Abstract
A facile and efficient synthesis of bibenzyl and biaryl derivatives by reductive homocoupling reaction is described. Treatment of benzyl and aryl halides with metallic zinc and copper powder in the presence of a catalytic amount of [C12mim][CuCl2] under ligand- and base-free conditions gives the corresponding bibenzyls and biaryls in good to high yields. The product can be isolated by a simple extraction with organic solvent, and the catalytic system can be recycled or reused without any significant loss of catalytic activity.
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Miyaura N, Suzuki A (1995) Chem Rev 95:2457
Zhu SS, Swager TM (1996) Adv Mater 8:497
Papillon J, Schulz E, Gelinas S, Lessard J, Lemaire M (1998) Synth Met 96:155
Fanta PE (1974) Synthesis 1974:9
Hassan J, Sevignon M, Gozzi C, Schulz E, Lemaire M (2002) Chem Rev 102:1359
Kuroboshi M, Waki Y, Tanaka H (2003) J Org Chem 68:3938
Nun P, Martinez J, Lamaty F (2009) Synlett 2009:1761
Kirchhoff JH, Netherton MR, Hill ID, Fu GC (2002) J Am Chem Soc 124:13662
Fujihara T, Yoshida S, Terao J, Tsuji Y (2009) Org Lett 11:2121
Silva AC, Senra JD, Aguiar LCS, Simas ABC, de Souza ALF, Malta LFB, Antunes OAC (2010) Tetrahedron Lett 51:3883
So CM, Yeung CC, Lau CP, Kwong FY (2008) J Org Chem 73:7803
Li HL, Wu ZS, Yang M, Qi YX (2010) Catal Lett 137:69
Simpson CD, Mattersteig G, Martin K, Gherghel L, Bauer RE, Rader HJ, Mullen K (2004) J Am Chem Soc 126:3139
King BT, Kroulík J, Robertson CR, Rempala P, Hilton CL, Korinek JD, Gortari LM (2007) J Org Chem 72:2279
Patrick TB, Willaredt RP, de Gonia DJ (1985) J Org Chem 50:2232
Smith MB, March J (1992) In: Carey FA, Sundberg RJ (eds) Advanced organic chemistry, 4th ed. Wiley, New York, p 715
Santos LS, Rosso GB, Pilli RA, Eberlin MN (2007) J Org Chem 72:5809
Coelho AV, de Souza ALF, de Lima PG, Wardell JL, Antunes OAC (2007) Tetrahedron Lett 48:7671
Imperato G, Vasold R, Konig B (2006) Adv Synth Catal 348:2243
Mee SPH, Lee V, Baldwin JE (2005) Chem Eur J 11:3294
Becht JM, Gissot A, Wagner A, Mioskowski C (2004) Tetrahedron Lett 45:9331
Johnson DK, Ciavarri JP, Ishmael FT, Schillinger KJ, van Geel TAP, Stratton SM (1995) Tetrahedron Lett 36:8565
Becht JM, Catala C, Drian CL, Wagner A (2007) Org Lett 9:1781
Mukhopadhyay S, Rothenberg G, Gitis D, Sasson Y (2000) J Org Chem 65:3107
Goossen LJ, Rodriguez N, Melzer B, Linder C, Deng G, Levy LM (2007) J Am Chem Soc 129:4824
Robinson MK, Kochurina VS Jr, Hanna JM (2007) Tetrahedron Lett 48:7687
Jutand A (2008) Chem Rev 108:2300
Adamo C, Amatore C, Ciofini I, Jutand A, Lakmini H (2006) J Am Chem Soc 128:6829
Hashim J, Kappe CO (2007) Adv Synth Catal 349:2353
Inaba S, Matsumoto H, Rieke RD (1984) J Org Chem 49:2093
Raynal F, Barhdadi R, Perichon J, Savall A, Troupel M (2002) Adv Synth Catal 344:45
Everson DA, Shrestha R, Weix DJ (2010) J Am Chem Soc 132:920
Kazuhiko O, Junzo Y, Harukichi H (1970) Bull Chem Soc Jpn 439:836
Khurana JM, Sushma C, Maikap GC (2003) Org Biomol Chem 1:1337
Sustmann R, Kopp C (1988) J Organomet Chem 347:313
Eisch JJ, Fregene PO (2008) Eur J Org Chem 2008:4482
Nishino T, Watanabe T, Okada M, Nishiyama Y, Sonoda N (2002) J Org Chem 67:966
Mukhopadhyay S, Rothenberg G, Gitis D, Baidossi M, Ponde DE, Sasson Y (2000) J Chem Soc Perkin Trans 2:1809
Mukhopadhyay S, Rothenberg G, Gitis D, Sasson Y (2000) Org Lett 2:211
Qian YL, Li GS, Huang YZ (1990) J Organomet Chem 381:29
Moncomble A, Floch PL, Gosmini C (2009) Chem Eur J 15:4770
Barrero AF, Herrador MM, Moral JFQ, Arteaga P, Akssira M, Hanbali FE, Arteaga JF, Dieguez HR, Sanchez EM (2007) J Org Chem 72:2251
Barrero AF, Herrador MM, Moral JFQ, Arteaga P, Arteaga JF, Dieguez HR, Sanchez EM (2007) J Org Chem 72:2988
Dahlen A, Prasad E, Flowers RA II, Hilmersson G (2005) Chem Eur J 11:3279
Rogers RD, Seddon KR (2005) Ionic liquids: fundamentals, progress, challenges, and opportunities. American Chemical Society, Washington
Zhang SJ, Lu XM (2006) Ionic liquids: from fundamental research to industrial applications. Science Press, Beijing
Wasserschein P, Welton T (2008) Ionic liquids in synthesis. Wiley-VCH, Weinheim
Blaszczyk I, Trzeciak AM, Ziolkowski JJ (2009) Catal Lett 133:262
Wang W, Cheng W, Shao L, Yang J (2008) Catal Lett 121:77
Roberts NJ, Lye GJ (2002) Application of room temperature ionic liquids in biocatalysis: opportunities and challenges. American Chemical Society, Washington
Mac Farlane DR, Forsyth M, Howlett PC, Pringle JM, Sun JZ, Annat G, Neil W, Izgorodina EI (2007) Acc Chem Res 40:1165
Meng Y, Pino V, Anderson JL (2009) Anal Chem 81:7107
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We thank the National Basic Research Program (973) of China (No. 613740101) and Natural Science Foundation of Jiangsu Province for support of this research.
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Hu, YL., Li, F., Gu, GL. et al. Facile and Efficient Reductive Homocoupling of Benzyl and Aryl Halides Catalyzed by Ionic Liquid [C12mim][CuCl2] in the Presence of Metallic Zinc and Copper. Catal Lett 141, 467–473 (2011). https://doi.org/10.1007/s10562-010-0535-5
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DOI: https://doi.org/10.1007/s10562-010-0535-5