Cross-Coupling Biarylation of Nitroaryl Chlorides Through High Speed Ball Milling

Authors

  • Solita Lam Albany State University, USA
  • Yvonne Puplampu Dove Albany State University, USA
  • Adrienne Morris Albany State University, USA
  • Ayunna Epps Albany State University, USA
  • Ghislain R Mandouma Albany State University, USA

DOI:

https://doi.org/10.31686/ijier.vol3.iss6.376

Keywords:

Solvent-free Reaction, Ullmann, Biarylation, Cross-coupling, High Speed, Ball Milling

Abstract

Solvent-free reaction using a high-speed ball milling technique has been applied to the classical Ullmann coupling reaction. Cross-coupling biarylation of several nitroaryl chlorides was achieved in good yields when performed in custom-made copper vials through continuous shaking without additional copper or solvent. Cross-coupling products were obtained almost pure and NMR-ready. These reactions were cleaner than solution phase coupling which require longer reaction time in high boiling solvents, and added catalysts as well as lengthy extraction and purification steps. Gram quantities of cross biaryl compounds have been synthesized with larger copper vials, a proof that this method can be used to reduce industrial waste and for sustainability.

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Author Biographies

  • Solita Lam, Albany State University, USA

    Department of Natural & Forensic Sciences

  • Yvonne Puplampu Dove, Albany State University, USA

    Department of Natural & Forensic Sciences

  • Adrienne Morris, Albany State University, USA

    Department of Natural & Forensic Sciences

  • Ayunna Epps, Albany State University, USA

    Department of Natural & Forensic Sciences

  • Ghislain R Mandouma, Albany State University, USA

    Department of Natural Sciences

References

(a) Y. Liu, S.S. Wang, W. Liu, Q.X., Wan, H.H. Wu, G.H. Gao, Curr. Org. Chem. 2009, 13, 1322-1346; (b) M. Moreno-Manas, R. Pleixats, Acc. Chem. Res. 2003, 36, 638-643.

(c) G. Evano, N. Blanchard, M. Toumi, Chem. Rev. 2008, 108, 3054-3131. DOI: https://doi.org/10.1021/cr8002505

N.T.S. Phan, M. Van Der Sluys, C.W. Jones, Adv. Synth. Catal. 2006, 348, 609-679. DOI: https://doi.org/10.1002/adsc.200505473

L.X. Yin, J. Liebscher, Chem. Rev. 2007, 107, 133-173. DOI: https://doi.org/10.1021/cr0505674

F.E. Ziegler, I. Chliwner, K.W. Fowler, S.J. Kanfer, S.J. Kuo, N.D. Sinha, J. Am. Chem. Soc. 1980, 102, 90. DOI: https://doi.org/10.1021/ja00522a058

For recent papers, see (a) F. Buttner, S. Bergemann, D. Guenard, R. Gust, G. Seitz, S. Thoret, Bioorg. Med. Chem. 2005, 13, 3497; (b) S.D. Broasy, M.D. Golden, J. Leonard, J.C. Muir, M. Maudet, tetrahedron Lett. 2007, 48, 4627; (c) P.S. Baran, J.M. Richter, D.W. Lin, Angew. Chem. Int. Ed. 2005, 44, 609. (d) G.A. Molander, K.M. George, L.G. Monovich, J. Org. Chem. 2003, 68, 9533.

F. Ullmann, J. Bielecki, Ber. Dtsch.Chem.Ges. 1901, 34, 2174, DOI: https://doi.org/10.1002/cber.190103402141

F. Ullmann, Ber. Dtsch.Chem.Ges. 1903, 36, 2382, DOI: https://doi.org/10.1002/cber.190303602174

I. Goldberg, Ber. Dtsch.Chem.Ges. 1906, 39, 1691. DOI: https://doi.org/10.1002/cber.19060390298

N. Miyaura, T. Yanagi, A. Suzuki, Synth. Commun. 1981, 11, 513. DOI: https://doi.org/10.1080/00397918108063618

J.K. Stille, Angew. Chem., Int. Ed. Engl. 1986, 98, 504.

E.-I. Negishi, F.-T. Luo, R. Frisbee, H. Matsushita, Heterocycles, 1982, 18, 117. DOI: https://doi.org/10.3987/S(B)-1982-01-0117

(a) F. Ullmann, Chem. Ber. 1903, 36, 2389; (b) T. Nelson, R.D. Crouch, Organic Reaction, 2004, Vol. 63, 265-555.

I. P. Beletskaya and A. V. Cheprakov, Coord. Chem. Rev., 2004, 248, 2337. DOI: https://doi.org/10.1016/j.ccr.2004.09.014

A. W. Thomas and S. V. Ley, Angew. Chem. Int. Ed. 2003, 42, 5400 – 5449. DOI: https://doi.org/10.1002/anie.200300594

J. Hassan, M. Sevignon, C. Gozzi, E. Shulz, M. Lemaire, Chem. Rev. 2002, 102, 1359 – 1469. DOI: https://doi.org/10.1021/cr000664r

G.R. Desiraju, Organic Solid State Chemistry, Elsevier, 1987, 6, 35

For history of mechanochemistry, see (a) Kaupp, G; CrystEngComm, 2011, 13, 3108-3121; (b) Concas, A; Lai, N; Pisu, M; Cao, G; Chem. Eng. Sci., 2006, 61, 3746-3760; (c) Stolle, A, Szuppa, T; Leonhardt, SES; Ondruschka, B; Chem. Soc. Rev., 2011, 40, 2317-2329; (d) Chem. Soc. Reviews, 2013, Vol.49, (e) L. Carlier, Tetrahedron Lett., 2011, 52, 4686-89.

Rodriguez, B; Bruckmann, A; Rantanen, T; Bolm, C: Adv. Synth. Catal., 2007, 349, 22132233; DOI: https://doi.org/10.1002/adsc.200700252

CAM Seidel, R. Kuhnemuth, Nature Nanotechnology, 2014, 9, 164-165; DOI: https://doi.org/10.1038/nnano.2014.46

Fulmer, DA; Shearouse, WC; Medonza, ST; Mack, J; Green Chem., 2009, 11, 1821-1825; DOI: https://doi.org/10.1039/b915669k

James, SL; Adams, CJ; Bolm, C; Braga, D; Collier, P; Friscic, T; Grepioni, F; Harris, KDM; Hyett, G; Jones, W; Krebs, A; Mack, J; Maini, L; Orpen, AG; Parkin, IP; Shearouse, WC; Steed, JW; Waddell, DC; Chem. Soc. Rev., 2012, 41(1), 413-447; DOI: https://doi.org/10.1039/C1CS15171A

P.T. Anastas and J.C. Warner, Green Chemistry: Theory and Practice, 1998 Oxford University Press.

A. de Meijere, F. Diederich, Metal-Catalyzed Cross-Coupling Reactions 2nd Ed. Vol.1 2004, Wiley-VCH. DOI: https://doi.org/10.1002/9783527619535

a) K. Tanaka and F. Toda, Chem. Rev., 2000, 100, 1025-1074. b) Y.-W. Dong, G.-W. Wang and L. Wang, Tetrahedron, 2008, 64, 10148-10154. DOI: https://doi.org/10.1021/cr940089p

(a) D. C. Waddell and J. Mack, Green Chem., 2009, 11, 79-82. (b) D. C. Waddell, I. Thiel, T. D. Clark, S. T. Marcum and J. Mack, Green Chem., 2010, 12, 209-211. (c) J. Mack, D. Fulmer, S. Stofel and N. Santos, Green. Chem., 2007, 9, 1041-1043.

a) B. M. Choudary, C. Sridhar, M. L. Kantam, G. T. Venkanna, B. Sreedhar, J. Am. Chem. Soc. 2005, 127, 9948; b) M. L. Kantam, G. T. Venkanna, C. Sridhar, K. B. Shiva Kumar, Tetrahedron Lett. 2006, 47, 3897.

S. V. Ley, A.W. Thomas, Angew. Chem. 2003, 115, 5558; Angew. Chem. Int. Ed. 2003, 42, 5400; b) K. Kunz, U. Scholz, D. Ganzer, Synlett 2003, 2428. I. P. Beletskaya, A. V. Cheprakov, Coord. Chem. Rev.2004, 248, 2337. R. Frlan, D. Kikelj, Synthesis 2006, 2271. M. Kienle, S. R. Dubakka, K. Brade, P. Knochel, Eur. J. Org. Chem. 2007, 4166. M. Carril, R. SanMartin, E. Dominguez, Chem. Soc. Rev. 2008, 37, 639.

J. W. Tye, Z.Weng, A. M. Johns, C. D. Incarvito, J. F. Hartwig, J. Am. Chem. Soc. 2008, 130, 9971. DOI: https://doi.org/10.1021/ja076668w

F. Monnier, M. Taillefer Angew. Chem. Int. Ed. 2009, 48, 6954 – 6971. DOI: https://doi.org/10.1002/anie.200804497

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Published

2015-06-01

How to Cite

Lam, S., Dove, Y. P., Morris, A., Epps, A., & Mandouma, G. R. (2015). Cross-Coupling Biarylation of Nitroaryl Chlorides Through High Speed Ball Milling. International Journal for Innovation Education and Research, 3(6), 12-35. https://doi.org/10.31686/ijier.vol3.iss6.376

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