Citation: Huang Yuanqiong, Lv Xueli, Song Hongjian, Liu Yuxiu, Wang Qingmin. Rh(III)-catalyzed C8 arylation of quinoline N-oxides with arylboronic acids[J]. Chinese Chemical Letters, ;2020, 31(6): 1572-1575. doi: 10.1016/j.cclet.2019.11.028 shu

Rh(III)-catalyzed C8 arylation of quinoline N-oxides with arylboronic acids

    * Corresponding authors at: State Key Laboratory of Elemento-Organic Chemistry Research Institute of Elemento-Organic Chemistry College of Chemistry Nankai University Tianjin 300071 China.
    E-mail addresses: songhongjian@nankai.edu.cn (H. Song) wangqm@nankai.edu.cn (Q. Wang).
  • Received Date: 14 September 2019
    Revised Date: 16 November 2019
    Accepted Date: 16 November 2019
    Available Online: 1 June 2020

Figures(6)

  • Herein, we report the first RhIII-catalyzed regioselective C8 arylation of quinoline N-oxides with commercially available arylboronic acids as coupling partners. This procedure is simple, and the reaction shows perfect regioselectivity, a broad substrate scope, and isolated yields of up to 92%. We demonstrate the utility of the reaction by using it for late-stage functionalization of a fungicide.
  • 加载中
    1. [1]

      (a) Z. Wu, Z. Zhen, J.H. Jiang, G.L. Shen, R.Q. Yu, J. Am. Chem. Soc. 131 (2009) 12325-12332;
      (b) W.A. Denny, B.F. Cain, G.J. Atwell, et al., J. Med. Chem. 25 (1982) 276-315;
      (c) A.B. Burgin, O.T. Magnusson, J. Singh, et al., Curr. Med. Chem. 18 (2011) 1488-1508.

    2. [2]

      (a) J.vanGeer, J.A.J.Hanraads, R.A.Lupton, etal., J.Sci.Commun.163 (2010)51-59;
      (b) G. Höfle, B. Kunze, J. Nat. Prod. 71 (2008) 1843-1849;
      (c) J.P. Michael, Nat. Prod. Rep. 24 (2007) 223-246;
      (d) Q.A. Khan, J. Lu, S.M. Hecht, J. Nat. Prod. 72 (2009) 438-442.

    3. [3]

      (a) J.I. Kim, I.S. Shin, H. Kim, J.K. Lee, J. Am. Chem. Soc. 127 (2005) 1614-1615;
      (b) G. Yang, Y. Si, Z. Su, Org. Biomol. Chem. 10 (2012) 8418-8425.

    4. [4]

      (a) M. Nakajima, M. Saito, M. Shiro, S.I. Hashimoto, J. Am. Chem. Soc.120 (1998) 6419-6420;
      (b) S.E. Denmark, Y. Fan, J. Am. Chem. Soc. 124 (2002) 4233-4235;
      (c) M.S. Taylor, E.N. Jacobsen, PNAS 101 (2004) 5368-5373;
      (d) C. Verrier, P. Melchiorre, Chem. Sci. 6 (2015) 4242-4246;
      (e) M. Moliterno, R. Cari, A.A. Antenucci, et al., Angew. Chem. Int. Ed. 55 (2016) 6525-6529.

    5. [5]

      (a) A.E. Shilov, G.B. Shul0pin, Chem. Rev. 97 (1997) 2879-2932;
      (b) R.G. Bergman, Nature 446 (2007) 391-393;
      (c) O. Daugulis, H.Q. Do, D. Shabashov, Acc. Chem. Res. 42 (2009) 1074-1086;
      (d) D.A. Colby, R.G. Bergman, J.A. Ellman, Chem. Rev. 110 (2010) 624-655;
      (e) L. Ackermann, Chem. Rev. 111 (2011) 1315-1345;
      (f) K.M. Engle, T.S. Mei, M. Wasa, J.Q. Yu, Acc. Chem. Res. 45 (2011) 788-802;
      (g) B.J. Li, Z.J. Shi, Chem. Soc. Rev. 41 (2012) 5588-5598;
      (h) J. Yamaguchi, A.D. Yamaguchi, K. Itami, Angew. Chem. Int. Ed. 51 (2012) 8960-9009;
      (i) G.Y. Song, F. Wang, X.W. Li, Chem. Soc. Rev. 41 (2012) 3651-3678;
      (j) J. Wencel-Delord, F. Glorius, Nat. Chem. 5 (2013) 369-375;
      (k) J.R. Hummel, J.A. Boerth, J.A. Ellman, Chem. Rev. 117 (2017) 9163-9227;
      (l) J. Kim, K. Shin, S. Jin, D. Kim, S. Chang, J. Am. Chem. Soc.141 (2019) 4137-4146.

    6. [6]

      (a) J. Ryu, S.H. Cho, S. Chang, Angew. Chem. Int. Ed. 51 (2012) 3677-3681;
      (b) B. Yao, R.J. Song, Y. Liu, et al., Adv. Synth. Catal. 354 (2012) 1890-1896;
      (c) Z.Y. Wu, C. Pi, X.L. Cui, J. Bai, Y.J. Wu, Adv. Synth. Catal. 355 (2013) 1971-1976;
      (d) B. Xiao, Z.J. Liu, L. Liu, Y. Fu, J. Am. Chem. Soc. 135 (2013) 616-619;
      (e) O.V. Larionov, D. Stephens, A. Mfuh, G. Chavez, Org. Lett.16 (2014) 864-869;
      (f) A.K. Jha, N. Jain, Chem. Commun. 52 (2016) 1831-1834;
      (g) S.J. Yu, H.L. Sang, S.Z. Ge, Angew. Chem. Int. Ed. 56 (2017) 15896-15900.

    7. [7]

      (a) K.S.Kanyiva, Y.Nakao, T.Hiyama, Angew.Chem.Int.Ed.46 (2007)8872-8874;
      (b) S.H. Cho, S.J. Hwang, S. Chang, J. Am. Chem. Soc. 130 (2008) 9254-9256;
      (c) J.L. Wu, X.L. Cui, L.M. Chen, G.J. Jiang, Y.J. Wu, J. Am. Chem. Soc. 131 (2009) 13888-13889;
      (d) F. Roudesly, L.F. Veiros, J. Oble, G. Poli, Org. Lett. 20 (2018) 2346-2350.

    8. [8]

      (a) L.C. Campeau, D.R. Stuart, J.P. Leclerc, et al., J. Am. Chem. Soc. 131 (2009) 3291-3306;
      (b) D.B. Zhao, W.H. Wang, F. Yang, et al., Angew. Chem. Int. Ed. 48 (2009) 3296-3300;
      (c) P.H. Xi, F. Yang, S. Qin, et al., J. Am. Chem. Soc. 132 (2010) 1822-1824;
      (d) H. Wang, Y. Pei, J. Bai, et al., RSC Adv. 4 (2014) 26244-26246;
      (e) X.P. Chen, X.L. Cui, F.F. Yang, Y.J. Wu, Org. Lett. 17 (2015) 1445-1448.

    9. [9]

      (a) Z.Y. Wu, H.Y. Song, X.L. Cui, et al., Org. Lett. 15 (2013) 1270-1273;
      (b) B.N. Du, P. Qian, Y. Wang, et al., Org. Lett. 18 (2016) 4144-4147.

    10. [10]

      X. Chen, C.W. Zhu, X.L. Cui, Y.J. Wu, Chem. Commun. 49(2013) 6900-6902.  doi: 10.1039/c3cc43947j

    11. [11]

      H. Wang, X.L. Cui, Y. Pei, et al., Chem. Commun. 50(2014) 14409-14411.  doi: 10.1039/C4CC07060G

    12. [12]

      (a) G. Li, C.Q. Jia, K. Sun, Org. Lett. 15 (2013) 5198-5201;
      (b) C.W. Zhu, M.L. Yi, D.H. Wei, et al., Org. Lett. 16 (2014) 1840-1843;
      (c) W.L. Xie, J.H. Yoon, S. Chang, J. Am. Chem. Soc. 138 (2016) 12605-12614.

    13. [13]

      B. Yao, C.L. Deng, Y. Liu, et al., Chem. Commun. 51(2015) 4097-4100.  doi: 10.1039/C4CC10140E

    14. [14]

      (a) J. Kwak, M. Kim, S. Chang, J. Am. Chem. Soc. 133 (2011) 3780-3783;
      (b) H.Hwang, J.Kim, J.Jeong, S.Chang, J.Am.Chem.Soc.136 (2014)10770-10776;
      (c) X.T. Zhang, Z.S. Qi, X.W. Li, Angew. Chem. Int. Ed. 53 (2014) 10794-10798;
      (d) J. Jeong, P. Patel, H. Hwang, S. Chang, Org. Lett. 16 (2014) 4598-4601;
      (e) T. Shibata, Y. Matsuo, Adv. Synth. Catal. 356 (2014) 1516-1520;
      (f) U. Sharma, Y. Park, S. Chang, J. Org. Chem. 79 (2014) 9899-9906;
      (g) S. Konishi, S. Kawamorita, T. Iwai, et al., Chem. Asian J. 9 (2014) 434-438;
      (h) Y. Park, K.T. Park, J.G. Kim, S. Chang, J. Am. Chem. Soc.137 (2015) 4534-4542;
      (i) K. Shin, S.W. Park, S. Chang, J. Am. Chem. Soc. 137 (2015) 8584-8592;
      (j) D.E. Stephens, J. Lakey-Beitia, A.C. Atesin, et al., ACS Catal. 5 (2015) 167-175;
      (k) D.E. Stephens, J. Lakey-Beitia, G. Chavez, et al., Chem. Commun. 51 (2015) 9507-9510;
      (l) D. Gwon, H. Hwang, H.K. Kim, S.R. Marder, S. Chang, Chem. Eur. J. 21 (2015) 17200-17204;
      (m)R.Sharma, R.Kumar, I.Kumar, U.Sharma, Eur.J.Org.Chem.2015 (2015)7519-7528;
      (n) X.H. Hu, X.F. Yang, T.P. Loh, ACS Catal. 6 (2016) 5930-5934;
      (o) N. Barsu, M. Sen, J.R. Premkumar, B. Sundararaju, Chem. Commun. 52 (2016) 1338-1341;
      (p) X.P. Chen, X.L. Cui, Y. Wu, J. Org. Lett. 18 (2016) 2411-2414;
      (q) X.P. Chen, X.L. Cui, Y.J. Wu, Org. Lett. 18 (2016) 3722-3725;
      (r) D. Kalsi, R.A. Laskar, N. Barsu, J.R. Premkumar, B. Sundararaju, Org. Lett. 18 (2016) 4198-4201;
      (s) R. Sharma, I. Kumar, R. Kumar, U. Sharma, Adv. Synth. Catal. 359 (2017) 3022-3028;
      (t) B. Wang, C.P. Li, H. Liu, Adv. Synth. Catal. 359 (2017) 3029-3034;
      (u) C. You, C. Pi, Y.J. Wu, X.L. Cui, Adv. Synth. Catal. 360 (2018) 4068-4072;
      (v) R. Sharma, R. Kumar, U. Sharma, J. Org. Chem. 84 (2019) 2786-2797;
      (w) B. Ghosh, A. Biswas, S. Chakraborty, R. Samanta, Chem. Asian J. 13 (2018) 2388-2392;
      (x) C. You, T.T. Yuan, Y.Z. Huang, et al., Org. Biomol. Chem.16 (2018) 4728-4733.

    15. [15]

      (a) J. Kim, S. Kim, D. Kim, S. Chang, J. Org. Chem. 84 (2019) 13150-13158;
      (b) Z.H. Zhang, C. Pi, H. Tong, X.L. Cui, Y.J. Wu, Org. Lett. 19 (2017) 440-443.

    16. [16]

      K. Konno, K. Hashimoto, H. Shirahama, T. Matsumoto, Heterocycles 24(1986) 2169-2172.  doi: 10.3987/R-1986-08-2169

    17. [17]

      D. Wenkert, R.B. Woodward, J. Org. Chem. 48(1983) 283-289.  doi: 10.1021/jo00151a001

    18. [18]

      X.M. Wang, D.G. Yu, F. Glorius, Angew. Chem. Int. Ed. 54(2015) 10280-10283.  doi: 10.1002/anie.201503888

  • 加载中
    1. [1]

      Yuan-Ye JiangHai-Zhu YuJing Shi . Mechanistic study on the regioselectivity of Co-catalyzed hydroacylation of 1,3-dienes. Chinese Chemical Letters, 2015, 26(1): 58-62. doi: 10.1016/j.cclet.2014.10.021

    2. [2]

      Jian-Jun LiXing-Xing Gui . L-ProT catalyzed highly regioselective N-alkoxyalkylation of purine rings with vinyl ethers. Chinese Chemical Letters, 2014, 25(10): 1341-1345. doi: 10.1016/j.cclet.2014.04.023

    3. [3]

      Min JiangHai-Jun YangYong LiZhi-Ying JiaHua Fu . Metal-free synthesis of substituted phenols from arylboronic acids in water at room temperature. Chinese Chemical Letters, 2014, 25(05): 715-719. doi: 10.1016/j.cclet.2014.03.018

    4. [4]

      Dan Xu Zhi Hua Liu Wei Jun Tang Jun Mo Li Jin Xu . Palladium-catalyzed highly regioselective Heck reaction of aryl nonaflates with electron-rich olefins. Chinese Chemical Letters, 2008, 19(9): 1017-1020. doi: 10.1016/j.cclet.2008.06.004

    5. [5]

      Xing LiZhi-Qin SunHong-Hong ChangWen-Long Wei . Highly efficient regioselective ring openings of N-tosylaziridines to haloamines using ferric (Ⅲ) halides. Chinese Chemical Letters, 2014, 25(8): 1174-1178. doi: 10.1016/j.cclet.2014.03.033

    6. [6]

      Xiao GenhuaMin HaoZheng ZhileiDeng GuoboLiang Yun . Copper-catalyzed three-component reaction of imidazo[1, 2-a]pyridine with elemental sulfur and arylboronic acid to produce sulfenylimidazo[1, 2-a]pyridines. Chinese Chemical Letters, 2018, 29(9): 1363-1366. doi: 10.1016/j.cclet.2017.12.013

    7. [7]

      Huan Sheng Chen Xia Ping Ma Zhi Ming Li Quan Rui Wang Feng Gang Tao . An effective synthesis of β-aryl substituted isotetronic acids via Suzuki coupling. Chinese Chemical Letters, 2008, 19(11): 1309-1311. doi: 10.1016/j.cclet.2008.09.016

    8. [8]

      Chong-Qing WangXin ChenJun-Hang JiangHui TangKong-Kai ZhuYou-Jun ZhouCan-Hui ZhengJu Zhu . Acidic rearrangement of benzyl group in flavone benzyl ethers and its regioselectivity. Chinese Chemical Letters, 2015, 26(6): 793-796. doi: 10.1016/j.cclet.2015.03.035

    9. [9]

      Yang LiuZhong-Zhi YangDong-Xia Zhao . Rationalization of regioselectivity of electrophilic substitution reaction for cyclic compounds in terms of Dpb values. Chinese Chemical Letters, 2015, 26(5): 553-556. doi: 10.1016/j.cclet.2014.12.013

    10. [10]

      Peng ShaSong Yan-XiHe Jun-YiTang Shan-ShanTan Jia-XiCao ZhongLin Ying-WuHe Wei-Min . TsCl-promoted sulfonylation of quinoline N-oxides with sodium sulfinates in water. Chinese Chemical Letters, 2019, 30(12): 2287-2290. doi: 10.1016/j.cclet.2019.08.002

    11. [11]

      Han Xiang-LeiLin Peng-PengLi Qingjiang . Recent advances of allenes in the first-row transition metals catalyzed C—H activation reactions. Chinese Chemical Letters, 2019, 30(8): 1495-1502. doi: 10.1016/j.cclet.2019.04.027

    12. [12]

      Yong Mei Xiao Pu Mao Zhen Zhao Liang Ru Yang Xian Fu Lin . Regioselective enzymatic acylation of troxerutin in nonaqueous medium. Chinese Chemical Letters, 2010, 21(1): 59-62. doi: 10.1016/j.cclet.2009.08.017

    13. [13]

      Ali Reza Kiasat Roya Mirzajani Haji Shalbaf Tahereh Tabatabaei . Nuclephilic ring opening of epoxides promoted by multi-site phase-transfer catalyst:An efficient and eco-friendly route to synthesis of b-hydroxy-thiocyanate. Chinese Chemical Letters, 2009, 20(9): 1026-1029. doi: 10.1016/j.cclet.2009.04.015

    14. [14]

      Xin Yong Liu Ren Zhang Yan Nian Gen Chen Wen Fang Xu . Regioselective synthesis and anti-HIV activity of the novel 2-and 4-substituted pyrazolo[4,5-e] [1,2,4]thiadiazines. Chinese Chemical Letters, 2007, 18(2): 137-140. doi: 10.1016/j.cclet.2006.12.006

    15. [15]

      Qi WU Jian Yue FENG Chen Guo FENG De Shui LU Xian Fu LIN . Enzymatic regioselective symthesis of vinthesis of vinyl lactose ester and its chemical polymerization. Chinese Chemical Letters, 2002, 13(5): 416-419.

    16. [16]

      Yang JianlinZhang MingWang PengLiu WenjuanRuwei Shen . 2-Amino homopropargyl alcohols from the highly regioselective Ag2CO3-catalyzed nucleophilic openings of alkynyl epoxides by amines. Chinese Chemical Letters, 2018, 29(3): 524-526. doi: 10.1016/j.cclet.2017.09.001

    17. [17]

      Mao RunvzeSun LifengWang Yong-ShiZhou Min-MinXiong De-CaiLi QinYe Xin-ShanN-9 Alkylation of purines via light-promoted and metal-free radical relay. Chinese Chemical Letters, 2018, 29(1): 61-64. doi: 10.1016/j.cclet.2017.08.005

    18. [18]

      Dao-Qing Dong Li-Xia Li Guang-Hui Li Qi Deng Zu-Li Wang Shu Long . Visible-light-induced deoxygenative C2-sulfonylation of quinoline N-oxides with sulfinic acids for the synthesis of 2-sulfonylquinoline via radical reactions. Chinese Journal of Catalysis, 2019, 40(10): 1494-1498. doi: S1872-2067(19)63420-0

    19. [19]

      Cao ZhongZhu QinLin Ying-WuHe Wei-Min . The concept of dual roles design in clean organic preparation. Chinese Chemical Letters, 2019, 30(12): 2132-2138. doi: 10.1016/j.cclet.2019.09.041

Metrics
  • PDF Downloads(2)
  • Abstract views(125)
  • HTML views(1)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return