Metal-free directed C-H borylation of 2-(N-methylanilino)-5-fluoropyridines and 2-benzyl-5-fluoropyridines
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* Corresponding authors.
E-mail addresses: 201701033@bucm.edu.cn (T. Ma), jyf@ecust.edu.cn(Y. Ji).
Citation: Gaorong Wu, Xiaobo Xu, Shuai Wang, Lu Chen, Binghan Pang, Tao Ma, Yafei Ji. Metal-free directed C-H borylation of 2-(N-methylanilino)-5-fluoropyridines and 2-benzyl-5-fluoropyridines[J]. Chinese Chemical Letters, ;2022, 33(4): 2005-2008. doi: 10.1016/j.cclet.2021.09.081
M.Y. Liu, S.B. Hong, W. Zhang, W. Deng, Chin. Chem. Lett. 26(2015) 373-376.
doi: 10.1016/j.cclet.2014.12.004
A.K. Cook, S.D. Schimler, A.J. Matzger, M.S. Sanford, Science 351(2016) 1421-1424.
doi: 10.1126/science.aad9289
T.J. Gong, Y.Y. Jiang, Y. Fu, Chin. Chem. Lett. 25(2014) 397-400.
doi: 10.1016/j.cclet.2014.01.006
M.E. Hoque, M.M.M. Hassan, B. Chattopadhyay, J. Am. Chem. Soc. 143(2021) 5022-5037.
doi: 10.1021/jacs.0c13415
M.R. Smith, R. Bisht, C. Haldar, et al., ACS Catal. 8(2018) 6216-6223.
doi: 10.1021/acscatal.8b00641
T.A. Boebel, J.F. Hartwig, J. Am. Chem. Soc. 130(2008) 7534-7535.
doi: 10.1021/ja8015878
Y.L. Liu, G. Kehr, C.G. Daniliuc, G. Erker, Chem. Eur. J. 23(2017) 12141-12144.
doi: 10.1002/chem.201701771
V. Bagutski, A. Del Grosso, J.A. Carrillo, et al., J. Am. Chem. Soc. 135(2013) 474-487.
doi: 10.1021/ja3100963
J. Lv, B. Zhao, Y. Yuan, Y. Han, Z. Shi, Nat. Commun. 11(2020) 1316.
doi: 10.1038/s41467-020-15207-x
G. Wu, X. Fu, Y. Wang, et al., Org. Lett. 22(2020) 7003-7007.
doi: 10.1021/acs.orglett.0c02552
F. Focante, I. Camurati, D. Nanni, R. Leardini, L. Resconi, Organometallics 23(2004) 5135-5141.
doi: 10.1021/om0499308
Z.J. Wang, X. Chen, L. Wu, et al., Angew. Chem. Int. Ed. 60(2021) 8500-8504.
doi: 10.1002/anie.202016573
V. Iashin, D. Berta, K. Chernichenko, et al., Chem. Eur. J. 26(2020) 13873-13879.
doi: 10.1002/chem.202001436
S. Rej, N. Chatani, J. Am. Chem. Soc. 143(2021) 2920-2929.
doi: 10.1021/jacs.0c13013
F.A. Davis, M.J.S. Dewar, J. Am. Chem. Soc. 90(1968) 3511-3515.
doi: 10.1021/ja01015a039
C. Cazorla, T.S. De Vries, E. Vedejs, Org. Lett. 15(2013) 984-987.
doi: 10.1021/ol303203m
Z. Zhao, Z. Chang, B. He, et al., Chem. Eur. J. 19(2013) 11512-11517.
doi: 10.1002/chem.201301815
J. Chen, R.A. Lalancette, F. Jäkle, Organometallics 32(2013) 5843-5851.
doi: 10.1021/om400426g
D.L. Crossley, I.A. Cade, E.R. Clark, et al., Chem. Sci. 6(2015) 5144-5151.
doi: 10.1039/C5SC01800E
A.C. Shaikh, D.S. Ranade, S. Thorat, et al., Chem. Commun. 51(2015) 16115-16118.
doi: 10.1039/C5CC06351E
M. Yusuf, K. Liu, F. Guo, R.A. Lalancette, F. Jäkle, Dalton Trans 45(2016) 4580-4587.
doi: 10.1039/C5DT05077D
D.L. Crossley, I. Vitorica-Yrezabal, M.J. Humphries, M.L. Turner, M.J. Ingleson, Chem. Eur. J. 22(2016) 12439-12448.
doi: 10.1002/chem.201602010
K. Liu, R.A. Lalancette, F. Jäkle, J. Am. Chem. Soc. 139(2017) 18170-18173.
doi: 10.1021/jacs.7b11062
S.A. Iqbal, K. Yuan, J. Cid, J. Pahl, M.J. Ingleson, Org. Biomol. Chem. 19(2021) 2949-2958.
doi: 10.1039/D1OB00018G
J. Lv, B. Zhao, Y. Han, Y. Yuan, Z. Shi, Chin. Chem. Lett. 32(2021) 691-694.
doi: 10.1016/j.cclet.2020.06.028
N. Ishida, T. Moriya, T. Goya, M. Murakami, J. Org. Chem. 75(2010) 8709-8712.
doi: 10.1021/jo101920p
L. Niu, H. Yang, R. Wang, H. Fu, Org. Lett. 14(2012) 2618-2621.
doi: 10.1021/ol300950r
V. Mukundam, S. Sa, A. Kumari, R. Das, K. Venkatasubbaiah, J. Mater. Chem. C 7(2019) 12725-12737.
doi: 10.1039/C9TC04309H
C. Zhu, Z.H. Guo, A.U. Mu, et al., J. Org. Chem. 81(2016) 4347-4352.
doi: 10.1021/acs.joc.6b00238
S. Tanaka, Y. Saito, T. Yamamoto, T. Hattori, Org. Lett. 20(2018) 1828-1831.
doi: 10.1021/acs.orglett.8b00335
Y. Li, B. Pang, H. Meng, et al., Tetrahedron Lett. 60(2019) 151286.
doi: 10.1016/j.tetlet.2019.151286
Y. Li, H. Meng, T. Liu, et al., Adv. Mater. 31(2019) 1904585.
doi: 10.1002/adma.201904585
C.R. Opie, H. Noda, M. Shibasaki, N. Kumagai, Chem. Eur. J. 25(2019) 4648-4653.
doi: 10.1002/chem.201900715
S. Olsen, M.S. Baranov, N.S. Baleeva, et al., PCCP 18(2016) 26703-26711.
doi: 10.1039/C6CP02423H
M.S. Baranov, K.M. Solntsev, N.S. Baleeva, et al., Chem. Eur. J. 20(2014) 13234-13241.
doi: 10.1002/chem.201403678
K. Dhanunjayarao, S. Sa, B.P.R. Aradhyula, K. Venkatasubbaiah, Tetrahedron 74(2018) 5819-5825.
doi: 10.1016/j.tet.2018.08.019
J. Lv, X. Chen, X.S. Xue, et al., Nature 575(2019) 336-340.
doi: 10.1038/s41586-019-1640-2
S.A. Iqbal, J. Cid, R.J. Procter, et al., Angew. Chem. Int. Ed. 58(2019) 15381-15385.
doi: 10.1002/anie.201909786
S. Rej, A. Das, N. Chatani, Chem. Sci. 12(2021) 11447-11454.
doi: 10.1039/D1SC02937A
S.A. Iqbal, J. Pahl, K. Yuan, M.J. Ingleson, Chem. Soc. Rev. 49(2020) 4564-4591.
doi: 10.1039/C9CS00763F
F.G. Oliveira, F.L. Rodrigues, A.V.B. de Oliveira, D.V.L.M. Marçal, P.M. Esteves, Struct. Chem. 28(2017) 545-553.
doi: 10.1007/s11224-017-0915-1
M. Alessi, A.L. Larkin, K.A. Ogilvie, et al., J. Org. Chem. 72(2007) 1588-1594.
doi: 10.1021/jo0620359
W. Miura, K. Hirano, M. Miura, Org. Lett. 18(2016) 3742-3745.
doi: 10.1021/acs.orglett.6b01762
X. Zou, H. Zhao, Y. Li, et al., J. Am. Chem. Soc. 141(2019) 5334-5342.
doi: 10.1021/jacs.8b13756
F. Michailidou, N. Klöcker, N.V. Cornelissen, et al., Angew. Chem. Int. Ed. 60(2021) 480-485.
doi: 10.1002/anie.202012623
J.Y. Zhou, J.B. Wang, Sci. China Chem. 46(2016) 573-578.
doi: 10.1360/N032015-00254
Chunhua Ma , Mengjiao Liu , Siyu Ouyang , Zhenwei Cui , Jingjing Bi , Yuqin Jiang , Zhiguo Zhang . Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water. Chinese Chemical Letters, 2025, 36(1): 109755-. doi: 10.1016/j.cclet.2024.109755
Tong Li , Leping Pan , Yan Zhang , Jihu Su , Kai Li , Kuiliang Li , Hu Chen , Qi Sun , Zhiyong Wang . Electrochemical construction of 2,5-diaryloxazoles via N–H and C(sp3)-H functionalization. Chinese Chemical Letters, 2024, 35(4): 108897-. doi: 10.1016/j.cclet.2023.108897
Xiaodan Wang , Yingnan Liu , Zhibin Liu , Zhongjian Li , Tao Zhang , Yi Cheng , Lecheng Lei , Bin Yang , Yang Hou . Highly efficient electrosynthesis of H2O2 in acidic electrolyte on metal-free heteroatoms co-doped carbon nanosheets and simultaneously promoting Fenton process. Chinese Chemical Letters, 2024, 35(7): 108926-. doi: 10.1016/j.cclet.2023.108926
Tao Zhou , Jing Zhou , Yunyun Liu , Jie-Ping Wan , Fen-Er Chen . Transition metal-free tunable synthesis of 3-(trifluoromethylthio) and 3-trifluoromethylsulfinyl chromones via domino C–H functionalization and chromone annulation of enaminones. Chinese Chemical Letters, 2024, 35(11): 109683-. doi: 10.1016/j.cclet.2024.109683
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Jianhui Yin , Wenjing Huang , Changyong Guo , Chao Liu , Fei Gao , Honggang Hu . Tryptophan-specific peptide modification through metal-free photoinduced N-H alkylation employing N-aryl glycines. Chinese Chemical Letters, 2024, 35(6): 109244-. doi: 10.1016/j.cclet.2023.109244
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