Synthesis of chalcones via domino dehydrochlorination/Pd(OAc)2-catalyzed Heck reaction

doi:10.1016/S1872-2067(14)60247-3

Abstract

Abstract:

A new method has been developed for the cross-coupling of aryl halides with β-chloroalkyl aryl ketones and their ester and amide analogs through a domino dehydrochlorination/Pd(OAc)₂-catalyzed Heck reaction sequence. The enone intermediates generated in situ reduced the occurrence of side reactions and therefore enhanced the efficiency of the reaction. This reaction exhibited good tolerance to various functional groups on both substrates and provides rapid access to a wide range of chalcone derivatives.

Key words: β-Chloroalkyl aryl ketone, Heck reaction, Enone, Domino reaction, Chalcone

Tenglong Guo, Quanbin Jiang, Likun Yu, Zhengkun Yu. Synthesis of chalcones via domino dehydrochlorination/Pd(OAc)₂-catalyzed Heck reaction[J]. Chinese Journal of Catalysis, 2015, 36(1): 78-85.

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https://www.cjcatal.com/EN/Y2015/V36/I1/78

References

[1] Nowakowska Z. Eur J Med Chem, 2007, 42: 125
[2] Bandgar B P, Gawande S S, Bodade R G, Totre J V, Khobragade C N. Bioorg Med Chem, 2010, 18: 1364
[3] Sahu N K, Balbhadra S S, Choudhary J, Kohli D V. Curr Med Chem, 2012, 19: 209
[4] Ma S J, Wu L L, Liu M, Wang Y M. Org Biomol Chem, 2012, 10: 3721
[5] Patti A, Pedotti S, Grassi T, Idolo A, Guido M, De Donno A. J Organomet Chem, 2012, 716: 216.
[6] Ye Y, Wang H, Fan R H. Org Lett, 2010, 12: 2802
[7] Ribierre J C, Cheval G, Huber F, Mager L, Fort A, Muller R, Mery S, Nicoud J F. J Appl Phys, 2002, 91: 1710
[8] Ravindra H J, Kiran A J, Nooji S R. Dharmaprakash S M, Chandrasekharan K, Kalluraya B, Rotermund F. J Cryst Growth, 2008, 310: 2543
[9] Liu M, Wilairat P, Go M L. J Med Chem, 2001, 44: 4443
[10] Wu X F, Neumann H, Spannenberg A, Schulz T, Jiao H J, Beller M. J Am Chem Soc, 2010, 132: 14596
[11] Pennell M N, Unthank M G., Turner P, Sheppard T D. J Org Chem, 2011, 76: 1479
[12] Wang J, Liu C, Yuan J W, Lei A W. Angew Chem Int Ed, 2013, 52: 2256
[13] Yu S J, Li X W. Org Lett, 2014, 16: 1220
[14] Heck R F. Acc Chem Res, 1979, 12: 146
[15] Bianco A, Cavarischia C, Farina A, Marcella G, Carolina M. Tetrahedron Lett, 2003, 44: 9107
[16] Bianco A, Cavarischia C, Guiso M. Eur J Org Chem, 2004: 2894
[17] Yu J Q, Wu H C, Corey E J. Org Lett, 2005, 7: 1415.
[18] Uyanik M, Akakura M, Ishihara K. J Am Chem Soc, 2009, 131: 251
[19] Zhou J, Wu G, Zhang M, Jie X M, Su W P. Chem Eur J, 2012, 18: 8032
[20] Shang Y P, Jie X M, Zhou J, Hu P, Huang S J, Su W P. Angew Chem Int Ed, 2013, 52: 1299
[21] Unoh Y, Hirano K, Satoh T, Miura M. J Org Chem, 2013, 78: 5096
[22] Jiang Q B, Guo T L, Wang Q F, Wu P, Yu Z K. Adv Synth Catal, 2013, 355: 1874
[23] Guo T L, Jiang Q B, Huang F, Chen J P, Yu Z K. Org Chem Front, 2014, 1: 707
[24] Tietze L F. Chem Rev, 1996, 96: 115
[25] Ding B Q, Zhang Z F, Liu Y G, Sugiya M, Imamoto T, Zhang W B. Org Lett, 2013, 15: 3690
[26] Rajput J K, Kaur G. Tetrahedron Lett, 2012, 53: 646
[27] Batovska D, Parushev St, Slavova A, Bankova V, Tsvetkova I, Ninova M, Najdenski H. Eur J Med Chem, 2007, 42: 87
[28] Ranu B C, Jana R. J Org Chem, 2005, 70: 8621
[29] Lü P C, Sun J A, Luo Y, Yang Y, Zhu H L. Bioorg Med Chem Lett, 2010, 20: 4657
[30] Weber W M, Decka L M, Vander Jagtb D L. Bioorg Med Chem, 2006, 14: 2450
[31] Solomek T, Stacko P, Veetil A T, Pospisil T, Klan P. J Org Chem, 2010, 75: 7300
[32] Tsukerman S V; Bugai A I, Surov Yu N, Lavrushin V F, Pivnenko N S. Zhurnal Prikladnoi Spektroskopii, 1979, 31: 1036
[33] Reddy R S, Rosa J N, Veiros L F, Caddick S, Gois P M P. Org Biomol Chem, 2011, 9: 3126
[34] Ruiz D M, Romanelli G P, Bennardi D O, Baronetti G T, Thomas H J, Autino J C. ARKIVOC, 2008, 12: 269
[35] Munusamy R, Dhathathreyan K S, Balasubramanian K K, Venkatachalam C S. J Chem Soc, Perkin Trans 2, 2001: 1154

Synthesis of chalcones via domino dehydrochlorination/Pd(OAc)₂-catalyzed Heck reaction

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