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Synthesis 2014; 46(17): 2312-2316
DOI: 10.1055/s-0033-1340192
DOI: 10.1055/s-0033-1340192
paper
Potassium tert-Butoxide Mediated O-Arylation of N-Hydroxyphthalimide and Oximes with Diaryliodonium Salts
Further Information
Publication History
Received: 31 March 2014
Accepted after revision: 30 April 2014
Publication Date:
12 June 2014 (online)
Abstract
A metal-free method for the direct O-arylation of N-hydroxyphthalimide, pyridine-2-carboxaldehyde oxime, acetophenone oxime, or dimethylglyoxime with diaryliodonium salts under mild reaction conditions and short reaction time in the presence of potassium tert-butoxide is reported. The diaryliodonium counterion salt plays an important role in the reaction when it is carried out at 40 °C or lower temperatures.
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 Takeda N, Miyata O, Naito T. Eur. J. Org. Chem. 2007; 1491
- 1b Contiero F, Jones KM, Matts EA, Porzelle A, Tomkinson NC. O. Synlett 2009; 3003
- 2a Guru MM, Ali MA, Punniyamurthy T. Org. Lett. 2011; 13: 1194
- 2b Guru MM, Ali MA, Punniyamurthy T. J. Org. Chem. 2011; 76: 5295
- 3a Johnson SM, Petrassi HM, Palaninathan SK, Mohamedmohaideen NN, Purkey HE, Nichols C, Chiang KP, Walkup T, Sacchettini JC, Sharpless KB, Kelly JW. J. Med. Chem. 2005; 48: 1576
- 3b Ali A, Altamore TM, Bliese M, Fisara P, Liepa AJ, Meyer AG, Nguyen O, Sargent RM, Sawutz DG, Winkler DA, Winzenberg KN, Ziebell A. Bioorg. Med. Chem. Lett. 2008; 18: 252
- 3c Tang D, Gai Y, Polemeropoulos A, Chen Z, Wang Z, Or YS. Bioorg. Med. Chem. Lett. 2008; 18: 5078
- 4 Legault C, Charette AB. J. Org. Chem. 2003; 68: 7119
- 5 Baumann JB. Synthesis 1975; 782
- 6 Baldoli C, Del Buttero P, Licandro E, Maiorana S. Synthesis 1988; 344
- 7 Petrassi HM, Sharpless KB, Kelly JW. Org. Lett. 2001; 3: 139
- 8 Ali A, Meyer AG, Tuck KL. Synlett 2009; 955
- 9 Feng X.-H, Zhang G.-Z, Chen C.-Q, Yang M.-Y, Xu X.-Y, Huang G.-S. Synth. Commun. 2009; 39: 1768
- 10 Wang L, Huang C, Cai C. Catal. Commun. 2010; 11: 532
- 11 Mondal M, Sarmah G, Gogoi K, Bora U. Tetrahedron Lett. 2012; 53: 6219
- 12 De P, Nonappa Pandurangan K, Maitra U, Wailes S. Org. Lett. 2007; 9: 2767
- 13 Maimone TJ, Buchwald SL. J. Am. Chem. Soc. 2010; 132: 9990
- 14a Liu G, Shen Y, Zhou Z, Lu X. Angew. Chem. Int. Ed. 2013; 52: 6033
- 14b Shen Y, Liu G, Zhou Z, Lu X. Org. Lett. 2013; 15: 3366
- 14c Duan P, Yang Y, Ben R, Yan Y, Dai L, Hong M, Wu Y.-D, Wang D, Zhang X, Zhao J. Chem. Sci. 2014; 5: 1574
- 14d Hu F, Xia Y, Ye F, Liu Z, Ma C, Zhang Y, Wang J. Angew. Chem. Int. Ed. 2014; 53: 1364 ; Angew. Chem. 2014, 126, 1388
-
15a Merritt EA, Olofsson B. Angew. Chem. Int. Ed. 2009; 48: 9052
- 15b Silva JL. F, Olofsson B. Nat. Prod. Rep. 2011; 28: 1722
- 16a Bielawski M, Zhu M, Olofsson B. Adv. Synth. Catal. 2007; 349: 2610
- 16b Bielawski M, Olofsson B. Chem. Commun. 2007; 2521
- 16c Bielawski M, Aili D, Olofsson B. J. Org. Chem. 2008; 73: 4602
- 17a Jalalian N, Ishikawa EE, Silva LF, Olofsson B. Org. Lett. 2011; 13: 1552
- 17b Petersen TB, Khan R, Olofsson B. Org. Lett. 2011; 13: 3462
-
17c Ackermann L, Dell’Acqua M, Fenner S, Vicente R, Sandmann R. Org. Lett. 2011; 13: 2358
-
17d Wen J, Zhang R.-Y, Chen S.-Y, Zhang J, Yu X.-Q. J. Org. Chem. 2012; 77: 766
- 17e Li J, Liu L. RSC Adv. 2012; 2: 10485
- 17f Jalalian N, Petersen TB, Olofsson B. Chem. Eur. J. 2012; 18: 14140
- 17g Guo F, Wang L, Wang P, Yu J, Han J. Asian J. Org. Chem. 2012; 1: 218
-
17h Castro S, Fernandez JJ, Vicente R, Fananas FJ, Rodriguez F. Chem. Commun. 2012; 48: 9089
- 17i Lindstedt E, Ghosh R, Olofsson B. Org. Lett. 2013; 15: 6070
- 17j Kakinuma Y, Moriyama K, Togo H. Synthesis 2013; 45: 183
- 17k Umierski N, Manolikakes G. Org. Lett. 2013; 15: 4972
- 17l Tobisu M, Furukawa T, Chatani N. Chem. Lett. 2013; 42: 1203
- 17m Yamaoka N, Sumida K, Itani I, Kubo H, Ohnishi Y, Sekiguchi S, Dohi T, Kita Y. Chem. Eur. J. 2013; 19: 15004
- 17n Malmgren J, Santoro S, Jalalian N, Himo F, Olofsson B. Chem. Eur. J. 2013; 19: 10334
-
17o Xu Q.-L, Gao H, Yousufuddin M, Ess DH, Kürti L. J. Am. Chem. Soc. 2013; 135: 14048
- 17p Wagner AM, Sanford MS. J. Org. Chem. 2014; 79: 2263
- 18 Cadogan JI. G, Rowley AG. Synth. Commun. 1977; 7: 365
- 19 Ghosh R, Olofsson B. Org. Lett. 2014; 16: 1830
- 20 Storr TE, Greaney MF. Org. Lett. 2013; 15: 1410
- 21 Wagner AM, Sanford MS. Org. Lett. 2011; 13: 28