Potassium tert-Butoxide Mediated O-Arylation of N-Hydroxyphthalimide and Oximes with Diaryliodonium Salts

Luis C. Misal Castro; Naoto Chatani

doi:10.1055/s-0033-1340192

Synthesis, Table of Contents

Synthesis 2014; 46(17): 2312-2316
DOI: 10.1055/s-0033-1340192

paper

Potassium tert-Butoxide Mediated O-Arylation of N-Hydroxyphthalimide and Oximes with Diaryliodonium Salts

Authors

Luis C. Misal Castro

Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan Fax: +81(6)68797396 Email: chatani@chem.eng.osaka-u.ac.jp
Naoto Chatani*

Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan Fax: +81(6)68797396 Email: chatani@chem.eng.osaka-u.ac.jp

Abstract

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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.

Key words

O-arylation - O-arylhydroxylamines - oximes - N-hydroxyphthalimide - diaryliodonium salts

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References

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

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