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

高等学校化学研究 ›› 2016, Vol. 32 ›› Issue (1): 55-61.doi: 10.1007/s40242-016-5261-0

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

WU Qiang^1,2, JIN Rizhe¹, KANG Chuanqing¹, CHEN Wenhui¹, BIAN Zheng¹, MA Xiaoye¹, DING Jinying¹, GUO Haiquan¹, QIU Xuepeng¹, GAO Lianxun¹

1. State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China;
2. University of Chinese Academy of Sciences, Beijing 100864, P. R. China

收稿日期:2015-07-06 修回日期:2015-08-24 出版日期:2016-02-01 发布日期:2015-10-26
通讯作者: KANG Chuanqing, GAO Lianxun E-mail:kangcq@ciac.ac.cn;lxgao@ciac.ac.cn
基金资助:
Supported by the National Basic Research Program of China(No.2014CB643603) and the Jilin Technology R&D Program, China(No.20140203003GX).

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

WU Qiang^1,2, JIN Rizhe¹, KANG Chuanqing¹, CHEN Wenhui¹, BIAN Zheng¹, MA Xiaoye¹, DING Jinying¹, GUO Haiquan¹, QIU Xuepeng¹, GAO Lianxun¹

1. State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China;
2. University of Chinese Academy of Sciences, Beijing 100864, P. R. China

Received:2015-07-06 Revised:2015-08-24 Online:2016-02-01 Published:2015-10-26
Contact: KANG Chuanqing, GAO Lianxun E-mail:kangcq@ciac.ac.cn;lxgao@ciac.ac.cn
Supported by:
Supported by the National Basic Research Program of China(No.2014CB643603) and the Jilin Technology R&D Program, China(No.20140203003GX).

摘要/Abstract

摘要：

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.

关键词: Cross-coupling, Nickel, Biaryl, Reaction mechanism, Neat condition

Abstract:

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]. 高等学校化学研究, 2016, 32(1): 55-61.

参考文献

[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

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

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

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