Abstract
This short review presents an overview of the effectiveness of β-bromoaldehyde as synthetic tool in organic chemistry. Few groups have reported significant contributions on β-bromoaldehyde. The aim of our short review was to give an overview of the latest advances in the chemistry of β- bromoaldehyde from their preparation to their transformations and applications in organic synthesis of some heterocyclic and carbocyclic molecules by using palladium-catalyzed reaction.
Graphical Abstract
[1]
Sami, M.I.; Kar, G.K.; Ray, J.K. Synthesis and thermolysis of cycloalkenyl azides. A simple route to polycyclic isoxazoles. Org. Prep. Proced. Int., 1991, 23(2), 186-188.
[http://dx.doi.org/10.1080/00304949109458307]
[http://dx.doi.org/10.1080/00304949109458307]
[2]
Aubert, T.; Tabyaoui, B.; Farnier, M.; Guilard, R. New cyclopenta[b]-pyrroles and -pyridines by reaction of 2-azido- and 2-phosphoranylideneaminocyclopent-1-ene-1-carbaldehydes with aliphatic esters. J. Chem. Soc., Perkin Trans. 1, 1989, 1(8), 1369-1373.
[http://dx.doi.org/10.1039/p19890001369]
[http://dx.doi.org/10.1039/p19890001369]
[3]
Kar, G.K.; Karmakar, A.C.; Ray, J.K. Regioselective cyclisation of anil derivatives-A short. Tetrahedron Lett., 1989, 30(2), 223-224.
[http://dx.doi.org/10.1016/S0040-4039(00)95165-7]
[http://dx.doi.org/10.1016/S0040-4039(00)95165-7]
[4]
Sami, I.; Kar, G.K.; Ray, J.K. Synthesis of polycyclic oxa-coumarins, potential antitumour agents and a short and convenient synthesis of naphthopyranoquinolines from naphthopyran chloroaldehydes. Tetrahedron, 1992, 48(24), 5199-5208.
[http://dx.doi.org/10.1016/S0040-4020(01)90128-0]
[http://dx.doi.org/10.1016/S0040-4020(01)90128-0]
[5]
Aubert, T.; Tabyaoui, B.; Farnier, M.; Guilard, R. A One-Pot Synthesis of 2-Substituted 2,4,5,6-Tetrahydrocyclopentapyrazoles. Synthesis, 1988, 1988(9), 742-743.
[http://dx.doi.org/10.1055/s-1988-27695]
[http://dx.doi.org/10.1055/s-1988-27695]
[6]
Kar, G.K.; Karmakar, A.C.; Ray, J.K. Studies on polycyclic thiaarenes: Part II. An improved synthesis of phenanthro[1,2- b]thiophene and a synthesis of acenaphtho[1,2- b]naphtho-[2,3- d]thiophene, a novel polynuclear thiaarene. J. Heterocycl. Chem., 1991, 28(4), 999-1002.
[http://dx.doi.org/10.1002/jhet.5570280428]
[http://dx.doi.org/10.1002/jhet.5570280428]
[7]
Coates, R.M.; Muskopf, J.W.; Senter, P.A. Synthesis of stereoisomeric 9a-methylhydrodicyclopenta[a,d]cyclooctan-1-ones related to the ophiobolins and ceroplastins via annelative ring expansion of hydrindene precursors. J. Org. Chem., 1985, 50(19), 3541-3557.
[http://dx.doi.org/10.1021/jo00219a022]
[http://dx.doi.org/10.1021/jo00219a022]
[9]
Tsuji, J. Organic Synthesiswith Palladium Compounds; Springer-Verlag: New York, 1980.
[http://dx.doi.org/10.1007/978-3-642-67475-4]
[http://dx.doi.org/10.1007/978-3-642-67475-4]
[11]
Larock, R.C. Advances in Metal-Organic Chemistry; Liebeskind, L.S., Ed.; JAI Press: London, 1994, Vol. V, .
[12]
Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis; Wiley and Sons: New York, 1995.
[14]
Negishi, E. Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley and Sons: New York, 2002, p. 1 and 2.
[15]
Imbos, R.; Minnaard, A.J.; Feringa, B.L. A highly enantioselective intramolecular Heck reaction with a monodentate ligand. J. Am. Chem. Soc., 2002, 124(2), 184-185.
[http://dx.doi.org/10.1021/ja017200a] [PMID: 11782165]
[http://dx.doi.org/10.1021/ja017200a] [PMID: 11782165]
[16]
Larock, R.C.; Yang, H.; Pace, P.; Cacchi, S.; Fabrizi, G. Palladium-catalyzed cross-coupling of unsaturated phenols with vinylic halides and triflates. Tetrahedron Lett., 1998, 39(3-4), 237-240.
[http://dx.doi.org/10.1016/S0040-4039(97)10502-0]
[http://dx.doi.org/10.1016/S0040-4039(97)10502-0]
[17]
Larock, R.C.; Yang, H.; Pace, P.; Narayanan, K.; Russell, C.E.; Cacchi, S.; Fabrizi, G. Synthesis of oxygen heterocycles via Pd-catalyzed cross-coupling of unsaturated phenols and vinylic halides or triflates. Tetrahedron, 1998, 54(26), 7343-7356.
[http://dx.doi.org/10.1016/S0040-4020(98)00399-8]
[http://dx.doi.org/10.1016/S0040-4020(98)00399-8]
[18]
Ma, S.; Negishi, E. Palladium-catalyzed cyclization of omega haloallenes A new general route to common, medium, and large ring compounds via cyclic carbopalladation. J. Am. Chem. Soc., 1995, 117(23), 6345-6357.
[http://dx.doi.org/10.1021/ja00128a025]
[http://dx.doi.org/10.1021/ja00128a025]
[19]
Ma, S.; Duan, D.; Shi, Z. Palladium(0)-catalyzed cyclization reaction of polymer-supported aryl iodides with 1,2-allenyl carboxylic acids. A facile solid-phase synthesis of butenolides. Org. Lett., 2000, 2(10), 1419-1422.
[http://dx.doi.org/10.1021/ol0057481] [PMID: 10814462]
[http://dx.doi.org/10.1021/ol0057481] [PMID: 10814462]
[20]
Ma, S.; Yu, Z. Efficient synthesis of bibutenolide derivatives through oxidative dimeric cyclization-coupling reaction of 2,3-allenoic acids. Org. Lett., 2003, 5(9), 1507-1510.
[http://dx.doi.org/10.1021/ol0342812] [PMID: 12713310]
[http://dx.doi.org/10.1021/ol0342812] [PMID: 12713310]
[21]
Rozhkov, R.V.; Larock, R.C. An efficient approach to dihydrofurocoumarins via palladium-catalyzed annulation of 1,3-dienes by o-iodoacetoxycoumarins. J. Org. Chem., 2003, 68(16), 6314-6320.
[http://dx.doi.org/10.1021/jo034571w] [PMID: 12895066]
[http://dx.doi.org/10.1021/jo034571w] [PMID: 12895066]
[22]
Rozhkov, R.V.; Larock, R.C. Synthesis of dihydrofurocoumarins via palladium-catalyzed annulation of 1,3-dienes by o-iodoacetoxycoumarins. Org. Lett., 2003, 5(6), 797-800.
[http://dx.doi.org/10.1021/ol027342p] [PMID: 12633074]
[http://dx.doi.org/10.1021/ol027342p] [PMID: 12633074]
[23]
Larock, R.C.; Doty, M.J.; Han, X. Palladium-catalyzed heteroannulation of internal alkynes by vinylic halides. Tetrahedron Lett., 1998, 39(29), 5143-5146.
[http://dx.doi.org/10.1016/S0040-4039(98)00982-4]
[http://dx.doi.org/10.1016/S0040-4039(98)00982-4]
[24]
Larock, R.C.; Han, X.; Doty, M.J. Synthesis of α-pyrones via palladium-catalyzed annulation of internal alkynes. Tetrahedron Lett., 1998, 39, 5713-5716.
[http://dx.doi.org/10.1016/S0040-4039(98)00982-4]
[http://dx.doi.org/10.1016/S0040-4039(98)00982-4]
[25]
Roesch, K.R.; Zhang, H.; Larock, R.C. Synthesis of isoquinolines and pyridines by the palladium-catalyzed iminoannulation of internal alkynes. J. Org. Chem., 2001, 66, 8042-8051.
[26]
Dai, G.; Larock, R.C. Synthesis of 3,4-disubstituted isoquinolines via palladium-catalyzed cross-coupling of o-(1-alkynyl)benzaldimines and organic halides. Org. Lett., 2001, 3(25), 4035-4038.
[http://dx.doi.org/10.1021/ol0102085] [PMID: 11735578]
[http://dx.doi.org/10.1021/ol0102085] [PMID: 11735578]
[27]
Dai, G.; Larock, R.C. Synthesis of 3,4-disubstituted isoquinolines via palladium-catalyzed cross-coupling of 2-(1-alkynyl)benzaldimines and organic halides. J. Org. Chem., 2003, 68(3), 920-928.
[http://dx.doi.org/10.1021/jo026294j] [PMID: 12558417]
[http://dx.doi.org/10.1021/jo026294j] [PMID: 12558417]
[28]
Žemlička, J.; Arnold, Z. Synthetic reactions of dimethylformamide. XI. Polyformylation of ketones of other types and the problem of the reaction course. Collect. Czech. Chem. Commun., 1961, 26(11), 2852-2864.
[http://dx.doi.org/10.1135/cccc19612852]
[http://dx.doi.org/10.1135/cccc19612852]
[29]
Jana, R.; Samanta, S.; Ray, J.K. Substrate dependent intramolecular palladium-catalysed cyclisation and subsequent β-H elimination or C-H activation: A general method for the synthesis of fused pyran rings. Tetrahedron Lett., 2008, 49(5), 851-854.
[http://dx.doi.org/10.1016/j.tetlet.2007.11.172]
[http://dx.doi.org/10.1016/j.tetlet.2007.11.172]
[30]
Jana, R.; Dewan, M.; Roymahapatra, G. Synthesis of fused pyran and tetracyclicpyran rings by intramolecular palladium-catalyzed β-H elimination and C-H bond Functionalization. ES Materials &. Manufacturing., 2021, 13, 40-52.
[31]
Ahmed, A.; Nuree, Y.; Ray, J.K. Aerobic ligand-free domino Suzuki coupling—Michael addition reaction catalyzed by in situ generated palladium nanoparticles in water: A general method for the synthesis of benzo[c]chromene derivatives. Tetrahedron Lett., 2013, 54(7), 665-668.
[http://dx.doi.org/10.1016/j.tetlet.2012.12.005]
[http://dx.doi.org/10.1016/j.tetlet.2012.12.005]
[32]
Ahmed, A.; Dhara, S.; Ray, J.K. Palladium-catalyzed and KO Bu-promoted Caryl-Oalcoholic coupling: An efficient one-pot synthesis of oxygen containing fused rings. Tetrahedron Lett., 2013, 54(13), 1673-1676.
[http://dx.doi.org/10.1016/j.tetlet.2013.01.062]
[http://dx.doi.org/10.1016/j.tetlet.2013.01.062]
[33]
Jana, R.; Chatterjee, I.; Samanta, S.; Ray, J.K. Novel and rapid palladium-assisted 6π electrocyclic reaction affording 9,10-dihydrophenanthrene and its analogues. Org. Lett., 2008, 10(21), 4795-4797.
[http://dx.doi.org/10.1021/ol801882t] [PMID: 18828592]
[http://dx.doi.org/10.1021/ol801882t] [PMID: 18828592]
[34]
Jana, R.; Dewan, M.; Roymahapatra, G. Synthesis of 9,10 -dihydrophenanthrine, phenanthrine, mono and dialkylphenanthrine and octa-hydro phenanthrine by palladium catalyzed heck reaction. ES Materials & amp. Manufacturing., 2021, 14, 51-58.
[35]
Lan, Y.; Wang, C.; Sowa, J.R., Jr; Wu, Y.D. A theoretical investigation on the mechanism of a palladium-mediated formal 6π electrocyclic synthesis of 9,10-dihydrophenanthrenes. J. Org. Chem., 2010, 75(3), 951-954.
[http://dx.doi.org/10.1021/jo902163v] [PMID: 20039689]
[http://dx.doi.org/10.1021/jo902163v] [PMID: 20039689]
[36]
Some, S.; Ray, J.K.; Banwell, M.G.; Jones, M.T. New protocols for the synthesis of 3,4-annulated and 4-substituted quinolines from β-bromo-α β-unsaturated aldehydes and 1-bromo-2-nitrobenzene or 2-bromoacetanilide. Tetrahedron Lett., 2007, 48(20), 3609-3612.
[http://dx.doi.org/10.1016/j.tetlet.2007.03.078]
[http://dx.doi.org/10.1016/j.tetlet.2007.03.078]
[37]
Ray, D.; Ray, J.K. Base-catalyzed condensation of β-bromovinylaldehydes with β-ketoesters followed by water-mediated cyclization and aromatization: One-pot access to substituted benzene derivatives. Tetrahedron Lett., 2007, 48(4), 673-676.
[http://dx.doi.org/10.1016/j.tetlet.2006.11.104]
[http://dx.doi.org/10.1016/j.tetlet.2006.11.104]
[38]
Ray, D.; Paul, S.; Brahma, S.; Ray, J.K. Palladium-catalyzed intramolecular 5-endo-trig oxidative Heck cyclization: a facile pathway for the synthesis of some sesquiterpene precursors. Tetrahedron Lett., 2007, 48(45), 8005-8008.
[http://dx.doi.org/10.1016/j.tetlet.2007.09.052]
[http://dx.doi.org/10.1016/j.tetlet.2007.09.052]
[39]
Ray, D.; Ray, J.K. Novel synthetic approach toward (+/-)-β-cuparenone via palladium-catalyzed tandem Heck cyclization of 1-bromo-5-methyl-1-aryl-hexa-1,5-dien-3-ol derivatives. Org. Lett., 2007, 9(2), 191-194.
[http://dx.doi.org/10.1021/ol062418t] [PMID: 17217262]
[http://dx.doi.org/10.1021/ol062418t] [PMID: 17217262]
[40]
Nandi, S.; Ray, J.K. Copper catalyzed synthesis of highly substituted pyrrole and isoindole derivatives. Tetrahedron Lett., 2011, 52(46), 6203-6206.
[http://dx.doi.org/10.1016/j.tetlet.2011.09.070]
[http://dx.doi.org/10.1016/j.tetlet.2011.09.070]
[41]
Nandi, S.; Samanta, S.; Jana, S.; Ray, J.K. Synthesis of substituted benzimidazo[2,1-a]isoquinolines and its condensed analogues using Pd(0)-catalyzed cyclization/C-H activation. Tetrahedron Lett., 2010, 51(40), 5294-5297.
[http://dx.doi.org/10.1016/j.tetlet.2010.07.162]
[http://dx.doi.org/10.1016/j.tetlet.2010.07.162]
[42]
Nandi, S.; Ray, J.K. Palladium-catalyzed cyclization/cyclopropanation reaction for the synthesis of fused N-containing heterocycles. Tetrahedron Lett., 2009, 50(50), 6993-6997.
[http://dx.doi.org/10.1016/j.tetlet.2009.09.156]
[http://dx.doi.org/10.1016/j.tetlet.2009.09.156]
[43]
Ray, J.K.; Singha, R.; Ray, D.; Ray, P.; Rao, D.Y.; Anoop, A. Palladium-catalyzed expedient Heck annulations in 1-bromo-1,5-dien-3-ols: Exceptional formation of fused bicycles. Tetrahedron Lett., 2019, 60(13), 931-935.
[http://dx.doi.org/10.1016/j.tetlet.2019.02.043]
[http://dx.doi.org/10.1016/j.tetlet.2019.02.043]
