Remote C-H Bond Functionalizations. Группа авторов

of meta‐C–H functionalization assisted by directing templates.

      Abbreviations

      AcacetylAlaL‐alanineArarylBoctert‐butyloxycarbonylBnbenzylBubutylCANceric ammonium nitratecat.catalyticCMDconcerted metalation–deprotonationDCE1,2‐dichloroethaneDGdirecting templateDIH1,3‐diiodo‐5,5‐dimethylhydantoinDMFN,N‐dimethylformamideDMPU1,3‐dimethyl‐3,4,5,6‐tetrahydro‐2(1H)‐pyrimidinoneequivequivalentEDGelectron‐donating templateEWGelectron‐withdrawing templateGlyglycineHFIPhexafluoroisopropanolKIEkinetic isotope effectLligandLDAlithium diisopropylamidemmetaMemethylMPAAmono‐N‐protected amino acidNMPN‐methylpyrrolidinoneoorthopparaPhphenylPheL‐phenylalaninePinpinacolPivpivaloylPrpropylTBAtetrabutylammoniumTFAtrifluoroacetic acidTBAPF6tetrabutylammonium hexafluorophosphateTFEtrifluoroethanolTHFtetrahydrofuranXPhos2,4′,6′‐diisopropyl‐1,1′‐biphenyl‐2‐yldicyclohexylphosphine

References

      1 1 Truong, T. and Daugulis, O. (2012). Angew. Chem. Int. Ed. 51: 11677.

      2 2 Julia‐Hernandez, F., Simonetti, M., and Larrosa, I. (2013). Angew. Chem. Int. Ed. 52: 11458.

      3 3 Ackermann, L. and Li, J. (2015). Nat. Chem. 7: 686.

      4 4 Frost, C.G. and Paterson, A.J. (2015). ACS Cent. Sci. 1: 418.

      5 5 Li, J., De Sarkar, S., and Ackermann, L. (2016). Top. Organomet. Chem. 55: 217.

      6 6 Yang, J. (2015). Org. Biomol. Chem. 13: 1930.

      7 7 Chattopadhyay, B. and Bisht, R. (2016). Synlett 27: 2043.

      8 8 Dey, A., Agasti, S., and Maiti, D. (2016). Org. Biomol. Chem. 14: 5440.

      9 9 Ghosh, M. and De Sarkar, S. (2018). Asian J. Org. Chem. 7: 1236.

      10 10 Dey, A., Sinha, S.K., Achar, T.K., and Maiti, D. (2019). Angew. Chem. Int. Ed. 58: 10820.

      11 11 Leow, D., Li, G., Mei, T.S., and Yu, J.‐Q. (2012). Nature 486: 518.

      12 12 Zhang, Z., Tanaka, K., and Yu, J.‐Q. (2017). Nature 543: 538.

      13 13 Achar, T.K., Ramakrishna, K., Pal, T. et al. (2018). Chem. Eur. J. 24: 17906.

      14 14 Modak, A., Mondal, A., Watile, R. et al. (2016). Chem. Commun. 52: 13916.

      15 15 Li, S., Wang, H., Weng, Y., and Li, G. (2019). Angew. Chem. Int. Ed. https://doi.org/10.1002/anie.201910691.

      16 16 Xu, H.‐J., Lu, Y., Farmer, M.E. et al. (2017). J. Am. Chem. Soc. 139: 2200.

      17 17 Xu, H.‐J., Kang, Y.‐S., Shi, H. et al. (2019). J. Am. Chem. Soc. 141: 76.

      18 18 Wan, L., Dastbaravardeh, N., Li, G., and Yu, J.‐Q. (2013). J. Am. Chem. Soc. 135: 18056.

      19 19 Xu, H., Liu, M., Li, L.J. et al. (2019). Org. Lett. 21: 4887.

      20 20 Bera, M., Modak, A., Patra, T. et al. (2014). Org. Lett. 16: 5760.

      21 21 Deng, Y. and Yu, J.‐Q. (2015). Angew. Chem. Int. Ed. 54: 888.

      22 22 Bera, M., Agasti, S., Chowdhury, R. et al. (2017). Angew. Chem. Int. Ed. 56: 5272.

      23 23 Jin, Z., Chu, L., Chen, Y.‐Q., and Yu, J.‐Q. (2018). Org. Lett. 20: 425.

      24 24 Brochetta, M., Borsari, T., Bag, S. et al. (2019). Chem. Eur. J. 25: 10323.

      25 25 Jiao, B., Peng, Z., Dai, Z.‐H. et al. (2019). Eur. J. Org. Chem. 2019: 3195.

      26 26 Bag, S., Petzold, M., Sur, A. et al. (2019). Chem. Eur. J. 25: 9433.

      27 27 Achar, T.K., Zhang, X., Mondal, R. et al. (2019). Angew. Chem. Int. Ed. 58: 10353.

      28 28 Li, S., Cai, L., Ji, H. et al. (2016). Nat. Commun. 7: 10443.

      29 29 Fang, L., Saint‐Denis, T.G., Taylor, B.L.H. et al. (2017). J. Am. Chem. Soc. 139: 10702.

      30 30 Phipps, R.J. and Gaunt, M.J. (2009). Science 323: 1593.

      31 31 Tang, R.‐Y., Li, G., and Yu, J.‐Q. (2014). Nature 507: 215.

      32 32 Yang, L., Fu, L., and Li, G. (2017). Adv. Synth. Catal. 359: 2235.

      33 33 Wang, B., Zhou, Y., Xu, N. et al. (2019). Org. Lett. 21: 1885.

      34 34 Li, S., Ji, H., Cai, L., and Li, G. (2015). Chem. Sci. 6: 5595.

      35 35 Yang, G., Lindovska, P., Zhu, D. et al. (2014). J. Am. Chem. Soc. 136: 10807.

      36 36 Dutta, U., Modak, A., Bhaskararao, B. et al. (2017). ACS Catal. 7: 3162.

      37 37 Yang, G., Zhu, D., Wang, P. et al. (2018). Chem. Eur. J. 24: 3434.

      38 38 Bera, M., Maji, A., Sahoo, S.K., and Maiti, D. (2015). Angew. Chem. Int. Ed. 54: 8515.

      39 39 Bag, S., Jayarajan, R., Mondal, R., and Maiti, D. (2017). Angew. Chem. Int. Ed. 56: 3182.

      40 40 Maji, A., Bhaskararao, B., Singha, S. et al. (2016). Chem. Sci. 7: 3147.

      41 41 Bag, S., Jayarajan, R., Dutta, U. et al. (2017). Angew. Chem. Int. Ed. 56: 12538.

      42 42 Modak, A., Patra, T., Chowdhury, R. et al. (2017). Organometallics 36: 2418.

      43 43 Dai, H.‐X., Li, G., Zhang, X.‐G. et al. (2013). J. Am. Chem. Soc. 135: 7567.

      44 44 Mi, R.‐J., Sun, J., Kuhn, F.E. et al. (2017). Chem. Commun. 53: 13209.

      45 45 Mi, R.‐J., Sun, Y.‐Z., Wang, J.Y. et al. (2018). Org. Lett. 20: 5126.

      46 46 Xu, J., Chen, J., Gao, F. et al. (2019). J. Am. Chem. Soc. 141: 1903.

      47 47 Maity, S., Hoque, E., Dhawa, U., and Maiti, D. (2016). Chem. Commun. 52: 14003.

      48 48 Lee, S., Lee, H., and Tan, K.L. (2013). J. Am. Chem. Soc. 135: 18778.

      49 49 Chu, L., Shang, M., Tanaka, K. et al. (2015). ACS Cent. Sci. 1: 394.

      50 50 Zhang, L., Zhao, C., Liu, Y. et al. (2017). Angew. Chem. Int. Ed. 56: 12245.

      51 51 Jayarajan, R., Das, J., Bag, S. et al. (2018). Angew. Chem. Int. Ed. 57: 7659.

      52 52 Fang, S., Wang, X., Yin, F. et al. (2019). Org. Lett. 21: 1841.

      53 53 Patra, T., Watile, R., Agasti, S. et al. (2016). Chem. Commun. 52: 2027.

      54 54 Bera, M., Sahoo, S.K., and Maiti, D. (2016). ACS Catal. 6: 3575.

      55 55 Yang, Y.‐F., Cheng, G.J., Liu, P. et al. (2014). J. Am. Chem. Soc. 136: 344.

      56 56 Cheng, G.‐J., Yang, Y.‐F., Liu, P. et al. (2014). J. Am. Chem. Soc. 136: 894.