Yoshikai, N. : 2023 Science of Synthesis, 2022/5: Base-Metal Catalysis 1 DOI: 10.1055/sos-SD-238-00251
Base-Metal Catalysis 1

1.13 Nickel-Catalyzed Cross Coupling Involving Alkenes

Weitere Informationen

Buch

Herausgeber: Yoshikai, N.

Autoren: Chatani, N. ; Chemler, S. R. ; Chen, P. ; Dai, H.-X. ; Delcaillau, T.; Fujihara, T. ; Huang, J. ; Iwabuchi, Y. ; Kennedy-Ellis, J. J. ; Ko, C.; Koh, M. J. ; Lee, B. C.; Li, Y.; Lin, L.; Liu, G. ; Ma, D. ; Morandi, B. ; Nakao, Y. ; Ouyang, Y. ; Pang, X.; Qing, F.-L. ; Ren, Y. ; Sasano, Y. ; Shang, Y. ; Shou, J.-Y.; Shu, X.-Z. ; Su, W. ; Tobisu, M. ; Wang, C. ; Xiong, T. ; Xu, H.; Yang, F.; Yoshida, T.; Zhu, S.

Titel: Base-Metal Catalysis 1

Print ISBN: 9783132453807; Online ISBN: 9783132453821; Buch-DOI: 10.1055/b000000441

Fachgebiete: Organische Chemie;Chemische Reaktionen, Katalyse;Organometallchemie;Chemische Labormethoden, Stöchiometrie

Science of Synthesis Reference Libraries



Übergeordnete Publikation

Titel: Science of Synthesis

DOI: 10.1055/b-00000101

Reihenherausgeber: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Typ: Mehrbändiges Werk

 


Abstract

Nickel-catalyzed functionalization of alkenes to give value-added products in a manner that is rapid, selective, and modular has resulted in tremendous advances in synthetic chemistry. Great progress has been achieved in nickel-catalyzed (migratory) hydrofunctionalization and difunctionalization of alkenes over the past few years. In the first half of this chapter, nickel-catalyzed (migratory) hydrofunctionalization of alkenes is described. The second half details nickel-catalyzed difunctionalization of alkenes. Both reductive and redox-neutral reactions are discussed.

 
  • 1 Tasker SZ, Standley EA, Jamison TF. Nature (London) 2014; 509: 299
  • 2 Fu GC. ACS Cent. Sci. 2017; 3: 692
  • 3 Poremba KE, Dibrell SE, Reisman SE. ACS Catal. 2020; 10: 8237
  • 4 Wang X.-X, Lu X, Li Y, Wang J.-W, Fu Y. Sci. China Chem. 2020; 63: 1586
  • 5 He Y, Chen J, Jiang X, Zhu S. Chin. J. Chem. 2022; 40: 651
  • 6 Janssen-Müller D, Sahoo B, Sun S.-Z, Martin R. Isr. J. Chem. 2020; 60: 195
  • 7 Luo Y.-C, Xu C, Zhang X. Chin. J. Chem. 2020; 38: 1371
  • 8 Liu RY, Buchwald SL. Acc. Chem. Res. 2020; 53: 1229
  • 9 Crossley SWM, Obradors C, Martinez RM, Shenvi RA. Chem. Rev. 2016; 116: 8912
  • 10 Chen J, Guo J, Lu Z. Chin. J. Chem. 2018; 36: 1075
  • 11 Ning Y, Ohwada T, Chen F.-E. Green Synth. Catal. 2021; 2: 247
  • 12 Lu X, Xiao B, Zhang Z, Gong T, Su W, Yi J, Fu Y, Liu L. Nat. Commun. 2016; 7: 11129
  • 13 He Y, Cai Y, Zhu S. J. Am. Chem. Soc. 2017; 139: 1061
  • 14 Chen F, Chen K, Zhang Y, He Y, Wang Y.-M, Zhu S. J. Am. Chem. Soc. 2017; 139: 13929
  • 15 Shevick SL, Obradors C, Shenvi RA. J. Am. Chem. Soc. 2018; 140: 12056
  • 16 Zhang Y, Han B, Zhu S. Angew. Chem. Int. Ed. 2019; 58: 13860
  • 17 Bera S, Hu X. Angew. Chem. Int. Ed. 2019; 58: 13854
  • 18 Kumar GS, Peshkov A, Brzozowska A, Nikolaienko P, Zhu C, Rueping M. Angew. Chem. Int. Ed. 2020; 59: 6513
  • 19 He Y, Liu C, Yu L, Zhu S. Angew. Chem. Int. Ed. 2020; 59: 21530
  • 20 Cuesta-Galisteo S, Schörgenhumer J, Wei X, Merino E, Nevado C. Angew. Chem. Int. Ed. 2021; 60: 1605
  • 21 He Y, Song H, Chen J, Zhu S. Nat. Commun. 2021; 12: 638
  • 22 He Y, Tao R, Zhu S. Synlett 2022; 33: 224
  • 23 Zhang Y, Ma J, Chen J, Meng L, Liang Y, Zhu S. Chem 2021; 7: 3171
  • 24 Liu J, Gong H, Zhu S. Angew. Chem. Int. Ed. 2021; 60: 4060
  • 25 Jiang X, Han B, Xue Y, Duan M, Gui Z, Wang Y, Zhu S. Nat. Commun. 2021; 12: 3792
  • 26 Zhou F, Zhu J, Zhang Y, Zhu S. Angew. Chem. Int. Ed. 2018; 57: 4058
  • 27 Sun S.-Z, Börjesson M, Martin-Montero R, Martin R. J. Am. Chem. Soc. 2018; 140: 12765
  • 28 Wang Z, Yin H, Fu GC. Nature (London) 2018; 563: 379
  • 29 Zhou F, Zhang Y, Xu X, Zhu S. Angew. Chem. Int. Ed. 2019; 58: 1754
  • 30 He S.-J, Wang J.-W, Li Y, Xu Z.-Y, Wang X.-X, Lu X, Fu Y. J. Am. Chem. Soc. 2020; 142: 214
  • 31 Yang Z.-P, Fu GC. J. Am. Chem. Soc. 2020; 142: 5870
  • 32 Bera S, Mao R, Hu X. Nat. Chem. 2021; 13: 270
  • 33 Wang J.-W, Li Y, Nie W, Chang Z, Yu Z.-A, Zhao Y.-F, Lu X, Fu Y. Nat. Commun. 2021; 12: 1313
  • 34 Qian D, Bera S, Hu X. J. Am. Chem. Soc. 2021; 143: 1959
  • 35 Wang S, Zhang J.-X, Zhang T.-Y, Meng H, Chen B.-H, Shu W. Nat. Commun. 2021; 12: 2771
  • 36 Shi L, Xing L.-L, Hu W.-B, Shu W. Angew. Chem. Int. Ed. 2021; 60: 1599
  • 37 Zhou F, Zhu S. ACS Catal. 2021; 11: 8766
  • 38 Juliá-Hernández F, Moragas T, Cornella J, Martin R. Nature (London) 2017; 545: 84
  • 39 Gaydou M, Moragas T, Juliá-Hernández F, Martin R. J. Am. Chem. Soc. 2017; 139: 12161
  • 40 He J, Song P, Xu X, Zhu S, Wang Y. ACS Catal. 2019; 9: 3253
  • 41 Chen J, Zhu S. J. Am. Chem. Soc. 2021; 143: 14089
  • 42 Xiao J, He Y, Ye F, Zhu S. Chem 2018; 4: 1645
  • 43 Zhang Y, He J, Song P, Wang Y, Zhu S. CCS Chem. 2020; 2: 2259
  • 44 Jeon J, Lee C, Seo H, Hong S. J. Am. Chem. Soc. 2020; 142: 20470
  • 45 Lee C, Seo H, Jeon J, Hong S. Nat. Commun. 2021; 12: 5657
  • 46 Du B, Ouyang Y, Chen Q, Yu W.-Y. J. Am. Chem. Soc. 2021; 143: 14962
  • 47 Lyu X, Zhang J, Kim D, Seo S, Chang S. J. Am. Chem. Soc. 2021; 143: 5867
  • 48 Meng L, Yang J, Duan M, Wang Y, Zhu S. Angew. Chem. Int. Ed. 2021; 60: 23584
  • 49 Zhang Y, Xu X, Zhu S. Nat. Commun. 2019; 10: 1752
  • 50 Xiao L.-J, Cheng L, Feng W.-M, Li M.-L, Xie J.-H, Zhou Q.-L. Angew. Chem. Int. Ed. 2018; 57: 461
  • 51 Lv X.-Y, Fan C, Xiao L.-J, Xie J.-H, Zhou Q.-L. CCS Chem. 2019; 1: 328
  • 52 Chen Y.-G, Shuai B, Xu X.-T, Li Y.-Q, Yang Q.-L, Qiu H, Zhang K, Fang P, Mei T.-S. J. Am. Chem. Soc. 2019; 141: 3395
  • 53 He Y, Liu C, Yu L, Zhu S. Angew. Chem. Int. Ed. 2020; 59: 9186
  • 54 Li Y, Luo Y, Peng L, Li Y, Zhao B, Wang W, Pang H, Deng Y, Bai R, Lan Y, Yin G. Nat. Commun. 2020; 11: 417
  • 55 Tran G, Shao W, Mazet C. J. Am. Chem. Soc. 2019; 141: 14814
  • 56 Li Y, Wu D, Cheng H.-G, Yin G. Angew. Chem. Int. Ed. 2020; 59: 7990
  • 57 Liu Z, Gao Y, Zeng T, Engle KM. Isr. J. Chem. 2020; 60: 219
  • 58 Badir SO, Molander GA. Chem 2020; 6: 1327
  • 59 Qi X, Diao T. ACS Catal. 2020; 10: 8542
  • 60 Ping Y, Kong W. Synthesis 2020; 52: 979
  • 61 Derosa J, Apolinar O, Kang T, Tran VT, Engle KM. Chem. Sci 2020; 11: 4287
  • 62 Zhu S, Zhao X, Li H, Chu L. Chem. Soc. Rev. 2021; 50: 10836
  • 63 Wickham LM, Giri R. Acc. Chem. Res. 2021; 54: 3415
  • 64 Logan KM, Sardini SR, White SD, Brown MK. J. Am. Chem. Soc. 2018; 140: 159
  • 65 Sardini SR, Lambright AL, Trammel GL, Omer HM, Liu P, Brown MK. J. Am. Chem. Soc. 2019; 141: 9391
  • 66 Trammel GL, Kuniyil R, Crook PF, Liu P, Brown MK. J. Am. Chem. Soc. 2021; 143: 16502
  • 67 Wang W, Ding C, Li Y, Li Z, Li Y, Peng L, Yin G. Angew. Chem. Int. Ed. 2019; 58: 4612
  • 68 Li Y, Pang H, Wu D, Li Z, Wang W, Wei H, Fu Y, Yin G. Angew. Chem. Int. Ed. 2019; 58: 8872
  • 69 Wang W, Ding C, Yin G. Nat. Catal. 2020; 3: 951
  • 70 Catellani M, Chiusoli GP, Mari A. J. Organomet. Chem. 1984; 275: 129
  • 71 Cong H, Fu GC. J. Am. Chem. Soc. 2014; 136: 3788
  • 72 Walker JA, Vickerman KL, Humke JN, Stanley LM. J. Am. Chem. Soc. 2017; 139: 10228
  • 73 Wang K, Ding Z, Zhou Z, Kong W. J. Am. Chem. Soc. 2018; 140: 12364
  • 74 Fan P, Lan Y, Zhang C, Wang C. J. Am. Chem. Soc. 2020; 142: 2180
  • 75 Wang H, Liu C.-F, Martin RT, Gutierrez O, Koh MJ. Nat. Chem. 2022; 14: 188
  • 76 Chierchia M, Law C, Morken JP. Angew. Chem. Int. Ed. 2017; 56: 11870
  • 77 Lovinger GJ, Morken JP. J. Am. Chem. Soc. 2017; 139: 17293
  • 78 Gu J.-W, Min Q.-Q, Yu L.-C, Zhang X. Angew. Chem. Int. Ed. 2016; 55: 12270
  • 79 García-Domínguez A, Li Z, Nevado C. J. Am. Chem. Soc. 2017; 139: 6835
  • 80 Shu W, García-Domínguez A, Quirós MT, Mondal R, Cárdenas DJ, Nevado C. J. Am. Chem. Soc. 2019; 141: 13812
  • 81 Tu H.-Y, Wang F, Huo L, Li Y, Zhu S, Zhao X, Li H, Qing F.-L, Chu L. J. Am. Chem. Soc. 2020; 142: 9604
  • 82 Wei X, Shu W, García-Domínguez A, Merino E, Nevado C. J. Am. Chem. Soc. 2020; 142: 13515
  • 83 Qin T, Cornella J, Li C, Malins LR, Edwards JT, Kawamura S, Maxwell BD, Eastgate MD, Baran PS. Science (Washington, D. C.) 2016; 352: 801
  • 84 Zheng S, Chen Z, Hu Y, Xi X, Liao Z, Li W, Yuan W. Angew. Chem. Int. Ed. 2020; 59: 17910
  • 85 Sun S.-Z, Duan Y, Mega RS, Somerville RJ, Martin R. Angew. Chem. Int. Ed. 2020; 59: 4370
  • 86 García-Domínguez A, Mondal R, Nevado C. Angew. Chem. Int. Ed. 2019; 58: 12286
  • 87 Campbell MW, Compton JS, Kelly CB, Molander GA. J. Am. Chem. Soc. 2019; 141: 20069
  • 88 Guo L, Yuan M, Zhang Y, Wang F, Zhu S, Gutierrez O, Chu L. J. Am. Chem. Soc. 2020; 142: 20390
  • 89 He J, Xue Y, Zhang C, Wang Y, Zhu S. Angew. Chem. Int. Ed. 2020; 59: 2328
  • 90 van der Puyl VA, Derosa J, Engle KM. ACS Catal. 2019; 9: 224
  • 91 Xie L, Wang S, Zhang L, Zhao L, Luo C, Mu L, Wang X, Wang C. Nat. Commun. 2021; 12: 6280
  • 92 Kang T, Kim N, Cheng PT, Zhang H, Foo K, Engle KM. J. Am. Chem. Soc. 2021; 143: 13962