RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2013; 45(2): 183-188
DOI: 10.1055/s-0032-1316824
DOI: 10.1055/s-0032-1316824
paper
Facile Preparation of Unsymmetrical Diaryl Ethers from Unsymmetrical Diaryliodonium Tosylates and Phenols with High Regioselectivity
Weitere Informationen
Publikationsverlauf
Received: 10. Oktober 2012
Accepted after revision: 13. November 2012
Publikationsdatum:
30. November 2012 (online)
Abstract
Unsymmetrical diaryl ethers were efficiently obtained in good yields by the reactions of aryl(4-methoxyphenyl)iodonium tosylates with phenols, and aryl(2,4-dimethoxyphenyl)iodonium tosylates with phenols, in the presence of potassium carbonate in acetonitrile, respectively. The latter iodonium tosylates provided the corresponding unsymmetrical diaryl ethers in good yields with high regioselectivities, together with the quantitative formation of 1-iodo-2,4-dimethoxybenzene.
-
References
- 1a Rao AV. R, Grujar MK, Reddy KL, Rao AS. Chem. Rev. 1995; 95: 2135
- 1b Zhu J. Synlett 1997; 133
- 1c Nicolaou KC, Boddy CN. C, Brase S, Winssinger N. Angew. Chem. Int. Ed. 1999; 38: 2096
- 1d Theil F. Angew. Chem. Int. Ed. 1999; 38: 2345
- 1e Sawyer JS. Tetrahedron 2000; 56: 5045
- 1f Evans DA, Katz JL, Peterson GS, Hintermann T. J. Am. Chem. Soc. 2001; 123: 12411
- 1g Nicolaou KC, Boddy CN. C. J. Am. Chem. Soc. 2002; 124: 10451
- 1h Crowley BM, Mori Y, McComas CC, Tang D, Boger DL. J. Am. Chem. Soc. 2004; 126: 4310
- 1i Frlan R, Kikelj D. Synthesis 2006; 2271
- 1j Pitsinos EN, Vidali VP, Couladouros EA. Eur. J. Org. Chem. 2011; 1207
- 1k Maligres PE, Li J, Krska SW, Schreier JD, Raheem IT. Angew. Chem. Int. Ed. 2012; 51: 9091
- 2a Ullmann F. Ber. Dtsch. Chem. Ges. 1901; 34: 2174
- 2b Ullmann F. Ber. Dtsch. Chem. Ges. 1903; 36: 2382
- 2c Ullmann F. Ber. Dtsch. Chem. Ges. 1904; 37: 853
- 2d Lindley J. Tetrahedron 1984; 40: 1433; and references cited therein
- 3a Finet JP, Fedorov AY, Combes S, Boyer G. Curr. Org. Chem. 2002; 6: 597
- 3b Ley SV, Thomas AW. Angew. Chem. Int. Ed. 2003; 42: 5400
- 3c Ma D, Cai Q. Org. Lett. 2003; 5: 3799
- 3d Evano G, Blanchard N, Toumi M. Chem. Rev. 2008; 108: 3054
- 3e Monnier F, Taillefer M. Angew. Chem. Int. Ed. 2008; 47: 3096
- 3f Monnier M, Taillefer M. Angew. Chem. Int. Ed. 2009; 48: 6954
- 3g Khalilzadeh MA, Hosseini A, Pilevar A. Eur. J. Org. Chem. 2011; 1587
- 3h Isomura Y, Narushima T, Kawasaki H, Yonezawa T, Obora Y. Chem. Commun. 2012; 48: 3784
- 3i Mulla SA. R, Inamdar SM, Pathan MY, Chavan SS. Tetrahedron Lett. 2012; 53: 1826
- 3j Verma S, Kumar N, Jain SL. Tetrahedron Lett. 2012; 53: 4665
- 3k Kuriyama M, Hamaguchi N, Onomura O. Chem.–Eur. J. 2012; 18: 1591
- 3l Chen J, Wang X, Zheng X, Ding J, Liu M, Wu H. Tetrahedron 2012; 68: 8905
- 4 Thomas AW. Diaryl Ethers . In Science of Synthesis . Vol. 31a, Section 31.6.1 Georg Thieme Verlag; Stuttgart: 2007: 469-543
- 5a Ishiyama T, Mori M, Suzuki A, Miyaura N. J. Organomet. Chem. 1996; 525: 225
- 5b Still IW. J, Toste FD. J. Org. Chem. 1996; 61: 7677
- 5c Hartwig JF. Angew. Chem. Int. Ed. 1998; 37: 2047
- 5d Aranyos A, Old DW, Kiyomori A, Wolfe JP, Sadighi JP, Buchwald SL. J. Am. Chem. Soc. 1999; 121: 4369
- 5e Mann G, Incarvito C, Rheingold AL, Hartwig JF. J. Am. Chem. Soc. 1999; 121: 3224
- 5f Muci AR, Buchwald SL. Top. Curr. Chem. 2002; 219: 131
- 5g Burgos CH, Barder TE, Huang XH, Buchwald SL. Angew. Chem. Int. Ed. 2006; 45: 4321
- 5h Hartwig JF. Nature (London, U. K.) 2008; 455: 314
- 5i Hu TJ, Schulz T, Torborg C, Chen XR, Wang J, Beller M, Huang J. Chem. Commun. 2009; 7330
- 5j Kim HJ, Kim M, Chang S. Org. Lett. 2011; 13: 2368
- 5k Salvi L, Davis NR, Ali SZ, Buchwald SL. Org. Lett. 2012; 14: 170
- 7a Varvoglis A. Hypervalent Iodine in Organic Synthesis . Academic Press; San Diego: 1996
- 7b Chun J, Pike VW. J. Org. Chem. 2012; 77: 1891
- 8a Crimmin MJ, Brown AG. Tetrahedron Lett. 1990; 31: 2017
- 8b Huang X, Zhu Q, Xu Y. Synth. Commun. 2001; 31: 2823
- 8c Liu H, Bernhardsen M, Fiksdahl A. Tetrahedron 2006; 62: 3564
- 8d Marsh G, Stenutz R, Bergman A. Eur. J. Org. Chem. 2003; 2566
- 9a Jalalian N, Ishikawa EE, Silva Jr LZ, Olofsson B. Org. Lett. 2011; 13: 1552
- 9b Jalalian N, Petersen TB, Olofsson B. Chem.–Eur. J. 2012; 18: 14140
- 10 Hossain MD, Kitamura T. Bull. Chem. Soc. Jpn. 2007; 80: 2213
- 11 Dohi T, Yamaoka N, Kita Y. Tetrahedron 2010; 66: 5775
- 12 Zhu M, Jalalian N, Olofsson B. Synlett 2008; 592
- 13 Dohi T, Ito M, Morimoto K, Minamitsuji Y, Takenaga N, Kita Y. Chem. Commun. 2007; 4152
- 14 Zhang M, Kumato K, Takei M, Fukumura T, Suzuki K. Appl. Radiat. Isot. 2007; 66: 1341
- 15 Haung RL. J. Chem. Soc. 1954; 3088
- 16 Weber FC, Sowa FJ. J. Am. Chem. Soc. 1938; 60: 94
- 17 Jammi S, Sakthivel S, Rout L, Mukherjee T, Mandal S, Mitra R, Saha P, Punniyamurthy T. J. Org. Chem. 2009; 74: 1971
- 18 Haung RL. J. Chem. Soc. 1954; 3088
- 19 Abramovitch RA, Alvernhe G, Bartnik R, Dassanayake NL, Inbasekaran MN, Kato S. J. Am. Chem. Soc. 1981; 103: 4558
- 20 Xu H, Chen Y. Synth. Commun. 2007; 37: 2411
- 21 Raiford LC, Colbert JC. J. Am. Chem. Soc. 1926; 48: 2652
- 22 Reilly J, Drumm PJ, Boyd Barret HS. J. Chem. Soc. 1927; 67
Recent reports: