Ni-Catalyzed Cross Coupling of Aryl Grignard Reagents with Aryl Halides in a Nonpolar Solvent and an Efficient Synthesis of Biaryls Under Neat Conditions

doi:10.1007/s40242-016-5261-0

Abstract

Abstract:

This study details Ni-catalyzed cross coupling of aryl Grignard reagents with aryl halides in toluene, a nonpolar solvent with a high boiling point. The reaction was applied for the synthesis of various biaryls in good yields without the introduction of a large steric ligand. The Kumada-Tamao-Corriu(KTC) reaction in toluene was then successfully modified to proceed under neat conditions for the efficient syntheses of symmetrical biaryls, particularly in large-scale preparations. Unactivated aryl chlorides show higher reactivity than aryl bromides, particularly under neat conditions. Mechanistic investigations suggest a radical procedure for the catalytic cycle, and the origin of the radical intermediates being aryl halides.

Key words: Cross-coupling, Nickel, Biaryl, Reaction mechanism, Neat condition

WU Qiang, JIN Rizhe, KANG Chuanqing, CHEN Wenhui, BIAN Zheng, MA Xiaoye, DING Jinying, GUO Haiquan, QIU Xuepeng, GAO Lianxun. Ni-Catalyzed Cross Coupling of Aryl Grignard Reagents with Aryl Halides in a Nonpolar Solvent and an Efficient Synthesis of Biaryls Under Neat Conditions[J]. Chemical Research in Chinese Universities, 2016, 32(1): 55-61.

References

[1] Riener K., Haslinger S., Raba A., Hogerl M. P., Cokojia M., Herrmann W. A., Kuhn F. E., Chem. Rev., 2014, 114(10), 5215
[2] Tasker S. Z., Standley E. A., Jamison T. F., Nature, 2014, 509, 299
[3] Kambe N., Iwasaki T., Terao J., Chem. Soc. Rev., 2011, 40(10), 4937
[4] Knappke C. E. I., Jacobi von Wangelin A., Chem. Soc. Rev., 2011, 40(10), 4948
[5] Cahiez G., Moyeux A., Chem. Rev., 2010, 110(3), 1435
[6] Rudolph A., Lautens M., Angew. Chem. Int. Ed., 2009, 48(15), 2656
[7] Wu X. M., Wang Y., Guo S. R., Chem. Res. Chinese Universities, 2010, 26(2), 331
[8] Wang Y. L., Wu Y. J., Chem. Res. Chinese Universities, 2000, 16(2), 131
[9] Jana R., Pathak T. P., Sigman M. S., Chem. Rev., 2011, 111(3), 1417
[10] Rosen B. M., Quasdorf K. W., Wilson D. A., Zhang N., Resmerita A. M., Garg N. K., Percec V., Chem. Rev., 2011, 111(3), 1346
[11] Tucker C. E., de Vries J. G., Top. Catal., 2002, 19(1), 111
[12] Hu X. L., Chem. Sci., 2011, 2(10), 1867
[13] Lipschutz M. I., Yang X., Chatterjee R., Tilley T. D., J. Am. Chem. Soc., 2013, 135(41), 15298
[14] Tennyson A. G., Lynch V. M., Bielawski C. W., J. Am. Chem. Soc., 2010, 132(27), 9420
[15] Klein A., Budnikova Y. H. O., Sinyashin G., J. Organomet. Chem., 2007, 692(15), 3156
[16] Jones G. D., Martin J. L., McFarland C., Allen O. R., Hall R. E., Haley A. D., Jacob Brandon R., Konovalova T., Desrochers, P. J., Pulay, P., Vicic D. A., J. Am. Chem. Soc., 2006, 128(40), 13175
[17] Jin Z., Li Y. J., Ma Y. Q., Qiu L. L., Fang J. X., Chem. Eur. J., 2012, 18(2), 446
[18] Guo W. J., Wang Z. X., J. Org. Chem., 2013, 78(3), 1054
[19] Sun Y., Li X., Sun H., Dalton Trans., 2014, 43(25), 9410
[20] Daifuku S. L., Al-Afyouni M. H., Snyder B. E., Kneebone R. J. L., J. Am. Chem. Soc., 2014, 136(25), 9132
[21] Xu Y. C., Zhang J., Sun H. M., Shen Q., Zhang Y., Dalton Trans., 2013, 42(23), 8437
[22] Iglesias M. J., Prieto A., Nicasio M. C., Org. Lett., 2012, 14(17), 4318
[23] Monnereau L., Sémeril D., Matt D., Chem. Commun., 2011, 47(23), 6626
[24] Vechorkin O., Proust V., Hu X. L., J. Am. Chem. Soc., 2009, 131(28), 9756
[25] Ackermann L., Born R., Spatz J. H., Meyer D., Angew. Chem. Int. Ed., 2005, 44(44), 7216
[26] Guisán-Ceinos M., Soler-Yanes R., Collado-Sanz D., Phapale V. B., Buñuel E., Cárdenas D. J., Chem. Eur. J., 2013, 19(26), 8405
[27] Terao J., Watanabe H., Ikumi A., Kuniyasu H., Kambe N., J. Am. Chem. Soc., 2002, 124(16), 4222
[28] Sun Y., Li, X., Sun H., Inorg. Chimica Acta, 2014, 415, 95
[29] Li G. Y., Angew. Chem. Int. Ed., 2001, 40(8), 1513
[30] Ren G., Cui X., Wu Y., Eur. J. Org. Chem., 2010, 2010(12), 2372
[31] Liu N., Wang Z. X., J. Org. Chem., 2011, 76(24), 10031
[32] Korn T. J., Schade M. A., Cheemala M. N., Wirth S., Guevara S. A., Cahiez G., Knochel P., Synthesis, 2006,(4), 3547
[33] Inamoto K., Kuroda J., Sakamoto T., Hiroya K., Synthesis, 2007, (5), 2853
[34] Wang Z. X., Wang L., Chem. Commun., 2007, 43(23), 2423
[35] Hatakeyama T., Nakamura M., J. Am. Chem. Soc., 2007, 129(32), 9844
[36] Lipschutz M. I., Don Tilley T., Angew. Chem. Int. Ed., 2014, 53(28), 7290
[37] Zheng B., Tang F., Luo J., Schultz J. W., Rath N. P., Mirica L. M., J. Am. Chem. Soc., 2014, 136(17), 6499
[38] Zhou Z., Xue W., J. Organomet. Chem., 2009, 694(5), 599
[39] Nagano T., Hayashi T., Org. Lett., 2005, 7(3), 491
[40] Amay T., Suzuki R., Hirao T., Chem. Eur. J., 2014, 20(3), 653
[41] Yuan, C., Fang, Q., RSC Adv., 2012, 2(21), 8055
[42] Liaw D.., Wang K. L., Huang Y. C., Lee K. R., Lai J. Y., Ha C. S., Prog. Polym. Sci., 2012, 37(7), 907
[43] Pramanik S., Hu Z., Zhang X., Zheng C., Kelly S., Li J., Chem. Eur. J., 2013, 19(47), 15964
[44] Falaise C., Volkringer C., Vigier, J. F., Henry N., Beaurain A., Loiseau T., Chem. Eur. J., 2013, 19(17), 5324
[45] Gao C., Li G., Sun X., A Method for Separation and Purification of the Tetramethyl-biphenyl Mixture of Isomers, CN 201410476886, 2014
[46] Liu W., Lei A., Tetrahedron Lett., 2007, 49(4), 610
[47] Tamio H., Jiro N., Method for Producing a Biphenyl Derivative, EP2075241, 2009
[48] Mukhopadhyay S., Rothenberg G., Wiener H., Sasson Y., Tetrahedron, 1999, 55(51), 14763
[49] Mukhopadhyay S., Rothenberg G., Wiener H., Sasson Y., J. Chem. Soc., Perkin Trans., 1999, 2(11), 2481
[50] Breitenfeld J., Ruiz J., Wodrich M. D., Hu X. L., J. Am. Chem. Soc., 2013, 135(32), 12004
[51] Joshi-Pangu A., Wang C. Y., Biscoe M. R., J. Am. Chem. Soc., 2011, 133(22), 8478
[52] Punji B., Song W., Shevchenko G. A., Ackermann L., Chem. Eur. J., 2013, 19(32), 10605
[53] Garcia P. M. P., Franco T. D., Orsino A., Ren P., Hu X. L., Org. Lett., 2012, 14(16), 4286
[54] Feng Z., Chen F., Zhang X., Org. Lett., 2012, 14(7), 1938
[55] Kuzmina O. M., Steib A. K., Markiewicz J. T., Flubacher D., Knochel P., Angew. Chem. Int. Ed., 2013, 52(18), 4945