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Maiti, D. : 2023 Science of Synthesis, 2023/4: Cross-Dehydrogenative Coupling DOI: 10.1055/sos-SD-240-00041
Cross-Dehydrogenative Coupling

9 (Het)Arene/Alkane Cross-Dehydrogenative Coupling for C(sp2)—C(sp3) Bond Formation

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Editor: Maiti, D. 

Authors: Adak, L. ; Ali, W.; Aravindan, N.; Arun, V. ; Baidya, M. ; Besset, T. ; Brocksom, T. J. ; Chen, T. ; Chowdhury, D.; de Oliveira, K. T. ; De Sarkar, S. ; Escudero, J. ; Faisca Phillips, A. M. ; Fukuta, T.; Ghosh, S. ; Ghosh, T.; Guedes da Silva, M. F. C. ; Guin, S.; Han, L.-B. ; Huang, C.-Y. ; Iwasaki, T. ; Jeganmohan, M. ; Jha, N. ; Kakiuchi, F. ; Kambe, N.; Kanai, M. ; Kang, H. ; Kapur, M. ; Khandelia, T. ; Kochi, T. ; Koner, M.; Li, C.; Li, C.-J. ; Li, X. ; Logeswaran, R.; Maes, B. U. W. ; Maiti, D. ; Martins, G. M. ; Miyabe, H. ; Patel, B. K. ; Pombeiro, A. J. L. ; Ranu, B. C. ; Saha, S. K. ; Sambiagio, C. ; Silva, R. C. ; Song, Q. ; Zimmer, G. C. 

Title: Cross-Dehydrogenative Coupling

Print ISBN: 9783132455245; Online ISBN: 9783132455269; Book DOI: 10.1055/b000000640

1st edition © 2023. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: 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.

Type: Multivolume Edition

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Abstract

Introduction of alkyl groups onto arenes and hetarenes is a fundamental modification of (het)arenes and can exert significant effects on their physical, chemical, and/or biological properties. Among alkylation reactions, the cross-dehydrogenative coupling of (het)arenes with hydrocarbons through double C—H bond cleavage is a straightforward synthetic method that avoids prefunctionalization of the substrate(s). This review provides an overview of the alkylation of (het)arenes, including arenes, perfluoroarenes, and nitrogen, oxygen, and sulfur heterocycles, by hydrocarbons via cross-dehydrogenative coupling.

Key words

cross-dehydrogenative coupling - alkylation - arylation - catalysis - carbon–carbon bond formation - cross-coupling reactions - oxidation - arenes - pyridines - quinolines - indoles - pyrroles - benzimidazoles - benzothiazoles - nucleosides - coumarins - furans - thiophenes - benzothiophenes
 
  • 1 Li C.-J. Acc. Chem. Res. 2009; 42: 335
    PubMed
  • 2 Scheuermann CJ. Chem.–Asian J. 2010; 5: 436
    PubMed
  • 3 Liu C, Zhang H, Shi W, Lei A. Chem. Rev. 2011; 111: 1780
    PubMed
  • 4 Girard SA, Knauber T, Li C.-J. Angew. Chem. Int. Ed. 2014; 53: 74
    PubMed
  • 5 Varun BV, Dhineshkumar J, Bettadapur KR, Siddaraju Y, Alagiri K, Prabhu KR. Tetrahedron Lett. 2017; 58: 803
  • 6 Batra A, Singh KN. Eur. J. Org. Chem. 2020; 6676
  • 7 Hu R.-M, Lai Y.-H, Xu D.-Z. Synlett 2020; 31: 1753
  • 8 Afsina CMA, Aneeja T, Neetha M, Anilkumar G. Eur. J. Org. Chem. 2021; 1776
  • 9 Singh P, Mritunjay Mritunjay. Asian J. Org. Chem. 2021; 10: 964
  • 10 Peng K, Dong Z.-B. Adv. Synth. Catal. 2021; 363: 1185
  • 11 Tian T, Li Z, Li C.-J. Green Chem. 2021; 23: 6789
  • 12 Zhang Z, Chen P, Liu G. Chem. Soc. Rev. 2022; 51: 1640
    PubMed
  • 13 Deng G, Zhao L, Li C.-J. Angew. Chem. Int. Ed. 2008; 47: 6278
    PubMed
  • 14 Guin S, Rout SK, Banerjee A, Nandi S, Patel BK. Org. Lett. 2012; 14: 5294
    PubMed
  • 15 Li Q, Hu W, Hu R, Lu H, Li G. Org. Lett. 2017; 19: 4676
    PubMed
  • 16 Jia Y.-X, Kündig EP. Angew. Chem. Int. Ed. 2009; 48: 1636
    PubMed
  • 17 Perry A, Taylor RJK. Chem. Commun. (Cambridge) 2009; 3249
    PubMed
  • 18 Pugh DS, Klein JEMN, Perry A, Taylor RJK. Synlett 2010; 934
  • 19 Klein JEMN, Perry A, Pugh DS, Taylor RJK. Org. Lett. 2010; 12: 3446
    PubMed
  • 20 Ghosh S, De S, Kakde BN, Bhunia S, Adhikary A, Bisai A. Org. Lett. 2012; 14: 5864
    PubMed
  • 21 Kumar N, Ghosh S, Bhunia S, Bisai A. Beilstein J. Org. Chem. 2016; 12: 1153
    PubMed
  • 22 Donald JR, Taylor RJK, Petersen WF. J. Org. Chem. 2017; 82: 11288
    PubMed
  • 23 Zhou S.-L, Guo L.-N, Wang S, Duan X.-H. Chem. Commun. (Cambridge) 2014; 50: 3589
    PubMed
  • 24 Guo X, Li C.-J. Org. Lett. 2011; 13: 4977
    PubMed
  • 25 Li Y.-Z, Li B.-J, Lu X.-Y, Lin S, Shi Z.-J. Angew. Chem. Int. Ed. 2009; 48: 3817
    PubMed
  • 26 Spencer ARA, Grainger R, Panigrahi A, Lepper TJ, Bentkowska K, Larrosa I. Chem. Commun. (Cambridge) 2020; 56: 14479
    PubMed
  • 27 Tang Z, Wang Z, Peng Z, Yang Q, Yin S.-F, Qiu R. J. Org. Chem. 2021; 86: 2965
    PubMed
  • 28 Wu H.-R, Huang H.-Y, Ren C.-L, Liu L, Wang D, Li C.-J. Chem.–Eur. J. 2015; 21: 16744
    PubMed
  • 29 Huo C, Dong J, Su Y, Tang J, Chen F. Chem. Commun. (Cambridge) 2016; 52: 13341
    PubMed
  • 30 Yip K.-T, Nimje RY, Leskinen MV, Pihko PM. Chem.–Eur. J. 2012; 18: 12590
    PubMed
  • 31 Dhineshkumar J, Lamani M, Alagiri K, Prabhu KR. Org. Lett. 2013; 15: 1092
    PubMed
  • 32 Chen W, Wilde RG, Seidel D. Org. Lett. 2014; 16: 730
    PubMed
  • 33 Li Z, Bohle DS, Li C.-J. Proc. Natl. Acad. Sci. U. S. A. 2006; 103: 8928
    PubMed
  • 34 Zhang L, Peng C, Zhao D, Wang Y, Fu H.-J, Shen Q, Li J.-X. Chem. Commun. (Cambridge) 2012; 48: 5928
    PubMed
  • 35 Shirakawa E, Uchiyama N, Hayashi T. J. Org. Chem. 2011; 76: 25
    PubMed
  • 36 Shirakawa E, Yoneda T, Moriya K, Ota K, Uchiyama N, Nishikawa R, Hayashi T. Chem. Lett. 2011; 40: 1041
  • 37 Dai C, Meschini F, Narayanam JMR, Stephenson CRJ. J. Org. Chem. 2012; 77: 4425
    PubMed
  • 38 Ghobrial M, Harhammer K, Mihovilovic MD, Schnürch M. Chem. Commun. (Cambridge) 2010; 46: 8836
    PubMed
  • 39 Park SJ, Price JR, Todd MH. J. Org. Chem. 2012; 77: 949
    PubMed
  • 40 Feng G, Sun C, Xin X, Wan R, Liu L. Tetrahedron Lett. 2019; 60: 1547
  • 41 Li F, Meng Z, Hua J, Li W, Lou H, Liu L. Org. Biomol. Chem. 2015; 13: 5710
    PubMed
  • 42 Ueno R, Shirakawa E. Org. Biomol. Chem. 2014; 12: 7469
    PubMed
  • 43 Xie W, Heo J, Kim D, Chang S. J. Am. Chem. Soc. 2020; 142: 7487
    PubMed
  • 44 Xie W, Kim D, Chang S. J. Am. Chem. Soc. 2020; 142: 20588
    PubMed
  • 45 Liu H.-C, Li Y, Gong X.-P, Niu Z.-J, Wang Y.-Z, Li M, Shi W.-Y, Zhang Z, Liang Y.-M. Org. Lett. 2021; 23: 2693
    PubMed
  • 46 Minisci F, Vismara E, Fontana F. Heterocycles 1989; 28: 489
  • 47 Deng G, Ueda K, Yanagisawa S, Itami K, Li C.-J. Chem.–Eur. J. 2009; 15: 333
    PubMed
  • 48 Fang L, Chen L, Yu J, Wang L. Eur. J. Org. Chem. 2015; 1910
  • 49 Deng G, Li C.-J. Org. Lett. 2009; 11: 1171
    PubMed
  • 50 Antonchick AP, Burgmann L. Angew. Chem. Int. Ed. 2013; 52: 3267
    PubMed
  • 51 Huang C.-Y, Li J, Li C.-J. Nat. Commun. 2021; 12: 4010
    PubMed
  • 52 Huang C, Wang J.-H, Qiao J, Fan X.-W, Chen B, Tung C.-H, Wu L.-Z. J. Org. Chem. 2019; 84: 12904
    PubMed
  • 53 Tian H, Yang H, Tian C, An G, Li G. Org. Lett. 2020; 22: 7709
    PubMed
  • 54 Huang C.-Y, Li J, Liu W, Li C.-J. Chem. Sci. 2019; 10: 5018
    PubMed
  • 55 Shao X, Wu X, Wu S, Zhu C. Org. Lett. 2020; 22: 7450
    PubMed
  • 56 Zhao H, Jin J. Org. Lett. 2019; 21: 6179
    PubMed
  • 57 Xu P, Chen P.-Y, Xu H.-C. Angew. Chem. Int. Ed. 2020; 59: 14275
    PubMed
  • 58 Lee W, Jung S, Kim M, Hong S. J. Am. Chem. Soc. 2021; 143: 3003
    PubMed
  • 59 Kianmehr E, Fardpour M, Khan KM. Eur. J. Org. Chem. 2017; 2661
  • 60 Jin J, MacMillan DWC. Angew. Chem. Int. Ed. 2015; 54: 1565
    PubMed
  • 61 Ambala S, Thatikonda T, Sharma S, Munagala G, Yempalla KR, Vishwakarma RA, Singh PP. Org. Biomol. Chem. 2015; 13: 11341
    PubMed
  • 62 Huang H, Strater ZM, Lambert TH. J. Am. Chem. Soc. 2020; 142: 1698
    PubMed
  • 63 Correia CA, Yang L, Li C.-J. Org. Lett. 2011; 13: 4581
    PubMed
  • 64 Devari S, Shah BA. Chem. Commun. (Cambridge) 2016; 52: 1490
    PubMed
  • 65 Wang S, Fan Y, Zhao H, Wang J, Zhang S, Wang W. Synlett 2019; 30: 2096
  • 66 Xu J, Cai H, Shen J, Shen C, Wu J, Zhang P, Liu X. J. Org. Chem. 2021; 86: 17816
    PubMed
  • 67 Quattrini MC, Fujii S, Yamada K, Fukuyama T, Ravelli D, Fagnoni M, Ryu I. Chem. Commun. (Cambridge) 2017; 53: 2335
    PubMed
  • 68 Li G.-X, Hu X, He G, Chen G. ACS Catal. 2018; 8: 11847
  • 69 Liang X.-A, Niu L, Wang S, Liu J, Lei A. Org. Lett. 2019; 21: 2441
    PubMed
  • 70 Ravelli D, Fagnoni M, Fukuyama T, Nishikawa T, Ryu I. ACS Catal. 2018; 8: 701
  • 71 Niu L, Liu J, Liang X.-A, Wang S, Lei A. Nat. Commun. 2019; 10: 467
    PubMed
  • 72 Zhan F, Zhang W, Zhao H. Synthesis 2020; 52: 1007
  • 73 Xu W, Wu M, Yoshikai N. Synthesis 2021; 53: 3144
  • 74 Hu A, Guo J.-J, Pan H, Zuo Z. Science (Washington, D. C.) 2018; 361: 668
    PubMed
  • 75 Samanta S, Hajra A. J. Org. Chem. 2019; 84: 4363
    PubMed
  • 76 Dong J, Xia Q, Lv X, Yan C, Song H, Liu Y, Wang Q. Org. Lett. 2018; 20: 5661
    PubMed
  • 77 Guo S, Li Y, Wang Y, Guo X, Meng X, Chen B. Adv. Synth. Catal. 2015; 357: 950
  • 78 Mo H, Bao W. Adv. Synth. Catal. 2009; 351: 2845
  • 79 Sonobe T, Oisaki K, Kanai M. Chem. Sci. 2012; 3: 3249
  • 80 Liu P, Zhou C.-Y, Xiang S, Che C.-M. Chem. Commun. (Cambridge) 2010; 46: 2739
    PubMed
  • 81 Li Z, Li C.-J. J. Am. Chem. Soc. 2005; 127: 6968
    PubMed
  • 82 Han X, He X, Sun L, Han X, Zhan W, Xu J, Wang X, Chen J. ACS Catal. 2018; 8: 3348
  • 83 Alagiri K, Kumara GSR, Prabhu KR. Chem. Commun. (Cambridge) 2011; 47: 11787
    PubMed
  • 84 Wu C.-J, Zhong J.-J, Meng Q.-Y, Lei T, Gao X.-W, Tung C.-H, Wu L.-Z. Org. Lett. 2015; 17: 884
    PubMed
  • 85 Zhong J.-J, Meng Q.-Y, Wang G.-X, Liu Q, Chen B, Feng K, Tung C.-H, Wu L.-Z. Chem.–Eur. J. 2013; 19: 6443
    PubMed
  • 86 Meng Q.-Y, Zhong J.-J, Liu Q, Gao X.-W, Zhang H.-H, Lei T, Li Z.-J, Feng K, Chen B, Tung C.-H, Wu L.-Z. J. Am. Chem. Soc. 2013; 135: 19052
    PubMed
  • 87 Girish YR, Jaiswal K, Prakash P, De M. Catal. Sci. Technol. 2019; 9: 1201
  • 88 Ueda H, Yoshida K, Tokuyama H. Org. Lett. 2014; 16: 4194
    PubMed
  • 89 Ohta M, Quick MP, Yamaguchi J, Wünsch B, Itami K. Chem.–Asian J. 2009; 4: 1416
    PubMed
  • 90 Yang F, Li J, Xie J, Huang Z.-Z. Org. Lett. 2010; 12: 5214
    PubMed
  • 91 Wang M.-Z, Zhou C.-Y, Wong M.-K, Che C.-M. Chem.–Eur. J. 2010; 16: 5723
    PubMed
  • 92 Yang Q, Choy PY, Wu Y, Fan B, Kwong FY. Org. Biomol. Chem. 2016; 14: 2608
    PubMed
  • 93 Jin L.-K, Wan L, Feng J, Cai C. Org. Lett. 2015; 17: 4726
    PubMed
  • 94 Guo X, Pan S, Liu J, Li Z. J. Org. Chem. 2009; 74: 8848
    PubMed
  • 95 Wang C, Gong M, Huang M, Li Y, Kim JK, Wu Y. Tetrahedron 2016; 72: 7931
  • 96 Liégault B, Fagnou K. Organometallics 2008; 27: 4841
  • 97 Correa A, Fiser B, Gómez-Bengoa E. Chem. Commun. (Cambridge) 2015; 51: 13365
    PubMed
  • 98 Xia R, Niu H.-Y, Qu G.-R, Guo H.-M. Org. Lett. 2012; 14: 5546
    PubMed
  • 99 Wang X, Lei B, Ma L, Zhu L, Zhang X, Zuo H, Zhuang D, Li Z. Chem.–Asian J. 2017; 12: 2799
    PubMed
  • 100 Wang J, Li J, Huang J, Zhu Q. J. Org. Chem. 2016; 81: 3017
    PubMed
  • 101 Zhang Y, Teuscher KB, Ji H. Chem. Sci. 2016; 7: 2111
    PubMed
  • 102 Capaldo L, Quadri LL, Merli D, Ravelli D. Chem. Commun. (Cambridge) 2021; 57: 4424
    PubMed
  • 103 Huang L, Niu T, Wu J, Zhang Y. J. Org. Chem. 2011; 76: 1759
    PubMed
  • 104 Zhang R, Jin S, Liu Q, Lin S, Yan Z. J. Org. Chem. 2018; 83: 13030
    PubMed
  • 105 Niu B, Zhao W, Ding Y, Bian Z, Pittman Jr CU, Zhou A, Ge H. J. Org. Chem. 2015; 80: 7251
    PubMed
  • 106 Dian L, Zhao H, Zhang-Negrerie D, Du Y. Adv. Synth. Catal. 2016; 358: 2422
  • 107 Zhu Y, Wei Y. Chem. Sci. 2014; 5: 2379
  • 108 Zhou S.-L, Guo L.-N, Duan X.-H. Eur. J. Org. Chem. 2014; 8094
  • 109 Banerjee A, Santra SK, Khatun N, Ali W, Patel BK. Chem. Commun. (Cambridge) 2015; 51: 15422
    PubMed
  • 110 Wang C, Mi X, Li Q, Li Y, Huang M, Zhang J, Wu Y, Wu Y. Tetrahedron 2015; 71: 6689
  • 111 Alagiri K, Devadig P, Prabhu KR. Chem.–Eur. J. 2012; 18: 5160
    PubMed
  • 112 Narayan R, Antonchick AP. Chem.–Eur. J. 2014; 20: 4568
    PubMed
  • 113 Sudo Y, Yamaguchi E, Itoh A. Org. Lett. 2017; 19: 1610
    PubMed