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Synthesis 2014; 46(14): 1871-1880
DOI: 10.1055/s-0033-1338642
DOI: 10.1055/s-0033-1338642
special topic
Utilization of a Copper on Iron Catalyst for the Synthesis of Biaryl Systems and Benzoxazines via Oxidative Arylation of Anilide Derivatives
Further Information
Publication History
Received: 28 February 2014
Accepted after revision: 13 April 2014
Publication Date:
28 May 2014 (online)
Abstract
Heterogeneous copper on iron catalyst serves as an efficient alternative copper source for arylation reactions using hypervalent iodonium salts. The copper(0) catalyst affords meta-arylation of pivalanilides, while 2-ethynylanilides undergo oxidative carboarylation–ring closure with diaryliodonium salts.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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References
- 1a Hassan J, Sévignon M, Gozzi C, Schulz E, Lemaire M. Chem. Rev. 2002; 102: 1359
- 1b Alberico D, Scott ME, Lautens M. Chem. Rev. 2007; 107: 174
- 1c Stuart DR, Fagnou K. Science (Washington, D.C.) 2007; 316: 1172
- 1d Ackermann L, Vicente R, Kapdi AR. Angew. Chem. Int. Ed. 2009; 48: 9792
- 1e Bellina F, Rossi R. Tetrahedron 2009; 65: 10269
- 1f Joucla L, Djakovitch L. Adv. Synth. Catal. 2009; 351: 673
- 1g Chen X, Engle KM, Wang D.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
- 1h Satoh T, Miura M. Chem. Lett. 2007; 36: 200
- 1i Stuart DR, Villemure E, Fagnou K. J. Am. Chem. Soc. 2007; 129: 12072
- 1j Campeau L.-C, Schipper DJ, Fagnou K. J. Am. Chem. Soc. 2008; 130: 3266
- 1k Godula K, Sames D. Science (Washington, D.C.) 2006; 312: 67
- 1l Crabtree RH. J. Chem. Soc., Dalton Trans. 2001; 2437
- 1m Wencel-Delord J, Droge T, Liu F, Glorius F. Chem. Soc. Rev. 2011; 40: 4740
- 1n Mei T.-S, Kou L, Ma S, Engle KM, Yu J.-Q. Synthesis 2012; 44: 1778
- 1o Crabtree RH. Chem. Rev. 2010; 110: 575
- 1p Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
- 1q Neufeldt SR, Sanford MS. Acc. Chem. Res. 2012; 45: 936
- 2a Barder TE, Walker SD, Martinelli JR, Buchwald SL. J. Am. Chem. Soc. 2005; 127: 4685
- 2b Molander GA, Ellis N. Acc. Chem. Res. 2007; 40: 275
- 2c Zhang H, Cai Q, Ma D. J. Org. Chem. 2005; 70: 5164
- 2d Ley SV, Thomas AW. Angew. Chem. Int. Ed. 2003; 42: 5400
- 2e Mowery ME, DeShong P. J. Org. Chem. 1999; 64: 1684
- 2f Wentzel MT, Hewgley JB, Kamble RM, Wall PD, Kozlowski MC. Adv. Synth. Catal. 2009; 351: 931
- 2g Britcher LG, Kehoe DC, Matisons JG, Swincer AG. Macromolecules 1995; 28: 3110
- 3a Hypervalent Iodine Chemistry. In Topics in Current Chemistry. Wirth T. Springer; New York: 2003. 224 1-265
- 3b Bielawski M. Thesis. Stockholm University. Sweden,: 2008
- 3c Merritt EA, Olofsson B. Angew. Chem. Int. Ed. 2009; 48: 9052
- 3d Kalyani D, Deprez NR, Desai LV, Sanford MS. J. Am. Chem. Soc. 2005; 127: 7330
- 3e Parra A, Reboredo S. Chem. Eur. J. 2013; 19: 17244
- 3f Merritt EA, Malmgren J, Klinke FJ, Olofsson B. Synlett 2009; 2277
- 3g Bielawski M, Zhu M, Olofsson B. Adv. Synth. Catal. 2007; 349: 2610
- 4a Daugulis O, Zaitsev VG. Angew. Chem. Int. Ed. 2005; 44: 4046
- 4b Yang S, Li B, Wan X, Shi Z. J. Am. Chem. Soc. 2007; 129: 6066
- 4c Brasche G, García-Fortanet J, Buchwald SL. Org. Lett. 2008; 10: 2207
- 4d Wang G.-W, Yuan T.-T, Wu X.-L. J. Org. Chem. 2008; 73: 4717
- 4e Ciana C.-L, Phipps RJ, Brandt JR, Meyer F.-M, Gaunt MJ. Angew. Chem. Int. Ed. 2011; 50: 458
- 5a Zhang Y.-H, Shi B.-F, Yu J.-Q. J. Am. Chem. Soc. 2009; 131: 5072
- 5b Zhou Y, Zhao J, Liu L. Angew. Chem. Int. Ed. 2009; 48: 7126
- 5c Bedford RB, Mitchell CJ, Webster RL. Chem. Commun. 2010; 46: 3095
- 5d Cornella J, Righi M, Larrosa I. Angew. Chem. Int. Ed. 2011; 50: 9429
- 5e Akai S, Peat AJ, Buchwald SL. J. Am. Chem. Soc. 1998; 120: 9119
- 5f Do H.-Q, Khan RM. K, Daugulis O. J. Am. Chem. Soc. 2008; 130: 15185
- 5g Chen B, Hou X.-L, Li Y.-X, Wu Y.-D. J. Am. Chem. Soc. 2011; 133: 7668
- 6a Phipps RJ, Grimster NP, Gaunt MJ. J. Am. Chem. Soc. 2008; 130: 8172
- 6b Deprez NR, Kalyani D, Krause A, Sanford MS. J. Am. Chem. Soc. 2006; 128: 4972
- 7 Phipps RJ, Gaunt MJ. Science (Washington, D.C.) 2009; 323: 1593
- 8 Zhu S, MacMillan DW. C. J. Am. Chem. Soc. 2012; 134: 10815
- 9 Cahard E, Bremeyer N, Gaunt MJ. Angew. Chem. Int. Ed. 2013; 52: 9284
- 10 Sinai Á, Mészáros Á, Gáti T, Kudar V, Palló A, Novák Z. Org. Lett. 2013; 15: 5654
- 11a Tang B.-X, Song R.-J, Wu C.-Y, Liu Y, Zhou M.-B, Wei W.-T, Deng G.-B, Yin D.-L, Li J.-H. J. Am. Chem. Soc. 2010; 132: 8900
- 11b Duong HA, Gilligan RE, Cooke ML, Phipps RJ, Gaunt MJ. Angew. Chem. Int. Ed. 2011; 50: 463
- 11c Daugulis O, Do H.-Q, Shabashov D. Acc. Chem. Res. 2009; 42: 1074
- 11d Fujihara T, Xu T, Semba K, Terao J, Tsuji Y. Angew. Chem. Int. Ed. 2011; 50: 523
- 11e Phipps RJ, McMurray L, Ritter S, Duong HA, Gaunt MJ. J. Am. Chem. Soc. 2012; 134: 10773
- 11f Beletskaya IP, Cheprakov AV. Coord. Chem. Rev. 2004; 248: 2337
- 12 Lee EY, Park J. ChemCatChem 2011; 3: 1127
- 13 Kovács Sz, Zih-Perényi K, Révész Á, Novák Z. Synthesis 2012; 44: 3722
- 14a Kovács Sz, Novak Z. Org. Biomol. Chem. 2011; 9: 711
- 14b Kovács Sz, Novák Z. Tetrahedron 2013; 69: 8987
- 15 Bedford RB, Haddan MF, Webster RL, Mitchell CI. Angew. Chem. Int. Ed. 2011; 50: 5524
- 16 Sanford G. Science of Synthesis . Vol. 31. Ramsden CA. Georg Thieme Verlag; Stuttgart: 2007: 21