Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis 2019; 51(03): 643-663
DOI: 10.1055/s-0037-1610852
DOI: 10.1055/s-0037-1610852
short review
Recent Developments in Palladium-Catalysed Non-Directed C–H Bond Activation in Arenes
This work was supported by an EU COST ACTION CA15106 (CHAOS) STSM grant and a UiS Research Mobility grant.
Further Information
Publication History
Received: 17 September 2018
Accepted after revision: 17 October 2018
Publication Date:
08 January 2019 (online)
Abstract
Over the past decades, organic chemists have focussed on developing new approaches to directed C–H functionalisations, where the site selectivity is steered by the presence of a directing group (DG). Nonetheless, in recent years, more and more non-directed strategies are being developed to circumvent the requisite directing group, making C–H functionalisations more generic. This short review focuses on the latest developments in palladium-catalysed non-directed C–H functionalisations of aromatic compounds.
1 Introduction
2 C–C Bond Formation
2.1 C–H Arylation
2.2 C–H Alkylation
2.3 C–H Alkenylation
2.4 C–H Carbonylation
3 C–Heteroatom Bond Formation
3.1 C–O Bond Formation
3.2 C–N Bond Formation
3.3 C–S Bond Formation
4 Conclusion
-
References
- 1 Arockiam PB, Bruneau C, Dixneuf PH. Chem. Rev. 2012; 112: 5879
- 2 Wencel-Delord J, Glorius F. Nat. Chem. 2013; 5: 369
- 3a Seregin IV, Gevorgyan V. Chem. Soc. Rev. 2007; 36: 1173
- 3b Engle KM, Mei T.-S, Wasa M, Yu J.-Q. Acc. Chem. Res. 2012; 45: 788
- 3c Leow D, Li G, Mei T.-S, Yu J.-Q. Nature 2012; 486: 518
- 3d Wan L, Dastbaravardeh N, Li G, Yu J.-Q. J. Am. Chem. Soc. 2013; 135: 18056
- 3e Luo J, Preciado S, Larrosa I. J. Am. Chem. Soc. 2014; 136: 4109
- 3f Chen Z, Wang B, Zhang J, Yu W, Liu Z, Zhang Y. Org. Chem. Front. 2015; 2: 1107
- 3g Yang J. Org. Biomol. Chem. 2015; 13: 1930
- 3h Liu X.-H, Park H, Hu J.-H, Hu Y, Zhang Q.-L, Wang B.-L, Sun B, Yeung K.-S, Zhang F.-L, Yu J.-Q. J. Am. Chem. Soc. 2017; 139: 888
- 3i Fairlamb IJ. S, Kapdi AR. In Strategies for Palladium-Catalyzed Non-Directed and Directed C–H Bond Functionalization . Kapdi AR, Maiti D. Elsevier; Amsterdam: 2017: 9
- 3j Yang G, Zhu D, Wang P, Tang RY, Yu JQ. Chem. Eur. J. 2018; 24: 3434
- 3k Sambiagio C, Schönbauer D, Blieck R, Dao-Huy T, Pototschnig G, Schaaf P, Wiesinger T, Zia MF, Wencel-Delord J, Besset T, Maes BU. W, Schnürch M. Chem. Soc. Rev. 2018; 47: 6603
- 4 Hartwig JF, Larsen MA. ACS Cent. Sci. 2016; 2: 281
- 5
Kuhl N,
Hopkinson MN,
Wencel-Delord J,
Glorius F.
Angew. Chem. Int. Ed. 2012; 51: 10236
MissingFormLabel
- 6a Yamaguchi J, Itami K. In Metal-Catalyzed Cross-Coupling Reactions and More . de Meijere A, Bräse S, Oestreich M. Wiley-VCH; Weinheim: 2013: 1315
- 6b Alberico D, Scott ME, Lautens M. Chem. Rev. 2007; 107: 174
- 7 Yang Y, Lan J, You J. Chem. Rev. 2017; 117: 8787
- 8 Hickman AJ, Sanford MS. ACS Catal. 2011; 1: 170
- 9 Storr TE, Greaney MF. Org. Lett. 2013; 15: 1410
- 10 Luo H.-Q, Dong W, Loh T.-P. Tetrahedron Lett. 2013; 54: 2833
- 11 Luan Y.-X, Zhang T, Yao W.-W, Lu K, Kong L.-Y, Lin Y.-T, Ye M. J. Am. Chem. Soc. 2017; 139: 1786
- 12 Kim J, Hong SH. ACS Catal. 2017; 7: 3336
- 13 Ricci P, Krämer K, Cambeiro XC, Larrosa I. J. Am. Chem. Soc. 2013; 135: 13258
- 14 Whitaker D, Batuecas M, Ricci P, Larrosa I. Chem. Eur. J. 2017; 23: 12763
- 15 Ricci P, Krämer K, Larrosa I. J. Am. Chem. Soc. 2014; 136: 18082
- 16 Yan T, Zhao L, He M, Soulé J.-F, Bruneau C, Doucet H. Adv. Synth. Catal. 2014; 356: 1586
- 17 He M, Soulé J.-F, Doucet H. ChemCatChem 2015; 7: 2130
- 18 Hfaiedh A, Ben Ammar H, Soule J.-F, Doucet H. Org. Biomol. Chem. 2017; 15: 7447
- 19 Tang ML, Reichardt AD, Miyaki N, Stoltenberg RM, Bao Z. J. Am. Chem. Soc. 2008; 130: 6064
- 20 Liu S.-Y, Shi M.-M, Huang J.-C, Jin Z.-N, Hu X.-L, Pan J.-Y, Li H.-Y, Jen AK. Y, Chen H.-Z. J. Mater. Chem. A 2013; 1: 2795
- 21 Guo F, Han J, Mao S, Li J, Geng X, Yu J, Wang L. RSC Adv. 2013; 3: 6267
- 22 Yuan K, Soulé J.-F, Doucet H. ACS Catal. 2015; 5: 978
- 23 Miao T, Wang L. Adv. Synth. Catal. 2014; 356: 429
- 24 Zhang H.-H, Dong J, Hu Q.-S. Eur. J. Org. Chem. 2014; 1327
- 25 Wang X.-Y, Zhuang F.-D, Wang R.-B, Wang X.-C, Cao X.-Y, Wang J.-Y, Pei J. J. Am. Chem. Soc. 2014; 136: 3764
- 26 Segawa Y, Maekawa T, Itami K. Angew. Chem. Int. Ed. 2015; 54: 66
- 27a Mochida K, Kawasumi K, Segawa Y, Itami K. J. Am. Chem. Soc. 2011; 133: 10716
- 27b Kawasumi K, Mochida K, Kajino T, Segawa Y, Itami K. Org. Lett. 2012; 14: 418
- 28 Zhang Q, Kawasumi K, Segawa Y, Itami K, Scott LT. J. Am. Chem. Soc. 2012; 134: 15664
- 29 Kawasumi K, Mochida K, Segawa Y, Itami K. Tetrahedron 2013; 69: 4371
- 30 Ozaki K, Kawasumi K, Shibata M, Ito H, Itami K. Nat. Commun. 2015; 6: 6251
- 31 Shibata M, Ito H, Itami K. J. Am. Chem. Soc. 2018; 140: 2196
- 32 Zhu C, Zhao Y, Wang D, Sun W.-Y, Shi Z. Sci. Rep. 2016; 6: 33131
- 33 Yeung CS, Dong VM. Chem. Rev. 2011; 111: 1215
- 34 Li H, Liu J, Sun C.-L, Li B.-J, Shi Z.-J. Org. Lett. 2011; 13: 276
- 35 Chen F, Feng Z, He C.-Y, Wang H.-Y, Guo Y.-l, Zhang X. Org. Lett. 2012; 14: 1176
- 36 Jafarpour F, Hazrati H, Mohasselyazdi N, Khoobi M, Shafiee A. Chem. Commun. 2013; 49: 10935
- 37 Ren X, Wen P, Shi X, Wang Y, Li J, Yang S, Yan H, Huang G. Org. Lett. 2013; 15: 5194
- 38 Zhang S, Song F, Zhao D, You J. Chem. Commun. 2013; 49: 4558
- 39 Wang S, Liu W, Cen J, Liao J, Huang J, Zhan H. Tetrahedron Lett. 2014; 55: 1589
- 40 Jafarpour F, Shamsianpour M. RSC Adv. 2016; 6: 103567
- 41 Álvarez-Casao Y, van Slagmaat CA. M. R, Verzijl GK. M, Lefort L, Alsters PL, Fernández-Ibáñez M. Á. ChemCatChem 2018; 10: 2620
- 42a Alsters PL. (DSM) WO2016/008931, 2016
- 42b Alsters PL, Lefort L, van Slagmaat CA. M. R, van Summeren RP, Verzijil GK. M. (DSM) WO2017/102944, 2017
- 43 Wang D, Stahl SS. J. Am. Chem. Soc. 2017; 139: 5704
- 44 Li J, Warratz S, Zell D, De Sarkar S, Ishikawa EE, Ackermann L. J. Am. Chem. Soc. 2015; 137: 13894
- 45
Wang X.-C,
Gong W,
Fang L.-Z,
Zhu R.-Y,
Li S,
Engle KM,
Yu J.-Q.
Nature 2015; 519: 334
MissingFormLabel
- 46 Jiao Z, Lim LH, Hirao H, Zhou JS. Angew. Chem. Int. Ed. 2018; 57: 6294
- 47
Zhou L,
Lu W.
Chem. Eur. J. 2014; 20: 634
MissingFormLabel
- 48 Babu BP, Meng X, Bäckvall J.-E. Chem. Eur. J. 2013; 19: 4140
- 49 Gigant N, Bäckvall J.-E. Org. Lett. 2014; 16: 1664
- 50 Gigant N, Bäckvall J.-E. Org. Lett. 2014; 16: 4432
- 51 Gigant N, Quintin F, Bäckvall J.-E. J. Org. Chem. 2015; 80: 2796
- 52 Jones RC, Gałęzowski M, O’Shea DF. J. Org. Chem. 2013; 78: 8044
- 53 Harada S, Yano H, Obora Y. ChemCatChem 2013; 5: 121
- 54 Fujiwara Y, Moritani I, Danno S, Asano R, Teranishi S. J. Am. Chem. Soc. 1969; 91: 7166
- 55 She Z, Shi Y, Huang Y, Cheng Y, Song F, You J. Chem. Commun. 2014; 50: 13914
- 56 Jin W, Wong WT, Law GL. ChemCatChem 2014; 6: 1599
- 57 Lei Y, Qiu R, Zhang L, Xu C, Pan Y, Qin X, Li H, Xu L, Deng Y. ChemCatChem 2015; 7: 1275
- 58 Mizuta Y, Obora Y, Shimizu Y, Ishii Y. ChemCatChem 2012; 4: 187
- 59 Moghaddam FM, Pourkaveh R, Karimi A. J. Org. Chem. 2017; 82: 10635
- 60 Cong X, Tang H, Wu C, Zeng X. Organometallics 2013; 32: 6565
- 61 Ying C.-H, Yan S.-B, Duan W.-L. Org. Lett. 2014; 16: 500
- 62 Naksomboon K, Valderas C, Gómez-Martínez M, Álvarez-Casao Y, Fernández-Ibáñez M. Á. ACS Catal. 2017; 7: 6342
- 63a
Wang P,
Verma P,
Xia G,
Shi J,
Qiao JX,
Tao S,
Cheng PT. W,
Poss MA,
Farmer ME,
Yeung K.-S,
Yu J.-Q.
Nature 2017; 551: 489
MissingFormLabel
- 63b
Chen H,
Wedi P,
Meyer T,
Tavakoli G,
van Gemmeren M.
Angew. Chem. Int. Ed. 2018; 57: 2497
MissingFormLabel
- 64 Kubota A, Emmert MH, Sanford MS. Org. Lett. 2012; 14: 1760
- 65 Naksomboon K, Álvarez-Casao Y, Uiterweerd M, Westerveld N, Maciá B, Fernández-Ibáñez M. Á. Tetrahedron Lett. 2018; 59: 379
- 66 Tang R.-Y, Li G, Yu J.-Q. Nature 2014; 507: 215
- 67a Zhang X, Fan S, He C.-Y, Wan X, Min Q.-Q, Yang J, Jiang Z.-X. J. Am. Chem. Soc. 2010; 132: 4506
- 67b Li Z, Zhang Y, Liu Z.-Q. Org. Lett. 2012; 14: 74
- 68 Yu Y.-B, Fan S, Zhang X. Chem. Eur. J. 2012; 18: 14643
- 69 Steinhoff BA, Stahl SS. J. Am. Chem. Soc. 2006; 128: 4348
- 70 Wu C.-Z, He C.-Y, Huang Y, Zhang X. Org. Lett. 2013; 15: 5266
- 71 Zheng J, Breit B. Org. Lett. 2018; 20: 1866
- 72 Lian Z, Friis SD, Skrydstrup T. Chem. Commun. 2015; 51: 1870
- 73 The Chemistry of Phenols . Rappoport Z. Wiley; VCH, Weinheim: 2003
- 74 Dictionary of Natural Products . Buckingham J. University Press; Cambridge, MA: 1994
- 75 Yoneyama T, Crabtree RH. J. Mol. Catal. A: Chem. 1996; 108: 35
- 76 Emmert MH, Cook AK, Xie YJ, Sanford MS. Angew. Chem. Int. Ed. 2011; 50: 9409
- 77 Cook AK, Sanford MS. J. Am. Chem. Soc. 2015; 137: 3109
- 78 Cook AK, Emmert MH, Sanford MS. Org. Lett. 2013; 15: 5428
- 79 Gary JB, Cook AK, Sanford MS. ACS Catal. 2013; 3: 700
- 80 Tato F, García-Domínguez A, Cárdenas DJ. Organometallics 2013; 32: 7487
- 81 Desai SP, Mondal M, Choudhury J. Organometallics 2015; 34: 2731
- 82 Valderas C, Naksomboon K, Fernández-Ibáñez M. Á. ChemCatChem 2016; 8: 3213
- 83 Wu J, Hoang KL. M, Leow ML, Liu X.-W. Org. Chem. Front. 2015; 2: 502
- 84 Li L, Wang Y, Yang T, Zhang Q, Li D. Tetrahedron Lett. 2016; 57: 5859
- 85 Kim H, Chang S. ACS Catal. 2016; 6: 2341
- 86 Shrestha R, Mukherjee P, Tan Y, Litman ZC, Hartwig JF. J. Am. Chem. Soc. 2013; 135: 8480
- 87 Boursalian GB, Ngai M.-Y, Hojczyk KN, Ritter T. J. Am. Chem. Soc. 2013; 135: 13278
- 88 Zou L.-H, Reball J, Mottweiler J, Bolm C. Chem. Commun. 2012; 48: 11307
- 89 Cheng J.-H, Ramesh C, Kao H.-L, Wang Y.-J, Chan C.-C, Lee C.-F. J. Org. Chem. 2012; 77: 10369
- 90 Xu H.-J, Zhao Y.-Q, Feng T, Feng Y.-S. J. Org. Chem. 2012; 77: 2878
- 91 Liu Y, Kim J, Seo H, Park S, Chae J. Adv. Synth. Catal. 2015; 357: 2205
- 92a Iwasaki M, Iyanaga M, Tsuchiya Y, Nishimura Y, Li W, Li Z, Nishihara Y. Chem. Eur. J. 2014; 20: 2459
- 92b Iwasaki M, Nishihara Y. Dalton Trans. 2016; 45: 15278
- 93 Prasad CD, Balkrishna SJ, Kumar A, Bhakuni BS, Shrimali K, Biswas S, Kumar S. J. Org. Chem. 2013; 78: 1434
- 94 Yan S.-Y, Liu Y.-J, Liu B, Liu Y.-H, Shi B.-F. Chem. Commun. 2015; 51: 4069
- 95 Yan X.-B, Gao P, Yang H.-B, Li Y.-X, Liu X.-Y, Liang Y.-M. Tetrahedron 2014; 70: 8730
- 96 Shen C, Zhang P, Sun Q, Bai S, Hor TS. A, Liu X. Chem. Soc. Rev. 2015; 44: 291
- 97 Saravanan P, Anbarasan P. Org. Lett. 2014; 16: 848