Abstract
A highly efficient catalytic activity towards Heck and Suzuki cross-coupling reactions was observed for a palladium complex in ethyl-methyl imidazolium hexafluorophosphate, [EMIM] PF6 ionic liquid medium, at ambient temperature. The system provides a stable, reusable method for the reaction. The optimization for the suitable reactions conditions was explored, and the effect of substituents on boronic acid was investigated. Using a very modest amount of catalyst, good-to-excellent yields were achieved. The reaction conditions were mild and most importantly, the catalyst-ionic liquid mixture was easily recoverable and reused for six times without much loss in the catalytic activity, causing negligible impact on the environment.
References
Tsuji J (2004) Palladium reagents and catalysts. Wiley, Chichester
Chinchilla R, Nájera C (2014) Chem Rev 114:1783–1826
Johansson SCC, Kitching MO, Colacot TJ, Snieckus V (2012) Angew Chem Int Ed 51:5062–5085
Bermejo A, Ros A, Fernández R, Lassaletta JM (2008) J Am Chem Soc 130:15798–15799
Owusu MO, Handa S, Slaughter LM (2012) Appl Organomet Chem 26:712–717
Mori A, Miyakawa Y, Ohashi E, Haga T, Maegawa T, Sajiki H (2006) Org Lett 8:3279–3281
McIntosh AI, Watson DJ, Burton JW, Lambert RM (2006) J Am Chem Soc 128:7329–7334
Wang D-S, Wang D-W, Zhou Y-G (2011) Synlett 7:947–950
Karimi B, Akhavan PF (2011) Inorg Chem 50:6063–6072
Chinchilla R, Nájera C (2007) Chem Rev 107:874–922
Fors BP, Buchwald SL (2010) J Am Chem Soc 132:15914–15917
Tardiff BJ, McDonald R, Ferguson MJ, Stradiotto M (2012) J Org Chem 77:1056–1071
Dai W, Chalkley MJ, Brudvig GW, Hazari N, Melvin PR, Pokhrel R, Takase MK (2013) Organometallics 32:5114–5127
Degtyareva ES, Burykina JV, Fakhrutdinov AN, Gordeev EG, Khrustalev VN, Ananikov VP (2015) ACS Catal 5:7208–7213
Benhamou L, Besnard C, Kündig EP (2014) Organometallics 33:260–266
Wang T, Hao X-Q, Huang J-J, Wang K, Gong J-F, Song M-P (2014) Organometallics 33:194–205
Hashmi ASK, Hengst T, Lothschüt C, Rominger F (2010) Adv Synth Catal 352:1315–1337
Newman SG, Lautens M (2010) J Am Chem Soc 132:11416–11417
Mu X, Chen S, Zhen X, Liu G (2011) Chem-Eur J 17:6039–6042
Wu XF, Neumann H, Beller M (2013) Chem Rev 113:1–35
Magano J, Dunetz JR (2011) Chem Rev 111:2177–2250
Torborg C, Beller M (2009) Adv Synth Catal 351:3027–3043
Ranganath KVS, Onitsuka S, Kumar AK, Inanaga J (2013) Catal Sci Technol 3:2161–2181
Corbet JP, Mignani G (2006) Chem Rev 106:2651–2710
Milhau L, Guiry PJ (2012) In transition metal catalyzed enantioselective allylic substitution in organic synthesis. In: Kazmaier U (ed) Topics in organometallic chemistry 38. Springer, Berlin
Schlummer B, Scholz U (2004) Adv Synth Catal 346:1599–1626
Miao W, Chan TH (2006) Acc Chem Res 39:897–908
Handy ST, Okello M (2005) J Org Chem 70:2874–2877
Chemler SR, Trauner D, Danishefsky SJ (2001) Angew Chem Int Ed 40:4544–4568
Suzuki A (2011) Angew Chem Int Ed 50:6722–6737
Yang DX, Colletti SL, Wu K, Song MY, Li GY, Shen HC (2009) Org Lett 11:381–384
Jo TS, Kim SH, Shin J, Bae C (2009) J Am Chem Soc 131:1656–1657
Polshettiwar V, Decottignies A, Len C, Fihri A (2010) Chemsuschem 3:502–522
Liu GC, Huang JJ, Zhang JW, Wang XL, Lin HY (2013) Trans Met Chem 38:359–365
Yao Q, Kinney EP, Yang Z (2003) J Org Chem 68:7528–7531
Liu L, Zhang Y, Xin B (2006) J Org Chem 71:3994–3997
Reetz MT, de Vries JG (2004) Chem Commun 14:1559–1563
Karimi B, Enders D (2006) Org Lett 8:1237–1240
Stevens PD, Li G, Fan J, Yen M, Gao Y (2005) Chem Commun 35:4435–4437
Astruc D, Lu F, Aranzaes JR (2005) Angew Chem Int Ed 44:7852–7872
Polshettiwar V, Molnár Á (2007) Tetrahedron 63:6949–6976
Ramakrishna D, Bhat BR (2010) Appl. Organometal Chem 24:663–666
Lipshutz BH, Petersen TB, Abela AR (2008) Org Lett 10:1333–1336
Byrne FP, Jin S, Paggiola G, Petchey THM, Clark JH, Farmer TJ, Hunt AJ, McElroy CR, Sherwood J (2016) Sustain Chem Process 4:7
DeVasher RB, Moore LR, Shaughnessy KH (2004) J Org Chem 69:7919–7927
Nehra P, Khungar B, Pericherla K, Sivasubramanian SC (2014) Anil Kumar. Green Chem 16:4266–4271
Baran T (2018) Carbohydr Polym 195:45–52
Baran T, Nuray YB, Ayfer M (2018) Int J Biol Macromol 115:249–256
Baran T (2018) Ultrason Sonochem 45:231–237
Baran T, Nuray YB, Ayfer M (2018) J Mol Struct 1160:154–160
Baran T, Idris S, Murat K, Ayfer M (2016) J Mol Cat A 420:216–221
Baran T, Eda A, Ayfer M (2015) J Mol Cat A 407:47–52
Karthikeyan P, Vanitha A, Radhika P, Suresh K, Sugumaran A (2013) Tetrahedron Lett 54:7193–7197
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DR would like to thank the IISc Bangalore for all the spectroscopic analyses.
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Ramakrishna, D. An Ionic Liquid Immobilized Palladium Complex for an Effective Heck and Suzuki Coupling Reactions. Chemistry Africa 2, 21–28 (2019). https://doi.org/10.1007/s42250-018-00038-7
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DOI: https://doi.org/10.1007/s42250-018-00038-7