REVIEWS

Transition Metal-Catalyzed Asymmetric Cyclizations Involving Allyl or Propargyl Heteroatom-Dipole Precursors

  • Jian Zhang ,
  • Ying Chen ,
  • Quannan Wang ,
  • Jiahuan Shen ,
  • Yangzi Liu ,
  • Weiping Deng
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  • a College of Chemistry and Life Science, Zhejiang Normal University, Jinhua, Zhejiang 321004
    b School of Pharmacy, East China University of Science and Technology, Shanghai 200237
†These authors contributed equally to this work.
* Corresponding authors. E-mail: ;

Received date: 2022-06-17

  Revised date: 2022-07-07

  Online published: 2022-07-14

Supported by

National Natural Science Foundation of China(21971062); National Natural Science Foundation of China(22171082)

Abstract

Chiral heterocyclic compounds are an important class of chiral substances, which are widespread in many chiral drugs, pesticides and catalysts. Therefore, the efficient asymmetric synthesis of these compounds becomes a research hotspot in organic synthesis. Transition metal-catalyzed asymmetric cyclization with heteroatom-dipole precursors is an important method to construct these frameworks. Among them, the heteroatom-dipole precursors designed based on transition metal-catalyzed allyl or propargyl substitutions have been extensively studied in the past two decades and occupied an important role in this field. The transition metal-catalyzed asymmetric cyclizations with allyl or propargyl heteroatom-dipole precursors are introduced in detail. The advantages and existing problems of the current methods are analyzed, which would provide useful reference for the researchers in asymmetric synthesis and related fields.

Cite this article

Jian Zhang , Ying Chen , Quannan Wang , Jiahuan Shen , Yangzi Liu , Weiping Deng . Transition Metal-Catalyzed Asymmetric Cyclizations Involving Allyl or Propargyl Heteroatom-Dipole Precursors[J]. Chinese Journal of Organic Chemistry, 2022 , 42(10) : 3051 -3101 . DOI: 10.6023/cjoc202206028

References

[1]
(a) Royer, J. Asymmetric Synthesis of Nitrogen Heterocycles, Wiley-VCH, Weinhei, 2009.
[1]
(b) Louis, D. Q.; John, A. T. Fundamentals of Heterocyclic Chemistry, Wiley-VCH, Weinheim, 2010.
[1]
(c) Pozharskii, A. F.; Soldatenkov, A. T.; Katritzky, A. R Heterocycles in Life and Society, Wiley-VCH, Weinheim, 2011
[1]
(d) Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257.
[2]
(a) Hassner, A. Synthesis of Heterocycles via Cycloadditions I, Springer, Berlin, 2008.
[2]
(b) Hassner, A. Synthesis of Heterocycles via Cycloadditions II, Springer, Berlin, 2008.
[2]
(c) Eicher, T.; Hauptmann, S.; Speicher, A. The Chemistry of Heterocycles: Structures, Reactions, Synthesis, and Applications, Wiley-VCH, Weinheim, 2012.
[2]
(d) Hashimoto, T.; Maruoka, K. Chem. Rev. 2015, 115, 5366.
[2]
(e) Wang, H.; Gu, S.; Yan, Q.; Ding, L.; Chen, F.-E. Green Synth. Catal. 2020, 1, 12.
[2]
(f) Rago, A. J.; Dong, G. Green Synth. Catal. 2021, 2, 216.
[3]
(a) Chen, J.-R.; Hu, X.-Q.; Xiao, W.-J. Angew. Chem., Int. Ed. 2014, 53, 4038.
[3]
(b) Li, T.-R.; Wang, Y.-N.; Xiao, W.-J.; Lu, L.-Q. Tetrahedron Lett. 2018, 59, 1521.
[3]
(c) You, Y.; Li, Q.; Zhang, Y.-P.; Zhao, J.-Q.; Wang, Z.-H.; Yuan, W.-C. ChemCatChem 2022, 14, e202101887.
[3]
(d) Zhang, M.-M.; Qu, B.-L.; Shi, B.; Xiao, W.-J.; Lu, L.-Q. Chem. Soc. Rev. 2022, 51, 4146.
[4]
(a) Tsuji, J.; Takahashi, H.; Morikawa, M. Tetrahedron Lett. 1965, 6, 4387.
[4]
(b) Trost, B. M.; Strege, P. E. J. Am. Chem. Soc. 1977, 99, 1649.
[5]
(a) Imada, Y.; Yuasa, M.; Nakamura, I.; Murahashi, S.-I. J. Org. Chem. 1994, 59, 2282.
[5]
(b) Detz, R. J.; Delville, M. M. E.; Hiemstra, H.; Van Maarseveen, J. H. Angew. Chem., Int. Ed. 2008, 47, 3777.
[6]
(a) Huisgen, R. Angew. Chem., Int. Ed. 1963, 2, 565.
[6]
(b) Padwa, A. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, Wiley, New York, 2003.
[6]
(c) Tong, M.-C.; Chen, X.; Tao, H.-Y.; Wang, C.-J. Angew. Chem., Int. Ed. 2013, 52, 1237.
[7]
(a) Trost, B. M.; Vranken, D. L. V. Chem. Rev. 1996, 96, 395.
[7]
(b) Sundararaju, B.; Achard, M.; Bruneau, C. Chem. Soc. Rev. 2012, 41, 4467.
[7]
(c) Butta, N. A.; Zhang, W. Chem. Soc. Rev. 2015, 44, 7929.
[7]
(d) Cheng, Q.; Tu, H.-F.; Zheng, C.; Qu, J.-P.; Helmchen, G.; You, S.-L. Chem. Rev. 2019, 119, 1855.
[7]
(e) Ro?ssler, S. L.; Petrone, D. A.; Carreira, E. M. Acc. Chem. Res. 2019, 52, 2657.
[7]
(f) Pàmies, O.; Margalef, J.; Can?ellas, S.; James, J.; Judge, E.; Guiry, P. J.; Moberg, C.; Bäckvall, J.-E.; Pfalz, A.; Pericàs, M. A.; Diéguez, M. Chem. Rev. 2021, 121, 4373.
[8]
Trost, B. M.; Chan, D. M. T. J. Am. Chem. Soc. 1979, 101, 6429.
[9]
(a) Trost, B. M. Angew. Chem., nt. Ed. 1986, 25, 1.
[9]
(b) Liu, Y.-Z.; Wang, Z.; Huang, Z.; Zheng, X.; Yang, W.-L.; Deng, W.-P. Angew. Chem., Int. Ed. 2020, 59, 1238.
[9]
(c) Zheng, X.; Sun, H.; Yang, W.-L.; Deng, W.-P. Sci. Chin. Chem. 2020, 63, 911.
[9]
(d) Yang, W.-L.; Huang, Z.; Liu, Y.-Z.; Yu, X.; Deng, W.-P. Chin. J. Chem. 2020, 38, 1571.
[9]
(e) Trost, B. M.; Mata, G. Acc. Chem. Res. 2020, 53, 1293.
[9]
(f) Liu, Y.-Z.; Wang, Z.; Huang, Z.; Yang, W.-L.; Deng, W.-P. Org. Lett. 2021, 23, 948.
[9]
(g) Ke, M.; Liu, Z.; Zhang, K.; Zuo, S.; Chen, F. Green Synth. Catal. 2021, 2, 228.
[10]
(a) Fugami, K.; Morizawa, Y.; Ishima, K.; Nozaki, H. Tetrahedron Lett. 1985, 26, 857.
[10]
(b) Fugami, K.; Miura, K.; Morizawa, Y.; Oshima, K.; Utimoto, K.; Nozaki, H. Tetrahedron Lett. 1989, 45, 3089.
[11]
(a) Butler, D. C. D.; Inman, G. A.; Alper, H. J. Org. Chem. 2000, 65, 5887.
[11]
(b) Lin, T.-Y.; Wu, H.-H.; Feng, J.-J.; Zhang, J. Org. Lett. 2018, 20, 3587.
[11]
(c) Zhu, C.-Z.; Feng, J.-J.; Zhang, J. Chem. Commun. 2018, 54, 2401.
[12]
Trost, B. M.; Fandrick, D. R. J. Am. Chem. Soc. 2003, 125, 11836.
[13]
Dong, C.; Alper, H. Tetrahedron: Asymmetry 2004, 15, 1537.
[14]
Trost, B. M.; Osipov, M.; Dong, G. J. Am. Chem. Soc. 2010, 132, 15800.
[15]
Xu, C.-F.; Zheng, B.-H.; Suo, J.-J.; Ding, C.-H.; Hou, X.-L. Angew. Chem., Int. Ed. 2015, 54, 1604.
[16]
Li, T.-R.; Cheng, B.-Y.; Fan, S.-Q.; Wang, Y.-N.; Lu, L.-Q.; Xiao, W.-J. Chem.-Eur. J. 2016, 22, 6243.
[17]
Næsborg, L.; Tur, F.; Meazza, M.; Blom, J.; Halskov, K. S.; Jørgensen, K. A. Chem.-Eur. J. 2017, 23, 268.
[18]
Rivinoja, D. J.; Gee, Y. S.; Gardiner, M. G.; Ryan, J. H.; Hyland, C. J. T. ACS Catal. 2017, 7, 1053.
[19]
Zhang, J.-Q.; Tong, F.; Sun, B.-B.; Fan, W.-T.; Chen, J.-B.; Hu, D.; Wang, X.-W. Org. Chem. 2018, 83, 2882.
[20]
Suo, J.-J.; Liu, W.; Du, J.; Ding, C.-H.; Hou, X.-L. Chem.-Asian J. 2018, 13, 959.
[21]
Spielmann, K.; van der Lee, A.; de Figueiredo R. M.; Campagne, J.-M. Org. Lett. 2018, 20, 1444.
[22]
Spielmann, K.; Tosi, E.; Lebrun, A.; Niel, G.; van der Lee, A.; de Figueiredo, R. M.; Campagne, J.-M. Tetrahedron 2018, 74, 6497.
[23]
Jiang, F.; Yuan, F.-R.; Jin, L.-W.; Mei, G.-J.; Shi, F. ACS Catal. 2018, 8, 10234.
[24]
Vetica, F.; Bailey, S. J.; Kumar, M.; Mahajan, S.; von Essen, C.; Rissanen, K.; Enders, D. Synthesis 2020, 52, 2038.
[25]
Gao, J.; Zhang, J.; Fang, S.; Feng, J.; Lu, T.; Du, D. Org. Lett. 2020, 22, 7725.
[26]
(a) Li, Y.-Y.; Li, S.; Fan, T.; Zhang, Z.-J.; Song, J.; Gong, L.-Z. ACS Catal. 2021, 11, 14388.
[26]
(b) Zhang, Z.-J.; Wen, Y.-H.; Song, J.; Gong, L.-Z. Angew. Chem., Int. Ed. 2021, 60, 3268.
[27]
Wang, C.; Tunge, J. A. J. Am. Chem. Soc. 2008, 130, 8118.
[28]
Li, T.-R.; Tan, F.; Lu, L.-Q.; Wei, Y.; Wang, Y.-N.; Liu, Y.-Y.; Yang, Q.-Q.; Chen, J.-R.; Shi, D.-Q.; Xiao, W.-J. Nat. Commun. 2014, 5, 5500.
[29]
Leth, L. A.; Glaus, F.; Meazza, M.; Fu, L.; Thøgersen, M. K.; Bitsch, E. A.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2016, 55, 15272.
[30]
Guo, C.; Fleige, M.; Janssen-Müller, D.; Daniliuc, C. G.; Glorius, F. J. Am. Chem. Soc. 2016, 138, 7840.
[31]
Guo, C.; Janssen-Müller, D.; Fleige, M.; Lerchen, A.; Daniliuc, C. G.; Glorius, F. J. Am. Chem. Soc. 2017, 139, 4443.
[32]
Wei, Y.; Lu, L.-Q.; Li, T.-R.; Feng, B.; Wang, Q.; Xiao, W.-J.; Alper, H. Angew. Chem., Int. Ed. 2016, 55, 2200.
[33]
Li, M.-M.; Wei, Y.; Liu, J.; Chen, H.-W.; Lu, L.-Q.; Xiao, W.-J. J. Am. Chem. Soc. 2017, 139, 14707.
[34]
Mei, G.-J.; Bian, C.-Y.; Li, G.-H.; Xu, S.-L.; Zheng, W.-Q.; Shi, F. Org. Lett. 2017, 19, 3219.
[35]
Mei, G.-J.; Li, D.; Zhou, G.-X.; Shi, Q.; Cao, Z.; Shi, F. Chem. Commun. 2017, 53, 10030.
[36]
Lu, Y.-L.; Lan, J.-P.; Mao, Y.-J.; Wang, Y.-X.; Mei, G.-J.; Shi, F. Chem. Commun. 2018, 54, 13527.
[37]
Jin, J.-H.; Wang, H.; Yang, Z.-T.; Yang, W.-L.; Tang, W.; Deng, W.-P. Org. Lett. 2018, 20, 104.
[38]
Wang, C.; Li, Y.; Wu, Y.; Wang, Q.; Shi, W.; Yuan, C.; Zhou, L.; Xiao, Y.; Guo, H. Org. Lett. 2018, 20, 2880.
[39]
Mun, D.; Kim, E.; Kim, S.-G. Synthesis 2019, 51, 2359.
[40]
Zhao, H.-W.; Feng, N.-N.; Guo, J.-M.; Du, J.; Ding, W.-Q.; Wang, L.-R.; Song, X.-Q. J. Org. Chem. 2018, 83, 9291.
[41]
Suo, J.-J.; Du, J.; Jiang, Y.-J.; Chen, D.; Ding, C.-H.; Hou, X.-L. Chin. Chem. Lett. 2019, 30, 1512.
[42]
Wang, Y.-N.; Xiong, Q.; Lu, L.-Q.; Zhang, Q.-L.; Wang, Y.; Lan, Y.; Xiao, W.-J. Angew. Chem., Int. Ed. 2019, 58, 11013.
[43]
Sun, M.; Wan, X.; Zhou, S.-J.; Mei, G.-J.; Shi, F. Chem. Commun. 2019, 55, 1283.
[44]
Ismail, S. N. F. B. S.; Yang, B.; Zhao, Y. Org. Lett. 2021, 23, 2884.
[45]
Guo, J.-M.; Fan, X.-Z.; Wu, H.-H.; Tang, Z.; Bi, X.-F.; Zhang, H.; Cai, L.-Y.; Zhao, H.-W.; Zhong, Q.-D. J. Org. Chem. 2021, 86, 1712.
[46]
Gao, Y.; Zhang, X.; Zhang, X.; Miao, Z. Org. Lett. 2021, 23, 2415.
[47]
Lu, C.H.; Darvishi, S.; Khakyzadeh, V.; Li, C. Chin. Chem. Lett. 2021, 32, 405.
[48]
Wang, K.; Lin, X.; Li, Q.; Liu, Y.; Li, C. Chin. J. Catal. 2022, 43, 1812.
[49]
Wang, C.; Tunge, J. A. Org. Lett. 2006, 8, 3211.
[50]
Chen, Z.-C.; Chen, Z.; Yang, Z.-H.; Guo, L.; Du, W.; Chen, Y.-C. Angew. Chem., Int. Ed. 2019, 58, 15021.
[51]
Zhang, Q.-L.; Xiong, Q.; Li, M.-M.; Xiong, W.; Shi, B.; Lan, Y.; Lu, L.-Q.; Xiao, W.-J. Angew. Chem., Int. Ed. 2020, 59, 14096.
[52]
Knight, J, G.; Tchabanenko, K.; Stokera, P. A.; Harwood, S. J. Tetrahedron Lett. 2005, 46, 6261.
[53]
(a) Ohmatsu, K.; Imagawa, N.; Ooi, T. Nat. Chem. 2014, 6, 47.
[53]
(b) Imagawa, N.; Nagato, Y.; Ohmatsu, K.; Ooi, T. Bull. Chem. Soc. Jpn. 2016, 89, 649.
[54]
Ohmatsu, K.; Kawai, S.; Imagawa, N.; Ooi, T. ACS Catal. 2014, 4, 4304.
[55]
Tian, F.; Yang, W.-L.; Ni, T.; Zhang, J.; Deng, W.-P. Sci. China: Chem. 2021, 64, 34.
[56]
Hang, Q.-Q.; Liu, S.-J.; Yu, L.; Sun, T.-T.; Zhang, Y.-C.; Mei, G.-J.; Shi, F. Chin. J. Chem. 2020, 38, 1612.
[57]
Zhao, Z.; Yang, X.-X.; Ran, G.-Y.; Ouyang, Q.; Du, W.; Chen, Y.-C. Org. Lett. 2021, 23, 4791.
[58]
Khan, A.; Zheng, R.; Kan, Y.; Ye, J.; Xing, J.; Zhang, Y. J. Angew. Chem., Int. Ed. 2014, 53, 6439.
[59]
Khan, A.; Yang, L.; Xu, J.; Jin, L. Y.; Zhang, Y. J. Angew. Chem., Int. Ed. 2014, 53, 11257.
[60]
Khan, A.; Xing, J.; Zhao, J.; Kan, Y.; Zhang, W.; Zhang, Y. J. Chem.-Eur. J. 2015, 21, 120.
[61]
Yang, L.; Khan, A.; Zheng, R.; Jin, L. Y.; Zhang, Y. J. Org. Lett. 2015, 17, 6230.
[62]
Khan, I.; Zhao, C.; Zhang, Y. J. Chem. Commun. 2018, 54, 4708.
[63]
Liu, K.; Khan, I.; Cheng, J.; Hsueh, Y. J.; Zhang, Y. J. ACS Catal. 2018, 8, 11600.
[64]
Zhao, C.; Khan, I.; Zhang, Y. J. Chem. Commun. 2020, 56, 12431.
[65]
Gao, X.; Xia, M.; Yuan, C.; Zhou, L.; Sun, W.; Li, C.; Wu, B.; Zhu, D.; Zhang, C.; Zheng, B.; Wang, D.; Guo, H. ACS Catal. 2019, 9, 1645.
[66]
Park, J.-U.; Ahn, H.-I.; Cho, H.-J.; Xuan, Z.; Kim, J. H. Adv. Synth. Catal. 2020, 362, 1836.
[67]
Wang, J.; Zhao, L.; Rong, Q.; Lv, C.; Lu, Y.; Pan, X.; Zhao, L.; Hu, L. Org. Lett. 2020, 22, 5833.
[68]
Singha, S.; Serrano, E.; Mondal, S.; Daniliuc, C. G.; Glorius, F. Nat. Catal. 2020, 3, 48.
[69]
Liu, J.; Yu, L. Zheng, C.; Zhao, G. Angew. Chem., Int. Ed. 2021, 60, 23641.
[70]
Lv, H.-P.; Yang, X.-P.; Wang, B.-L.; Yang, H.-D.; Wang, X.-W.; Wang, Z. Org. Lett. 2021, 23, 4715.
[71]
Ming, S.; Qurban, S. A.; Du, Y.; Su, W. Chem.-Eur. J. 2021, 27, 12742.
[72]
Xiao, L.; Wei, L.; Wang, C.-J. Angew. Chem., Int. Ed. 2021, 60, 24930.
[73]
Xiong, Q.; Xiao, L.; Dong, X.-Q.; Wang, C.-J. Org. Lett. 2022, 24, 2579.
[74]
Shi, B.; Liu, J.-B.; Wang, Z.-T.; Wang, L.; Lan, Y.; Lu, L.-Q.; Xiao, W.-J. Angew. Chem. Int. Ed. 2022, 61, e202117215.
[75]
Pan, X.; Yu, L.; Wang, S.; Wu, R.; Ou, C.; Xu, M.; Chen, B.; Gao, Y.; Ni, H.-L.; Hu, P.; Wang, B.-Q.; Cao, P. Org. Lett. 2022, 24, 2099.
[76]
Rong, Z.-Q.; Yang, L.-C.; Liu, S.; Yu, Z.; Wang, Y.-N.; Tan, Z. Y.; Huang, R.-Z.; Lan, Y.; Zhao, Y. J. Am. Chem. Soc. 2017, 139, 15304.
[77]
Singha, S.; Patra, T.; Daniliuc, C. G.; Glorius, F. J. Am. Chem. Soc. 2018, 140, 3551.
[78]
Wei, Y.; Liu, S.; Li, M.-M.; Li, Y.; Lan, Y.; Lu, L.-Q.; Xiao, W.-J. J. Am. Chem. Soc. 2019, 141, 133.
[79]
Niu, B.; Wu, X.-Y.; Wei, Y.; Shi, M. Org. Lett. 2019, 21, 4859.
[80]
Ahn, H.-I.; Park, J.-U.; Xuan, Z.; Kim, J. H. Org. Biomol. Chem. 2020, 18, 9826.
[81]
Xia, C.; Wang, D.-C.; Qu, G.-R.; Guo, H.-M. Org. Chem. Front. 2020, 7, 1474.
[82]
An, X.-T.; Du, J.-Y.; Jia, Z.-L.; Zhang, Q.; Yu, K.-Y.; Zhang, Y.-Z.; Zhao, X.-H.; Fang, R.; Fan, C.-A. Chem.-Eur. J. 2020, 26, 3803.
[83]
Uno, H.; Punna, N.; Tokunaga, E.; Shiro, M.; Shibata, N. Angew. Chem., Int. Ed. 2020, 59, 8187.
[84]
Yang, G.; Ke, Y.-M.; Zhao, Y. Angew. Chem., Int. Ed. 2021, 60, 12775.
[85]
Trost, B. M.; Angle, S. R. J. Am. Chem. Soc. 1985, 107, 6123.
[86]
Fujinami, T.; Suzuki, T.; Kamiya, M.; Fukuzawa, S.; Sakai, S. Chem. Lett. 1985, 14, 199.
[87]
Trost, B. M.; McEachern, E. J. J. Am. Chem. Soc. 1999, 121, 8649.
[88]
Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1987, 109, 3792.
[89]
Larksarp, C.; Alper, H. J. Am. Chem. Soc. 1997, 119, 3709.
[90]
Raghunath, M.; Zhang, X. Tetrahedron Lett. 2005, 46, 8213.
[91]
Shaghafi, M, B.; Grote, R. E.; Jarvo, E. R. Org. Lett. 2011, 13, 5188.
[92]
Liu, Z.; Feng, X.; Du, H. Org. Lett. 2012, 14, 3154.
[93]
Wu, W.-Q.; Ding, C.-H.; Hou, X.-L. Synlett 2012, 1035.
[94]
Ma, C.; Huang, Y.; Zhao, Y. ACS Catal. 2016, 6, 6408.
[95]
Suo, J.-J.; Du, J.; Liu, Q.-R.; Chen, D.; Ding, C.-H.; Peng, Q.; Hou, X.-L. Org. Lett. 2017, 19, 6658.
[96]
(a) Cheng, Q.; Zhang, H.-J.; Yue, W.-J.; You, S.-L. Chem 2017, 3, 428.
[96]
(b) Cheng, Q.; Zhang, F.; Cai, Y.; Guo, Y.-L.; You, S.-L. Angew. Chem., Int. Ed. 2018, 57, 2134.
[97]
Du, J.; Jiang, Y.-J.; Suo, J.-J.; Wu, W.-Q.; Liu, X.-Y.; Chen, D.; Ding, C.-H.; Wei, Y.; Hou, X.-L. Chem. Commun. 2018, 54, 13143.
[98]
Wang, W.-Y.; Wu, J.-Y.; Liu, Q.-R.; Liu, X.-Y.; Ding, C.-H.; Hou, X.-L. Org. Lett. 2018, 20, 4773.
[99]
Huang, K.-X.; Xie, M.-S.; Wang, D.-C.; Sang, J.-W.; Qu, G.-R.; Guo, H.-M. Chem. Commun. 2019, 55, 13550.
[100]
Song, X.; Gu, M.; Chen, X.; Xu, L.; Ni, Q. Asian J. Org. Chem. 2019, 8, 2180.
[101]
Trost, B. M.; Zuo, Z. Angew. Chem., Int. Ed. 2021, 60, 5806.
[102]
Peng, Y.; Huo, X.; Luo, Y.; Wu, L.; Wan, B. Angew. Chem., Int. Ed. 2021, 60, 24941.
[103]
Wang, J.; Li, Y.-F.; Du, J.; Huang, S.; Ding, C.-H.; Wong, H. N. C.; Hou, X.-L. Org. Lett. 2022, 24, 1561.
[104]
Fan, T.; Song, J.; Gong, L.-Z. Angew. Chem., Int. Ed. 2022, 61, e202201678.
[105]
Mao, B.; Liu, H.; Yan, Z.; Xu, Y.; Xu, J.; Wang, W.; Wu, Y.; Guo, H. Angew. Chem., Int. Ed. 2020, 59, 11316.
[106]
Li, M.-M.; Qu, B.-L.; Xiao, W.-J.; Lu, L.-Q. Sci. Bull. 2021, 66, 1719.
[107]
Chen, C.; Chen, Z.-C.; Du, W.; Chen, Y.-C. Org. Lett. 2021, 23, 8559
[108]
Uno, H.; Kawai, K.; Araki, T.; Shiro, M.; Shibata, N. Angew. Chem., Int. Ed. 2022, 61, e202117635.
[109]
Xu, H.; Khan, S.; Li, H.; Wu, X.; Zhang, Y. J. Org. Lett. 2019, 21, 214.
[110]
Du, J.; Hua, Y.-D.; Jiang, Y.-J.; Huang, S.; Chen, D.; Ding, C.-H.; Hou, X.-L. Org. Lett. 2020, 22, 5375.
[111]
Larksarp, C.; Alper, H. J. Org. Chem. 1999, 64, 4152.
[112]
Wang, Y.-N.; Yang, L.-C.; Rong, Z.-Q.; Liu, T.-L.; Liu, R.; Zhao, Y. Angew. Chem. Int. Ed. 2018, 57, 1596.
[113]
Xu, H.; Khan, S.; Li, H.; Wu, X.; Zhang, Y. J. Org. Lett. 2019, 21, 214.
[114]
Liang, X.; Zhang, T.-Y.; Zeng, X.-Y.; Zheng, Y.; Wei, K.; Yang, Y.-R. J. Am. Chem. Soc. 2017, 139, 3364.
[115]
Zhang, M.-M.; Wang, Y.-N.; Wang, B.-C.; Chen, X.-W.; Lu, L.-Q.; Xiao, W.-J. Nat. Commun. 2019, 10, 2716.
[116]
Yang, W.-L.; Wang, Y.-L.; Li, W.; Gu, B.-M.; Wang, S.-W.; Luo, X.; Tian, B.-X.; Deng, W.-P. ACS Catal. 2021, 11, 12557.
[117]
Yang, W.-L.; Shang, X.-Y.; Luo, X.; Deng, W.-P. Angew. Chem., Int. Ed. 2022, 61, e202203661.
[118]
Khan, I.; Shah, B. H.; Zhao, C.; Xu, F.; Zhang, Y. J. Org. Lett. 2019, 21, 9452.
[119]
Zhang, J.; Gao, Y.-S.; Gu, B.-M.; Yang, W.-L.; Tian, B.-X.; Deng, W.-P. ACS Catal. 2021, 11, 3810.
[120]
Li, Q.; Pan, R.; Wang, M.; Yao, H.; Lin, A. Org. Lett. 2021, 23, 2292.
[121]
Larksarp, C.; Sellier, O.; Alper, H. J. Org. Chem. 2001, 66, 3502.
[122]
Lockwood, R. F.; Nicholas, K. M. Tetrahedron Lett. 1977, 18, 4163.
[123]
(a) Detz, R. J.; Hiemstra, H.; van Maarseveen, J. H. Eur. J. Org. Chem. 2009, 2009, 6263.
[123]
(b) Zhang, D.-Y.; Hu, X.-P. Tetrahedron Lett. 2015, 56, 283.
[123]
(c) Ljungdahl, N.; Kann, N. Angew. Chem., Int. Ed. 2009, 48, 642.
[123]
(d) Ding, C.-H.; Hou, X.-L. Chem. Rev. 2011, 111, 1914.
[123]
(e) Sakata, K.; Nishibayashi, Y. Catal. Sci. Technol. 2018, 8, 12.
[123]
(f) Roy, R.; Saha, S. RSC Adv. 2018, 8, 31129.
[123]
(g) Roh, S. W.; Choi, K.; Lee, C. Chem. Rev. 2019, 119, 4293.
[124]
Wang, Q.; Li, T.-R.; Lu, L.-Q.; Li, M.-M.; Zhang, K.; Xiao, W.-J. J. Am. Chem. Soc. 2016, 138, 8360.
[125]
Shao, W.; You, S-L. Chem.-Eur. J. 2017, 23, 12489.
[126]
Song, J.; Zhang, Z.-J.; Gong, L.-Z. Angew. Chem., Int. Ed. 2017, 56, 5212.
[127]
Lu, X.; Ge, L.; Cheng, C.; Chen, J.; Cao, W.; Wu, X. Chem.-Eur. J. 2017, 23, 7689.
[128]
Chen, H.; Lu, X.; Xia, X.; Zhu, Q.; Song, Y.; Chen, J.; Cao, W.; Wu, X. Org. Lett. 2018, 20, 1760.
[129]
Ji, D.; Wang, C.; Sun, J. Org. Lett. 2018, 20, 3710.
[130]
Wang, Y.; Zhu, L.; Wang, M.; Xiong, J.; Chen, N.; Feng, X.; Xu, Z.; Jiang, X. Org. Lett. 2018, 20, 6506.
[131]
Simlandy, A. K.; Ghosh, B.; Mukherjee, S. Org. Lett. 2019, 21, 3361.
[132]
Sun, B.-B.; Hu, Q.-X.; Hu, J.-M.; Yu, J.-Q.; Jun, J.; Wang, X.-W. Tetrahedron Lett. 2019, 60, 1967.
[133]
Zhang, Z.-J.; Zhang, L.; Geng, R.-L.; Song, J.; Chen, X.-H.; Gong, L.-Z. Angew. Chem., Int. Ed. 2019, 58, 12190.
[134]
Jiang, F.; Feng, X.; Wang, R.; Gao, X.; Jia, H.; Xiao, Y.; Zhang, C.; Guo, H. Org. Lett. 2018, 20, 5278.
[135]
Lu, S.; Ong, J.-Y.; Poh, Si. B.; Tsang, T.; Zhao, Y. Angew. Chem., Int. Ed. 2018, 57, 5714.
[136]
Zhang, Y.-C.; Zhang, B.-W.; Geng, R.-L.; Song, J. Org. Lett. 2018, 20, 7907.
[137]
Xu, Y.-W.; Hu, X.-P. Org. Lett. 2019, 21, 8091.
[138]
Zhang, J.; Ni, T.; Yang, W.-L.; Deng, W.-P. Org. Lett. 2020, 22, 4547.
[139]
Shen, J.-H.; Tian, F.; Yang, W.-L.; Deng, W.-P. Chin. J. Chem. 2021, 39, 3292.
[140]
Lu, W.-Y.; Wang, Y.; You, Y.; Wang, Z.-H.; Zhao, J.-Q.; Zhou, M.-Q.; Yuan, W.-C. J. Org. Chem. 2021, 86, 1779.
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