Selective annulation of benzamides with internal alkynes catalyzed by an electron-deficient rhodium catalyst
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* Corresponding author.
E-mail address: luyi@nju.edu.cn (Yi Lu).
Citation:
Ping Zhang, Wenju Chang, Hongyun Jiao, Yanshang Kang, Wenxuan Zhao, Peipei Cui, Yong Liang, Wei-Yin Sun, Yi Lu. Selective annulation of benzamides with internal alkynes catalyzed by an electron-deficient rhodium catalyst[J]. Chinese Chemical Letters,
;2021, 32(5): 1717-1720.
doi:
10.1016/j.cclet.2021.01.024
J. Wencel-Delord, T. Droge, F. Liu, F. Glorius, Chem. Soc. Rev. 40(2011) 4740-4761.
doi: 10.1039/c1cs15083a
K. Shin, H. Kim, S. Chang, Acc. Chem. Res. 48(2015) 1040-1052.
doi: 10.1021/acs.accounts.5b00020
Z. Chen, B. Wang, J. Zhang, et al., Org. Chem. Front. 2(2015) 1107-1295.
doi: 10.1039/C5QO00004A
G. Song, X. Wei, Acc. Chem. Res. 48(2015) 1007-1020.
doi: 10.1021/acs.accounts.5b00077
N. Umeda, H. Tsurugi, T. Satoh, M. Miura, Angew. Chem. Int. Ed. 47(2008) 4019-4022.
doi: 10.1002/anie.200800924
S. Mochida, N. Umeda, K. Hirano, T. Satoh, M. Miura, Chem. Lett. 39(2010) 744-746.
doi: 10.1246/cl.2010.744
N. Guimond, C. Gouliaras, K. Fagnou, J. Am. Chem. Soc. 132(2010) 6908-6909.
doi: 10.1021/ja102571b
T.K. Hyster, T. Rovis, J. Am. Chem. Soc. 132(2010) 10565-10569.
doi: 10.1021/ja103776u
G. Song, D. Chen, C.L. Pan, R.H. Crabtree, X.W. Li, J. Org. Chem. 75(2010) 7487-7490.
doi: 10.1021/jo101596d
H. Wang, C. Grohmann, C. Nimphius, F. Glorius, J. Am. Chem. Soc. 134(2012) 19592-19595.
doi: 10.1021/ja310153v
Y. Fukui, P. Liu, Q. Liu, et al., J. Am. Chem. Soc. 136(2014) 15607-15614.
doi: 10.1021/ja5072702
Y. Liu, Y. Yang, Y. Shi, et al., Organometallics 35(2016) 1350-1353.
doi: 10.1021/acs.organomet.6b00107
J. Mo, L. Wang, X. Cui, Org. Lett. 17(2015) 4960-4963.
doi: 10.1021/acs.orglett.5b02291
Y. Zhao, S. Li, X. Zheng, et al., Angew. Chem. Int. Ed. 56(2017) 4286-4289.
doi: 10.1002/anie.201612147
G. Zheng, X. Duan, L. Chen, et al., J. Org. Chem. 85(2020) 4543-4552.
doi: 10.1021/acs.joc.0c00018
S.Y. Hong, J. Jeong, S. Chang, Angew. Chem. Int. Ed. 56(2017) 2408-2412.
doi: 10.1002/anie.201612559
T. Piou, F. Romanov-Michailidis, M. Romanova-Michaelides, et al., J. Am. Chem. Soc. 139(2017) 1296-1310.
doi: 10.1021/jacs.6b11670
T. Uto, M. Shimizu, K. Ueura, et al., J. Org. Chem. 73(2008) 298-300.
doi: 10.1021/jo7022087
N. Umeda, H. Tsurugi, T. Satoh, M. Miura, Angew. Chem. Int. Ed. 47(2008) 4019-4022.
doi: 10.1002/anie.200800924
M. Shimizu, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 74(2009) 3478-3483.
doi: 10.1021/jo900396z
F. Romanov-Michailidis, K.F. Sedillo, J.M. Neely, T. Rovis, J. Am. Chem. Soc. 136(2015) 8892-8895.
Y. Hoshino, Y. Shibata, K. Tanaka, Adv. Synth. Catal. 356(2014) 1577-1585.
doi: 10.1002/adsc.201300884
M. Fukui, Y. Hoshino, T. Satoh, M. Miura, K. Tanaka, Adv. Synth. Catal. 356(2014) 1638-1644.
doi: 10.1002/adsc.201400084
M. Font, B. Cendón, A. Seoane, J.L. MascareÇas, M. Gulías, Angew. Chem. Int. Ed. 57(2018) 8255-8259.
doi: 10.1002/anie.201802830
B. Ye, N. Cramer, Science 338(2012) 504-506.
doi: 10.1126/science.1226938
S.G. Wang, N. Cramer, Angew. Chem. Int. Ed. 58(2019) 2514-2518.
doi: 10.1002/anie.201813953
S.G. Wang, Y. Liu, N. Cramer, Angew. Chem. Int. Ed. 58(2019) 18136-18140.
doi: 10.1002/anie.201909971
S.G. Wang, N. Cramer, ACS Catal. 10(2020) 8231-8236.
doi: 10.1021/acscatal.0c02430
C. Duchemin, N. Cramer, Angew. Chem. Int. Ed. 59(2020) 14129-14133.
doi: 10.1002/anie.202006149
Y. Sun, N. Cramer, Angew. Chem. Int. Ed. 57(2018) 15539-15543.
doi: 10.1002/anie.201810887
B. Shen, B. Wan, X. Li, Angew. Chem. Int. Ed. 57(2018) 15534-15538.
doi: 10.1002/anie.201810472
M. Tian, D. Bai, G. Zheng, J. Chang, X. Li, J. Am. Chem. Soc. 141(2019) 9527-9532.
doi: 10.1021/jacs.9b04711
X. Yang, G. Zheng, X. Li, Angew. Chem. Int. Ed. 58(2019) 322-326.
doi: 10.1002/anie.201811998
F. Wang, Z. Qi, Y. Zhao, et al., Angew. Chem. Int. Ed. 59(2020) 13288-13294.
doi: 10.1002/anie.202002208
J. Zheng, W.J. Cui, C. Zheng, S.L. You, J. Am. Chem. Soc. 138(2016) 5242-5245.
doi: 10.1021/jacs.6b02302
W.J. Cui, Z.J. Wu, Q. Gu, S.L. You, J. Am. Chem. Soc. 142(2020) 7379-7385.
doi: 10.1021/jacs.0c02813
Z.J. Jia, C. Merten, R. Gontla, et al., Angew. Chem. Int. Ed. 56(2017) 2429-2434.
doi: 10.1002/anie.201611981
E.A. Trifonova, N.M. Ankudinov, A.A. Mikhaylov, et al., Angew. Chem. Int. Ed. 57(2018) 7714-7718.
doi: 10.1002/anie.201801703
T. Li, C. Zhou, X. Yan, J. Wang, Angew. Chem. Int. Ed. 57(2018) 4048-4052.
doi: 10.1002/anie.201712691
H. Li, X. Yan, J. Zhang, et al., Angew. Chem. Int. Ed. 58(2019) 6732-6736.
doi: 10.1002/anie.201901619
N. Guimond, S.I. Gorelsky, K. Fagnou, J. Am. Chem. Soc. 133(2011) 6449-6457.
doi: 10.1021/ja201143v
G. Song, X. Gong, X. Li, J. Org. Chem. 76(2011) 7583-7589.
doi: 10.1021/jo201266u
Z. Shi, C. Tang, N. Jiao, Adv. Synth. Catal. 354(2012) 2695-2700.
doi: 10.1002/adsc.201200372
X. Xu, Y. Liu, C.M. Park, Angew. Chem. Int. Ed. 51(2012) 9372-9376.
doi: 10.1002/anie.201204970
D.G. Yu, F. de Azambuja, T. Gensch, C.G. Daniliuc, F. Glorius, Angew. Chem. Int. Ed. 53(2014) 9650-9654.
doi: 10.1002/anie.201403782
N.S. Upadhyay, V.H. Thorat, R. Sato, et al., Green Chem. 19(2017) 3219-3224.
doi: 10.1039/C7GC01221G
M. Fukui, Y. Shibata, Y. Hoshino, et al., Chem. Asian J. 11(2016) 2260-2264.
doi: 10.1002/asia.201600943
E. Kudo, Y. Shibata, M. Yamazaki, et al., Chem. Eur. J. 22(2016) 14190-14194.
doi: 10.1002/chem.201603499
J. Terasawa, Y. Shibata, M. Fukui, K. Tanaka, Molecules 23(2018) 3325-3337.
doi: 10.3390/molecules23123325
G. Mihara, K. Ghosh, Y. Nishii, M. Miura, Org. Lett. 22(2020) 5706-5711.
doi: 10.1021/acs.orglett.0c02112
Y. Lu, H.W. Wang, J.E. Spangler, et al., Chem. Sci. 6(2015) 1923-1927.
doi: 10.1039/C4SC03350G
H.W. Wang, P.P. Cui, Y. Lu, W.Y. Sun, J.Q. Yu, J. Org. Chem. 81(2016) 3416-3422.
doi: 10.1021/acs.joc.6b00083
H.W. Wang, Y. Lu, B. Zhang, et al., Angew. Chem. Int. Ed. 56(2017) 7449-7453.
doi: 10.1002/anie.201703300
Y.S. Kang, P. Zhang, M.Y. Li, et al., Angew. Chem. Int. Ed. 58(2019) 9099-9103.
doi: 10.1002/anie.201903511
P. Zhang, W. Chang, Y.S. Kang, et al., Org. Lett. 22(2020) 9462-9467.
doi: 10.1021/acs.orglett.0c03425
L. Li, W.W. Brennessel, W.D. Jones, Organometallics 28(2009) 3492-3500.
doi: 10.1021/om9000742
M.D. Lotz, N.M. Camasso, A.J. Canty, M.S. Sanford, Organometallics 36(2017) 165-171.
doi: 10.1021/acs.organomet.6b00437
J.Q. Wu, S.S. Zhang, H. Gao, et al., J. Am. Chem. Soc. 139(2017) 3537-3545.
doi: 10.1021/jacs.7b00118
X.G. Liu, H. Gao, S.S. Zhang, Q. Li, H. Wang, ACS Catal. 7(2017) 5078-5086.
doi: 10.1021/acscatal.7b00677
K.L. Bay, Y.F. Yang, K.N. Houk, J. Organomet. Chem. 864(2018) 19-25.
doi: 10.1016/j.jorganchem.2017.12.026
I. Funes-Ardoiz, F. Maseras, Angew. Chem. Int. Ed. 55(2016) 2764-2767.
doi: 10.1002/anie.201510540
J. Jiang, H. Liu, L. Cao, et al., ACS Catal. 9(2019) 9387-9392.
doi: 10.1021/acscatal.9b02952
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
Yujia Shi , Yan Qiao , Pengfei Xie , Miaomiao Tian , Xingwei Li , Junbiao Chang , Bingxian Liu . Rhodium-catalyzed enantioselective in situ C(sp3)−H heteroarylation by a desymmetrization approach. Chinese Chemical Letters, 2024, 35(10): 109544-. doi: 10.1016/j.cclet.2024.109544
Jindian Duan , Xiaojuan Ding , Pui Ying Choy , Binyan Xu , Luchao Li , Hong Qin , Zheng Fang , Fuk Yee Kwong , Kai Guo . Oxidative spirolactonisation for modular access of γ-spirolactones via a radical tandem annulation pathway. Chinese Chemical Letters, 2024, 35(10): 109565-. doi: 10.1016/j.cclet.2024.109565
Jian-Rong Li , Jieying Hu , Lai-Hon Chung , Jilong Zhou , Parijat Borah , Zhiqing Lin , Yuan-Hui Zhong , Hua-Qun Zhou , Xianghua Yang , Zhengtao Xu , Jun He . Insight into stable, concentrated radicals from sulfur-functionalized alkyne-rich crystalline frameworks and application in solar-to-vapor conversion. Chinese Journal of Structural Chemistry, 2024, 43(8): 100380-100380. doi: 10.1016/j.cjsc.2024.100380
Guang Xu , Cuiju Zhu , Xiang Li , Kexin Zhu , Hao Xu . Copper-catalyzed asymmetric [4+1] annulation of yne–allylic esters with pyrazolones. Chinese Chemical Letters, 2025, 36(4): 110114-. doi: 10.1016/j.cclet.2024.110114
Hai-Yang Song , Jun Jiang , Yu-Hang Song , Min-Hang Zhou , Chao Wu , Xiang Chen , Wei-Min He . Supporting-electrolyte-free electrochemical [2 + 2 + 1] annulation of benzo[d]isothiazole 1,1-dioxides, N-arylglycines and paraformaldehyde. Chinese Chemical Letters, 2024, 35(6): 109246-. doi: 10.1016/j.cclet.2023.109246
Yunkang Tong , Haiqiao Huang , Haolan Li , Mingle Li , Wen Sun , Jianjun Du , Jiangli Fan , Lei Wang , Bin Liu , Xiaoqiang Chen , Xiaojun Peng . Cooperative bond scission by HRP/H2O2 for targeted prodrug activation. Chinese Chemical Letters, 2024, 35(12): 109663-. doi: 10.1016/j.cclet.2024.109663
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Ruru Li , Qian Liu , Hui Li , Fengbin Sun , Zhurui Shen . Rational design of dual sites induced local electron rearrangement for enhanced photocatalytic oxygen activation. Chinese Chemical Letters, 2024, 35(11): 109679-. doi: 10.1016/j.cclet.2024.109679
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