]
Crespo, L.T.C.; Ribeiro, R.S.; de Mattos, M.C.S.; Esteves, P.M. Synthesis, 2010, 14, 2379-2382.
[24]
Finkelstein, M.; Hart, S.A.; Moore, W.M.; Ross, S.D.; Eberson, L. J. Org. Chem., 1986, 51, 3548-3551.
[25]
Bock, H.; Rittmeyer, P.; Stein, U. Chem. Ber., 1986, 119, 3766-3781.
[26]
Cristiano, R.; Ma, K.; Pottanat, G.; Weiss, R.G. J. Org. Chem., 2009, 74, 9027-9033.
[27]
Lapkin, A.; Constable, D. Green Chemistry Metrics: Measuring and Monitoring Sustainable Processes; Wiley: New York, 2008.
[28]
Kumar, A.; Saxena, D.; Gupta, M.K. Green Chem., 2013, 15, 2699-2703.
[29]
Kotek, V.; Polak, P.; Tobrman, T. Monatsh. Chem., 2016, 14, 405-412.
[30]
Liu, J.; Li, W.; Wang, C.; Li, Y.; Li, Z. Tetrahedron Lett., 2011, 52, 4320-4323.
[31]
Chawla, R.; Singh, A.K.; Yadav, L.D.S. Synlett, 2013, 24, 1558-1562.
[32]
(a) Sheldon, R.A. Chem. Ind.(London), 1992, 23, 903-906.
(b) Sheldon, R.A. Chem. Ind.(London), 1997, 12-15.
[33]
Schuh, K.; Glorius, A. Synthesis, 2007, 15, 2297-2306.
[34]
Shao, L-X.; Shi, M. Synlett, 2006, 8, 1269-1271.
[35]
Zheng, Y.F.; Yu, J.; Yan, G.B.; Li, X.; Luo, S. Chin. Chem. Lett., 2011, 22, 1195-1198.
[36]
Niu, M.; Fu, H.; Jiang, Y.; Zhao, Y. Synthesis, 2008, 18, 2879-2882.
[37]
Pilli, R.A.; Robello, L.G. J. Braz. Chem. Soc., 2004, 15, 938-944.
[38]
Organ, M.G.; Ghasemi, H.; Valente, C. Tetrahedron, 2004, 60, 9453-9461.
[39]
Podgorsek, A.; Eissen, M.; Fleckenstein, J.; Stavber, S.; Zupan, M.; Iskra, J. Green Chem., 2009, 11, 120-126.
[40]
Hara, S.; Kato, T.; Suzuki, A. Synthesis, 1983, 12, 1005-1006.
[41]
Giménez-Agulló, N.; Sáenz de Pipaón, C.; Adriaenssens, L.; Filibian, M.; Martínez-Belmonte, M.; Escudero-Adán, E.C.; Carretta, P.; Ballester, P.; Galán-Mascarós, J.R. Chem. Eur. J., 2014, 20, 12817-12825.

Rights & Permissions Print Cite
Article Metrics
35
5
1
© 2024 Bentham Science Publishers | Privacy Policy