Synthesis 2022; 54(02): 315-333
DOI: 10.1055/a-1631-1606
short review

α-Csp3–H Bond Functionalization of Simple Ethers in Radical Reactions

Yanping Feng
,
Xiajuan Ye
,
Dayun Huang
,
Sheng-rong Guo
This work was funded by the Natural Science Foundation of Zhejiang Province (LY19B020001, LQ18B020001) and Foundation of University Student Innovation Program (2021R434001) for financial support.


Abstract

The direct α-Csp3–H functionalization of simple ethers is a vital strategy among radical reactions. This review discusses their applications according to the starting materials: (1) reactions with alkenes or alkynes; (2) reactions with other unsaturated compounds; and (3) reactions with nucleophilic partners. Mechanisms like radical addition, C–H activation, elimination, metal-catalyzed coupling, cyclization, oxidation, and rearrangement will be analyzed herein.

1 Introduction

2 Reactions with Alkenes or Alkynes

3 Reactions with Other Unsaturated Compounds

4 Reactions with Nucleophilic Partners

5 Oxidation of Ethers

6 Conclusions



Publication History

Received: 22 July 2021

Accepted after revision: 02 September 2021

Accepted Manuscript online:
02 September 2021

Article published online:
20 October 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References

    • 2a Zhao J, Zhou W, Han J, Li G, Pan Y. Tetrahedron Lett. 2013; 54: 6507
    • 2b Liu Z, Wang L, Liu D, Wang Z. Synlett 2015; 26: 2849
    • 2c Fang Z, Wei C, Lin J, Liu Z, Wang W, Xu C, Wang X, Wang Y, Wang Y. Org. Biomol. Chem. 2017; 15: 9974
    • 2d Ji P.-Y, Liu Y.-F, Xu J.-W, Luo W.-P, Liu Q, Guo C.-G. J. Org. Chem. 2017; 82: 2965
    • 2e Jang Y.-J, Shih Y.-K, Liu J.-Y, Kuo W.-Y, Yao C.-F. Chem. Eur. J. 2003; 9: 2123
    • 2f Sølvhøj A, Ahlburg A, Madsen R. Chem. Eur. J. 2015; 21: 16272
    • 2g Paul S, Guin J. Green Chem. 2017; 19: 2530
    • 2h Gu H, Wang C. Org. Biomol. Chem. 2015; 13: 5880
    • 2i Ge X, Hoang KL. M, Leow ML, Liu X.-W. RSC Adv. 2014; 4: 45191
    • 3a Chen R, Wang K.-K, Wang Z.-Y, Ma X, Wang D, Zhang A.-a, Liu L. ChemistrySelect 2020; 5: 2078
    • 3b Li J, Li J, Yuan S, Zhang Q, Li D. Asian J. Org. Chem. 2019; 8: 1842
    • 3c Cheng K, Huang L, Zhang Y. Org. Lett. 2009; 11: 2908
    • 3d Sun H, Zhang Y, Guo F, Zha Z, Wang Z. J. Org. Chem. 2012; 77: 3563
  • 4 Hou J, Ee A, Cao H, Ong H.-W, Xu JH, Wu J. Angew. Chem. Int. Ed. 2018; 57: 17220
    • 5a Capaldo L, Merli D, Fagnoni M, Ravelli D. ACS Catal. 2019; 9: 3054
    • 5b Fan X.-Z, Rong J.-W, Wu H.-L, Zhou Q, Deng H.-P, Tan JD, Xue C.-W, Wu L.-Z, Tao H.-R, Wu J. Angew. Chem. Int. Ed. 2018; 57: 8514
    • 5c Yamada KI, Maekawa M, Akindele T, Nakano M, Yamamoto Y, Tomioka K. J. Org. Chem. 2008; 73: 9535
    • 5d Yamada KI, Maekawa M, Yamamoto Y, Nakano M, Akindele T, Tomioka K. Tetrahedron Lett. 2009; 50: 6040
    • 5e Rohe S, Morris AO, McCallum T, Barriault L. Angew. Chem. Int. Ed. 2018; 57: 15664
    • 5f Morton CM, Zhu Q, Ripberger H, Troian-Gautier L, Toa ZS, Knowles RR, Alexanian EJ. J. Am. Chem. Soc. 2019; 141: 13253
    • 5g Ohmatsu K, Suzuki R, Furukawa Y, Sato M, Ooi T. ACS Catal. 2020; 10: 2627
    • 5h Kamijo S, Takao G, Kamijo K, Tsuno T, Ishiguro K, Murafuji T. Org. Lett. 2016; 18: 4912
    • 5i Lan Y, Fan P, Liu X.-W, Meng F.-F, Ahmad T, Xu Y.-H, Loh T.-P. Chem. Commun. 2017; 53: 12353
    • 5j Chen R, Yu J.-T, Cheng J. Org. Biomol. Chem. 2018; 16: 1823
    • 5k More SG, Suryavanshi G. Org. Biomol. Chem. 2019; 17: 3239
    • 5l Ravelli D, Montanaro S, Zema M, Fagnoni M, Albini A. Adv. Synth. Catal. 2011; 353: 3295
    • 5m Raviola C, Ravelli D. Synlett 2019; 30: 803
    • 5n Jeong IH, Jeon SL, Kim BT. Synth. Commun. 2000; 30: 4309
    • 5o Abadie B, Jardel D, Pozzi G, Toullec P, Vincent JM. Chem. Eur. J. 2019; 25: 16120
    • 5p Kuang Y, Wang K, Shi X, Huang X, Meggers E, Wu J. Angew. Chem. Int. Ed. 2019; 58: 16859
    • 5q Capaldo L, Fagnoni M, Ravelli D. Chem. Eur. J. 2017; 23: 6527
    • 6a Xia D, Li Y, Miao T, Li P, Wang L. Green Chem. 2017; 19: 1732
    • 6b Wei W.-T, Zhou M.-B, Fan J.-H, Liu W, Song R.-J, Liu Y, Hu M, Xie P, Li J.-H. Angew. Chem. Int. Ed. 2013; 52: 3638
    • 6c Li Y, Sun S, Cheng J, Yu J. Org. Biomol. Chem. 2020; 18: 650
    • 6d Zhang M, Xie P, Zhao W, Niu B, Wu W, Bian Z, Pittman CU. Jr, Zhou A. J. Org. Chem. 2015; 80: 4176
    • 6e Sun K, Li G, Li Y, Yu J, Zhao Q, Zhang Z, Zhang G. Adv. Synth. Catal. 2020; 362: 1947
    • 6f Gao L.-H, Zhang J.-Y, Song S.-Z, Cao T.-T, Ge G.-P, Li Q, Wei W.-T. Org. Biomol. Chem. 2019; 17: 7674
    • 6g Liu Y, Wang Q.-L, Zhou C.-S, Xiong B.-Q, Zhang P.-L, Yang C.-a, Tang K.-W. J. Org. Chem. 2017; 82: 7394
    • 6h Chu X.-Q, Meng H, Zi Y, Xu X.-P, Ji S.-J. Chem. Commun. 2014; 50: 9718
    • 6i Gu L, Gao Y, Ai X, Jin C, He Y, Li G, Yuan M. Chem. Commun. 2017; 53: 12946
    • 7a Zhang J, Li P, Wang L. Org. Biomol. Chem. 2014; 12: 2969
    • 7b Xie X, Liu J, Wang L, Wang M. Eur. J. Org. Chem. 2020; 2020: 1534
    • 7c Yang Y, Huang H, Zhang X, Zeng W, Liang Y. Synthesis 2013; 45: 3137
  • 8 Ye Y.-X, Ou Y.-L, Liang H, Zhou H.-Y, Ye B.-H. Catal. Commun. 2018; 106: 96
    • 9a Tusun X, Lu C.-D. Synlett 2013; 24: 1693
    • 9b Huang L, Cheng K, Yao B, Zhao J, Zhang Y. Synthesis 2009; 3504
    • 9c Zhang Y, Li C.-J. Tetrahedron Lett. 2004; 45: 7581
    • 9d Chen Z, Zhang Y.-X, An Y, Song X.-L, Wang Y.-H, Zhu L.-J, Guo L. Eur. J. Org. Chem. 2009; 2009: 5146
    • 9e Chen L, Yang J, Li L, Weng Z, Kang Q. Tetrahedron Lett. 2014; 55: 6096
    • 9f Li J, Zhang J, Tan H, Wang DZ. Org. Lett. 2015; 17: 2522
    • 9g Zhang M, Zhao Y, Chen W. Synthesis 2017; 49: 1342
    • 9h Deng H.-P, Fan X.-Z, Chen Z.-H, Xu Q.-H, Wu J. J. Am. Chem. Soc. 2017; 139: 13579
    • 10a Wan Z.-j, Yuan X.-f, Luo J. Org. Biomol. Chem. 2020; 18: 3258
    • 10b Go SY, Lee GS, Hong SH. Org. Lett. 2018; 20: 4691
    • 11a Wei W.-T, Song R.-J, Ouyang X.-H, Li Y, Li H.-B, Li J.-H. Org. Chem. Front. 2014; 1: 484
    • 11b Chen W, Zhang Y, Li P, Wang L. Org. Chem. Front. 2018; 5: 855
    • 12a Kong D.-L, Cheng L, Wu H.-R, Li Y.-X, Wang D, Liu L. Org. Biomol. Chem. 2016; 14: 2210
    • 12b Pan C, Zhang H, Zhu C. Tetrahedron Lett. 2016; 57: 595
    • 12c Wang J, Mou X.-Q, Zhang B.-H, Liu W.-T, Yang C, Xu L, Xu Z.-L, Wang S.-H. Tetrahedron Lett. 2016; 57: 1239
    • 13a Yuan H, Liu Z, Shen Y, Zhao H, Li C, Jia X, Li J. Adv. Synth. Catal. 2019; 361: 2009
    • 13b Feng S, Li T, Du C, Chen P, Song D, Li J, Xie X, She X. Chem. Commun. 2017; 53: 4585
    • 13c Anton-Torrecillas C, Felipe-Blanco D, Gonzalez-Gomez JC. Org. Biomol. Chem. 2016; 14: 10620
    • 13d Pan C, Han J, Zhu C. Sci. China Chem. 2014; 57: 1172
    • 13e Xu Y, Chen H, Li W, Xie Q, Yu L, Shao L. ChemistrySelect 2017; 2: 8033
    • 14a Kamijo S, Hoshikawa T, Inoue M. Tetrahedron Lett. 2011; 52: 2885
    • 14b Wang L, Tian Q, Bin C, Zhang G. Tetrahedron Lett. 2019; 60: 2084
  • 15 Averina EB, Vasilenko DA, Samoilichenko YV, Grishin YK, Rybakov VB, Kuznetsova TS, Zefirov NS. Synthesis 2014; 46: 1107
    • 16a Yoshimitsu T, Arano Y, Nagaoka H. J. Org. Chem. 2005; 70: 2342
    • 16b Yoshimitsu T, Arano Y, Nagaoka H. J. Org. Chem. 2003; 68: 625
    • 16c Yoshimitsu T, Tsunoda M, Nagaoka H. Chem. Commun. 1999; 1745
    • 16d Reckenthäler M, Neudörfl JM, Zorlu E, Griesbeck AG. J. Org. Chem. 2016; 81: 7211
    • 17a Zeng H, Lu D, Gong Y. Eur. J. Org. Chem. 2017; 2017: 7231
    • 17b Yang S, Zhu S, Lu D, Gong Y. Org. Lett. 2019; 21: 2019
    • 17c Supranovich VI, Levin VV, Dilman AD. Org. Lett. 2019; 21: 4271
    • 17d Vil VA, Grishin SS, Baberkina EP, Kostyagina VA, Kovalenko AE, Terent’ev AO. Tetrahedron Lett. 2020; 61: 152150
    • 17e Yamada KI, Yamamoto Y, Tomioka K. Org. Lett. 2003; 5: 1797
    • 17f Mutra MR, Dhandabani GK, Wang J.-J. Adv. Synth. Catal. 2018; 360: 3960
    • 18a Wang X, Wang Z. Tetrahedron 2014; 70: 6728
    • 18b Lipp A, Lahm G, Opatz T. J. Org. Chem. 2016; 81: 4890
    • 20a Zhao H, Jin J. Org. Lett. 2019; 21: 6179
    • 20b Okugawa N, Moriyama K, Togo H. Eur. J. Org. Chem. 2015; 2015: 4973
    • 20c Zhou J, Zou Y, Zhou P, Chen Z, Li J. Org. Chem. Front. 2019; 6: 1594
    • 20d McCallum T, Jouanno LA, Cannillo A, Barriault L. Synlett 2016; 27: 1282
    • 20e Huang C, Li J, Liu W, Li C. Chem. Sci. 2019; 10: 5018
    • 20f Wang S, Fan Y, Zhao H, Wang J, Zhang S, Wang W. Synlett 2019; 30: 2096
    • 20g Quattrini MC, Fujii S, Yamada K, Fukuyama T, Ravelli D, Fagnoni M, Ryu I. Chem. Commun. 2017; 53: 2335
    • 20h Devari S, Shah BA. Chem. Commun. 2016; 52: 1490
    • 21a Vijeta A, Reisner E. Chem. Commun. 2019; 55: 14007
    • 21b Liu S, Liu A, Zhang Y, Wang W. Chem. Sci. 2017; 8: 4404
    • 21c Liang X, Niu L, Wang S, Liu J, Lei A. Org. Lett. 2019; 21: 2441
    • 21d Huang H, Strater ZM, Lambert TH. J. Am. Chem. Soc. 2020; 142: 1698
    • 21e He T, Yu L, Zhang L, Wang L, Wang W. Org. Lett. 2011; 13: 5016
    • 21f Zhang Y, Teuscher KB, Ji H. Chem. Sci. 2016; 7: 2111
    • 22a Sun W, Xie Z, Liu J, Wang L. Org. Biomol. Chem. 2015; 13: 4596
    • 22b Lai M, Li Y, Wu Z, Zhao M, Ji X, Liu P, Zhang X. Asian J. Org. Chem. 2018; 7: 1118
    • 22c Wu Z, Pi C, Cui X, Bai J, Wu Y. Adv. Synth. Catal. 2013; 355: 1971
    • 22d Fang L, Chen L, Yu J, Wang L. Eur. J. Org. Chem. 2015; 2015: 1910
    • 23a Yang K, Li D, Zhang L, Chen Q, Tang T. RSC Adv. 2018; 8: 13671
    • 23b Jin L, Feng J, Lu G, Cai C. Adv. Synth. Catal. 2015; 357: 2105
    • 23c Yang Q, Choy PY, Wu Y, Fan B, Kwong FY. Org. Biomol. Chem. 2016; 14: 2608
    • 23d Li Y, Wang M, Fan W, Qian F, Li G, Lu H. J. Org. Chem. 2016; 81: 11743
    • 24a Xie Z, Cai Y, Hu H, Lin C, Jiang J, Chen Z, Wang L, Pan Y. Org. Lett. 2013; 15: 4600
    • 24b Yuan J, Fu J, Yin J, Dong Z, Xiao Y, Mao P, Qu L. Org. Chem. Front. 2018; 5: 2820
    • 24c Singsardar M, Laru S, Mondal S, Hajra A. J. Org. Chem. 2019; 84: 4543
    • 24d Yu Y, Jiao L, Wang J, Wang H, Yu C, Hao E, Boens N. Chem. Commun. 2017; 53: 581
    • 24e Correa A, Fiser B, Gómez-Bengoa E. Chem. Commun. 2015; 51: 13365
    • 24f Dong J, Xia Q, Lv X, Yan C, Song H, Liu Y, Wang Q. Org. Lett. 2018; 20: 5661
    • 25a Jafarpour F, Darvishmolla M. Org. Biomol. Chem. 2018; 16: 3396
    • 25b Wang C, Mi X, Li Q, Li Y, Huang M, Zhang J, Wu Y, Wu Y. Tetrahedron 2015; 71: 6689
    • 25c Doan SH, Nguyen VH. H, Nguyen TH, Pham PH, Nguyen NN, Phan AN. Q, Tu TN, Phan NT. RSC Adv. 2018; 8: 10736
    • 25d Niu B, Zhao W, Ding Y, Bian Z, Pittman CU. Jr, Zhou A, Ge H. J. Org. Chem. 2015; 80: 7251
    • 26a Ghosh T, Maity P, Ranu BC. Org. Lett. 2018; 20: 1011
    • 26b Mane KD, Mukherjee A, Vanka K, Suryavanshi G. J. Org. Chem. 2019; 84: 2039
    • 26c Li S, Wang B, Dong G, Li C, Liu H. RSC Adv. 2018; 8: 13454
    • 26d Samanta S, Hajra A. J. Org. Chem. 2019; 84: 4363
    • 26e Li Q, Hu W, Hu R, Lu H, Li G. Org. Lett. 2017; 19: 4676
  • 27 Shen L, Gao X, Luan N, Liu Z, Li J, Zou D, Wu Y, Wu Y. Org. Biomol. Chem. 2020; 18: 1738
  • 28 Li Z.-L, Sun K.-K, Wu P.-Y, Cai C. J. Org. Chem. 2019; 84: 6830
  • 29 Sun Q, Zhang Y.-Y, Sun J, Han Y, Jia X, Yan C.-G. J. Org. Chem. 2018; 83: 6640
    • 30a Ding R, Lu W.-G, Ci H, Mao Y.-Y, Liu L. ChemistrySelect 2019; 4: 6954
    • 30b Wen J, Zhang F, Shi W, Lei A. Chem. Eur. J. 2017; 23: 8814
    • 30c Wang Q, Lou J, Wu P, Wu K, Yu Z. Adv. Synth. Catal. 2017; 359: 2981
    • 30d Li Z, Yu R, Li H. Angew. Chem. Int. Ed. 2008; 47: 7497
    • 31a Buslov I, Hu X. Adv. Synth. Catal. 2014; 356: 3325
    • 31b Gu L.-H, Zhang D.-D, Qi Q.-R, Yin P, He L. Tetrahedron 2014; 70: 8155
    • 31c Campos J, Goforth SK, Crabtree RH, Gunnoe TB. RSC Adv. 2014; 4: 47951
    • 31d Yue Q, Xiao Z, Ran Z, Yuan S, Zhang Q, Li D. Org. Chem. Front. 2018; 5: 967
    • 31e He L, Yu J, Zhang J, Yu X.-Q. Org. Lett. 2007; 9: 2277
    • 31f Wang H, Li Y, Wang Z, Lou J, Xiao Y, Qiu G, Hu X, Altenbach HJ, Liu P. RSC Adv. 2014; 4: 25287
    • 31g Sun K, Wang X, Li G, Zhu Z, Jiang Y, Xiao B. Chem. Commun. 2014; 50: 12880
    • 31h Zhou L, Tang S, Qi X, Lin C, Liu K, Liu C, Lan Y, Lei A. Org. Lett. 2014; 16: 3404
    • 31i Yue Q, Xiao Z, Kuang Z, Su Z, Zhang Q, Li D. Adv. Synth. Catal. 2018; 360: 1193
  • 32 Pan Z, Fan Z, Lu B, Cheng J. Adv. Synth. Catal. 2018; 360: 1761
    • 33a Yang Q, Choy PY, Fu WC, Fan B, Kwong FY. J. Org. Chem. 2015; 80: 11193
    • 33b Wu X, Qiao K, Qin H, Zhang D, Gao D, Yang Z, Fang Z, Guo K. Org. Chem. Front. 2019; 6: 2672
    • 33c Aruri H, Singh U, Sharma S, Gudup S, Bhogal M, Kumar S, Singh D, Gupta VK, Kant R, Vishwakarma RA, Singh PP. J. Org. Chem. 2015; 80: 1929
    • 33d Luo Z, Jiang Z, Jiang W, Lin D. J. Org. Chem. 2018; 83: 3710
    • 33e Sun B, Yan Z, Jin C, Su W. Synlett 2018; 29: 2432
    • 33f Pan S, Liu J, Li H, Wang Z, Guo X, Li Z. Org. Lett. 2010; 12: 1932
    • 33g Huang R, Xie C, Huang L, Liu J. Tetrahedron 2013; 69: 577
    • 33h Guo H.-G, Xia C, Niu H.-Y, Zhang X.-T, Kong S.-N, Wang D.-C, Qu G.-R. Adv. Synth. Catal. 2011; 353: 53
    • 33i Abebe H, Vidavalur S, Battula VR. ChemistrySelect 2017; 2: 4165
    • 33j Wu J, Zhou Y, Zhou Y, Chiang C.-W, Lei A. ACS Catal. 2017; 7: 8320
    • 33k Singh MK, Akula HK, Satishkumar S, Stahl L, Lakshman MK. ACS Catal. 2016; 6: 1921
    • 33l Zhu K, Wang L, Chen Q, He M. Tetrahedron Lett. 2015; 56: 4943
    • 34a Wang M.-K, Zhou Z.-l, Tang R.-Y, Zhang X.-G, Deng C.-l. Synlett 2013; 24: 737
    • 34b Barks JM, Gilbert BC, Parsons AF, Upeandran B. Tetrahedron Lett. 2000; 41: 6249
    • 34c Ye B, Zhao J, Zhao K, McKenna JM, Toste FD. J. Am. Chem. Soc. 2018; 140: 8350
    • 34d Baati R, Valleix A, Mioskowski C, Barma DK, Falck JR. Org. Lett. 2000; 2: 485
    • 35a Kumar GS, Pieber B, Reddy KR, Kappe CO. Chem. Eur. J. 2012; 18: 6124
    • 35b Barve BD, Wu Y.-C, El-Shazly M, Korinek M, Cheng Y.-B, Wang J.-J, Chang F.-R. Tetrahedron 2015; 71: 2290
    • 35c Barve BD, Wu Y.-C, El-Shazly M, Korinek M, Cheng Y.-B, Wang J.-J, Chang F.-R. Org. Lett. 2014; 16: 1912
    • 36a Jiang H, Tang X, Liu S, Wang L, Shen H, Yang J, Wang H, Gui Q. Org. Biomol. Chem. 2019; 17: 10223
    • 36b Guo Z, Jin C, Zhou J, Su W. RSC Adv. 2016; 6: 79016
    • 36c Xu X, Sun J, Lin Y, Cheng J, Li P, Yan Y, Shuai Q, Xie Y. Org. Biomol. Chem. 2017; 15: 9875
    • 36d Ren Z, Zhao MN, Guan Z. RSC Adv. 2016; 6: 16516
    • 37a Chen L, Shi E, Liu Z, Chen S, Wei W, Li H, Xu K, Wan X. Chem. Eur. J. 2011; 17: 4085
    • 37b Wang Q, Geng H, Chai W, Zeng X, Xu M, Zhu C, Fu R, Yuan R. Eur. J. Org. Chem. 2014; 2014: 6850
    • 37c Raju KB, Kumar BN, Nagaiah K. RSC Adv. 2014; 4: 50795
    • 37d Wang Q, Feng J, Chai W, Geng H, Xu M, Wang K, Xu C, Fu R, Yuan R. Tetrahedron Lett. 2014; 55: 4785
    • 37e Wang Q, Zheng H, Chai W, Chen D, Zeng X, Fu R, Yuan R. Org. Biomol. Chem. 2014; 12: 6549
    • 37f Majji G, Rajamanickam S, Khatun N, Santra SK, Patel BK. J. Org. Chem. 2015; 80: 3440
    • 37g Majji G, Guin S, Rout SK, Behera A, Patel BK. Chem. Commun. 2014; 50: 12193
    • 38a Guo S.-r, Yuan Y.-q, Xiang J.-n. Org. Lett. 2013; 15: 4654
    • 38b Zhu X, Xie X, Li P, Guo J, Wang L. Org. Lett. 2016; 18: 1546
    • 38c Kulangiappar K, Anbukulandainathan M, Raju T. Synth. Commun. 2014; 44: 2494
    • 38d Sano R, Kudo A, Tsubogo T, Uchiro H. Asian J. Org. Chem. 2018; 7: 724
    • 38e Singh M, Yadav LD. S, Singh RK. P. Tetrahedron Lett. 2019; 60: 810
    • 38f Zhao F, Tan Q, Wang D, Chen J, Deng G. Adv. Synth. Catal. 2019; 361: 4075
    • 38g Guo S, He W, Xiang J, Yuan Y. Tetrahedron Lett. 2014; 55: 6407
    • 38h Guo S, He W, Xiang J, Yuan Y. Chem. Commun. 2014; 50: 8578
    • 38i Guo S, He W, Xiang J, Yuan Y. Tetrahedron Lett. 2015; 56: 2159
    • 38j Bao R, Feng Y, Deng D, Huang D, Sun X. Asian J. Org. Chem. 2021; 10: 1884
    • 39a Zhang J.-R, Liao Y.-Y, Deng J.-C, Feng K.-Y, Zhang M, Ning Y.-Y, Lin Z.-W, Tang R.-Y. Chem. Commun. 2017; 53: 7784
    • 39b Guo T, Wei X.-N, Liu Y, Zhang P.-K, Zhao Y.-H. Org. Chem. Front. 2019; 6: 1414
    • 39c Zhang J, Song C, Sheng L, Liu P, Sun P. J. Org. Chem. 2019; 84: 2191
    • 40a Hoshikawa T, Yoshioka S, Kamijo S, Inoue M. Synthesis 2013; 45: 874
    • 40b Hasegawa M, Ishii H, Fuchigami T. Tetrahedron Lett. 2002; 43: 1503
    • 40c Kamijo S, Tao K, Takao G, Murooka H, Murafuji T. Tetrahedron Lett. 2015; 56: 1904
    • 41a Du Y.-D, Xu Z.-J, Zhou C.-Y, Che C.-M. Org. Lett. 2019; 21: 895
    • 41b Du Y.-D, Zhou C.-Y, To W.-P, Wang H.-X, Che C.-M. Chem. Sci. 2020; 11: 4680
    • 41c Bao P, Meng N, Lv Y, Yue H, Li J, Wei W. Org. Chem. Front. 2019; 6: 3983
    • 41d Bao P, Yue H, Meng N, Zhao X, Li J, Wei W. Org. Lett. 2019; 21: 7218
    • 42a Wang J, Xu Z, Guo Z, Deng Q, Zhou C, Wan X, Che C. Chem. Commun. 2012; 48: 4299
    • 42b Thrun F, Butschke B, Graening T. Chem. Eur. J. 2012; 18: 4854
    • 42c Lovely CJ, Flores JA, Meng X, Dias HR. Synlett 2009; 129
    • 42d Fraile JM, García JI, Mayoral JA, Roldán M. Org. Lett. 2007; 9: 731
    • 42e Fraile JM, López-Ram-de-Viu P, Mayoral JA, Roldán M, Santafé-Valero J. Org. Biomol. Chem. 2011; 9: 6075
    • 42f Bonge HT, Hansen T. Synthesis 2009; 91
    • 42g Adams J, Poupart MA, Grenier L, Schaller C, Ouimet N, Frenette R. Tetrahedron Lett. 1989; 30: 1749
    • 42h Tortoreto C, Achard T, Zeghida W, Austeri M, Guénée L, Lacour J. Angew. Chem. Int. Ed. 2012; 51: 5847
    • 43a Tian H, Xia Q, Wang Q, Dong J, Wang Q. Org. Lett. 2019; 21: 4585
    • 43b Wang J, Huang B, Gao Y, Yang C, Xia W. J. Org. Chem. 2019; 84: 6895
    • 43c Ackerman L, Alvarado JM, Doyle AG. J. Am. Chem. Soc. 2018; 140: 14059
    • 43d Sun Z, Kumagai N, Shibasaki M. Org. Lett. 2017; 19: 3727
    • 43e Shen Y, Gu Y, Martin R. J. Am. Chem. Soc. 2018; 140: 12200
    • 43f Santos MS, Corrêa AG, Paixo MW, Knig B. Adv. Synth. Catal. 2020; 362: 2367
    • 43g Zhang L, Si X, Yang Y, Zimmer M, Witzel S, Sekine K, Rudolph M, Hashmi AS. Angew. Chem. Int. Ed. 2019; 58: 1823
    • 44a Wan M, Meng Z, Lou H, Liu L. Angew. Chem. Int. Ed. 2014; 53: 13845
    • 44b Wang G, Xin X, Wang Z, Lu G, Ma Y, Liu L. Nat. Commun. 2019; 10: 559
    • 45a Shi W, Cao L, Zhang H, Zhou X, An B, Lin Z, Dai R, Li J, Wang C, Lin W. Angew. Chem. Int. Ed. 2017; 56: 9704
    • 45b Ausavasukhi A, Sooknoi T. Green Chem. 2015; 17: 435
    • 45c Schax F, Bill E, Herwig C, Limberg C. Angew. Chem. Int. Ed. 2014; 53: 12741
    • 45d Sagadevan A, Hwang KC, Su M.-D. Nat. Commun. 2017; 8: 1812
    • 45e Reetz MT, Töllner T. Tetrahedron Lett. 1995; 36: 9461
    • 45f Zhang S, Wang H, Li M, Han J, Liu X, Gong J. Chem. Sci. 2017; 8: 4489
    • 45g Guo H, Zhu C, Li J, Xu G, Sun J. Adv. Synth. Catal. 2014; 356: 2801