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DOI: 10.1055/s-0036-1589517
Transition-Metal-Catalyzed Reactions Involving Arynes
R.A.D thanks UGC-SRF research fellowship. S.B.M thanks great fully acknowledges generous financial support from DST-SERB, New Delhi.Publikationsverlauf
Received: 04. August 2017
Accepted after revision: 29. August 2017
Publikationsdatum:
22. November 2017 (online)

Abstract
The plethora of transformations attainable by the transition-metal-catalyzed reactions of arynes has found immense contemporary interest in the scientific community. This review highlights the scope and importance of transition-metal-catalyzed aryne reactions in the field of synthetic organic chemistry reported to date. It covers transformations achieved by the combination of arynes and various transition metals, which provide a facile access to a biaryl motif, fused polycyclic aromatic compounds, different novel carbocycles, various heterocycles, and complex natural products.
1 Introduction
2 Insertion of Arynes
3 Annulation of Arynes
4 Cycloaddition of Arynes
5 Multicomponent Reactions of Arynes
6 Miscellaneous Reactions of Arynes
7 Total Synthesis of Natural Products Using Arynes
8 Conclusion
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References
- 1 Pellissier H. Santelli M. Tetrahedron 2003; 59: 701
- 2 Wenk HH. Winkler M. Sander W. Angew. Chem. Int. Ed. 2003; 42: 502
- 3 Sanz R. Org. Prep. Proced. Int. 2008; 40: 215
- 4 Wentrup C. Aust. J. Chem. 2010; 63: 979
- 5 Tadross PM. Stoltz BM. Chem. Rev. 2012; 112: 3550
- 6 Gampe CM. Carreira EM. Angew. Chem. Int. Ed. 2012; 51: 3766
- 7 Bhunia A. Yetra SR. Biju AT. Chem. Soc. Rev. 2012; 41: 3140
- 8 Bhojgude SS. Biju AT. Angew. Chem. Int. Ed. 2012; 51: 1520
- 9 Yoshida H. Takaki K. Synlett 2012; 23: 1725
- 10 Yoshida H. Takaki K. Heterocycles 2012; 85: 1333
- 11a Pérez D. Peña D. Guitián E. Eur. J. Org. Chem. 2013; 5981
- 11b Dubrovskiy AV. Markina NA. Larock RC. Org. Biomol. Chem. 2013; 11: 191
- 12 Yoshida H. Aryne-Based Multicomponent Reactions. In Multicomponent Reactions in Organic Synthesis. Zhu J. Wang Q. Wang M.-X. Wiley-VCH; Weinheim: 2015: 39
- 13 Yoshida H. Nucleophilic Coupling with Arynes . In Comprehensive Organic Synthesis . 2nd ed., Vol. 4; Knochel P. Molander GA. Elsevier; Amsterdam: 2014: 517
- 14 Yoshida S. Hosoya T. Chem. Lett. 2015; 44: 1450
- 15a Bhojgude SS. Bhunia A. Biju AT. Acc. Chem. Soc. 2016; 49: 1658
- 15b García-López JA. Greaney MF. Chem. Soc. Rev. 2016; 45: 6766
- 15c Wu C. Shi F. Asian J. Org. Chem. 2013; 2: 116
- 15d Peña D. Pérez D. Guitián E. Heterocycles 2007; 74: 89
- 16 Stoermer R. Kahlert B. Ber. Dtsch. Chem. Ges. 1902; 35: 1633
- 17 Wittig G. Naturwissenschaften 1942; 30: 696
- 18 Roberts JD. Simmons HE. Carlsmith LA. Vaughan CW. J. Am. Chem. Soc. 1953; 75: 3290
- 19 Sapountzis I. Lin W. Fischer M. Knochel P. Angew. Chem. Int. Ed. 2004; 43: 4364
- 20 Dyke AM. Hester AJ. Lloyd-Jones GC. Synthesis 2006; 4093
- 21 Gilchrist TL. Science of Synthesis . Vol. 43. Hopf H. Thieme; Stuttgart: 2008: 151
- 22 Hoye TR. Baire B. Niu D. Willoughby PH. Woods BP. Nature (London) 2012; 490: 208
- 23 Antonio J. López G. Greaney MF. Org. Lett. 2014; 16: 2338
- 24 Ikawa T. Yamamoto R. Takagi A. Ito T. Shimizu K. Goto M. Hamashima Y. Akaia S. Adv. Synth. Catal. 2015; 357: 2287
- 25 Mesgar M. Daugulis O. Org. Lett. 2016; 18: 3910
- 26 Himeshima Y. Sonoda T. Kobayashi H. Chem. Lett. 1983; 1211
- 27 Worlikar SA. Larock RC. Curr. Org. Chem. 2011; 15: 3214
- 28a Yoshida H. Dearomatization–Aromatization Sequence. In Transition-Metal-Mediated Aromatic Ring Construction. Tanaka K. John Wiley; Hoboken: 2013: 773
- 28b Feng M. Jiang X. Synthesis 2017; 49: 4414
- 29 Akubathini S. Biehl E. Tetrahedron Lett. 2009; 50: 1809
- 30 Pawliczek M. Garve L. Werz D. Org. Lett. 2015; 17: 1716
- 31 Pareek M. Fallon T. Oestriech M. Org. Lett. 2015; 17: 2082
- 32 Pérez-Gómez M. García-López JA. Angew. Chem. Int. Ed. 2016; 55: 14389
- 33 Chen Q. Yan X. Du Z. Zhang K. Wen C. J. Org. Chem. 2016; 81: 9476
- 34 Yoon H. Lossouarn D. Landau F. Lautens M. Org. Lett. 2016; 18: 6324
- 35 Yao T. He D. Org. Lett. 2017; 19: 842
- 36 Lu C. Dubrovskiy AV. Larock RC. J. Org. Chem. 2012; 77: 8648
- 37 Huang X. Sha F. Tong J. Adv. Synth. Catal. 2010; 352: 379
- 38 Lu C. Markina NA. Larock RC. J. Org. Chem. 2012; 77: 11153
- 39 Dong Y. Liu B. Chen P. Liu Q. Wang M. Angew. Chem. Int. Ed. 2014; 53: 3442
- 40 Yuan W. Ma S. Org. Lett. 2014; 16: 193
- 41 Yang Y. Huang H. Wu L. Liang Y. Org. Biomol. Chem. 2014; 12: 5351
- 42 Tang CY. Wu XY. Sha F. Zhang F. Li H. Tetrahedron Lett. 2014; 55: 1036
- 43 Peng X. Wang W. Jiang C. Sun D. Xu Z. Tung C. Org. Lett. 2014; 16: 5354
- 44 Pimparkar S. Jeganmohan M. Chem. Commun. 2014; 50: 12116
- 45 Wang W. Peng X. Qin X. Zhao X. Ma C. Tung CH. Xu Z. J. Org. Chem. 2015; 80: 2835
- 46 Yao T. Zhang H. Zhao Y. Org. Lett. 2016; 18: 2532
- 47 Neog K. Borah A. Gogoi P. J. Org. Chem. 2016; 81: 11971
- 48 Zhang TY. Lin JB. Li QZ. Kang JC. Pan JL. Hou SH. Chen C. Zhang SY. Org. Lett. 2017; 19: 1764
- 49 Guitián E. Pérez D. Peña D. Top. Organomet. Chem. 2005; 14: 109
- 50 Hsieh JC. Cheng CH. Chem. Commun. 2005; 2459
- 51 Hsieh JC. Cheng CH. Chem. Commun. 2008; 2992
- 52 Saito N. Shiotani K. Kinbara A. Sato Y. Chem. Commun. 2009; 4284
- 53 Qiu Z. Xie Z. J. Am. Chem. Soc. 2009; 131: 2084
- 54 Qiu Z. Xie Z. Angew. Chem. Int. Ed. 2009; 48: 5729
- 55 Candito D. Lautens M. Synlett 2011; 1987
- 56 Lin Y. Wu L. Huang X. Eur. J. Org. Chem. 2011; 2993
- 57 Patel RM. Argade NP. Org. Lett. 2013; 15: 14
- 58 Parthasarathy K. Han H. Prakash C. Cheng CH. Chem. Commun. 2012; 48: 6580
- 59 Ni S. Shu W. Ma S. Synlett 2013; 24: 2310
- 60a Chen L. Zhang C. Wen C. Zhang K. Liu W. Chen Q. Catal. Commun. 2015; 65: 81
- 60b Schuler B. Collazos S. Gross L. Meyer G. Pérez D. Guitián E. Peña D. Angew. Chem. Int. Ed. 2014; 53: 9004
- 60c Lin JB. Shah TK. Goetz AE. Garg NK. Houk KN. J. Am. Chem. Soc. 2017; 139: 10447
- 61 Ganta A. Snowden TS. Org. Lett. 2008; 10: 5103
- 62 Berti F. Crotti P. Cassano G. Pineshi M. Synlett 2012; 23: 2463
- 63 Zeng Y. Zhang L. Zhao Y. Ni C. Zhao J. Hu J. J. Am. Chem. Soc. 2013; 135: 2955
- 64 Yoo W. Nguyen TN. Kobayashi S. Angew. Chem. Int. Ed. 2014; 53: 10213
- 65 Li J. Noyori S. Nakajima K. Nishihara Y. Organometallics 2014; 33: 3500
- 66 Yang J. Yu X. Wu J. Synthesis 2014; 46: 1362
- 67 Garve L. Werz D. Org. Lett. 2015; 17: 596
- 68 Feng M. Tang B. Wang N. Xu HX. Jiang X. Angew. Chem. Int. Ed. 2015; 54: 14960
- 69 Feng M. Tang B. Xu HX. Jiang X. Org. Lett. 2016; 18: 4352
- 70 Peng XL. Ma C. Tung CH. Xu Z. Org. Lett. 2016; 18: 4154
- 71 Zeng Y. Hu J. Org. Lett. 2016; 18: 856
- 72 García-López JA. Oliva-Madrid MJ. Saura-Llamas I. Bautista D. Vicente J. Chem. Commun. 2012; 48: 6744
- 73 Oliva-Madrid MJ. Saura-Llamas I. Bautista D. Vicente J. Chem. Commun. 2013; 49: 7997
- 74 Sibbel F. Daniliuc C. Studer A. Eur. J. Org. Chem. 2015; 4635
- 75 Mizukoshi Y. Mikami K. Uchiyama M. J. Am. Chem. Soc. 2015; 137: 74