Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2006(14): 2271-2285
DOI: 10.1055/s-2006-942440
DOI: 10.1055/s-2006-942440
REVIEW
© Georg Thieme Verlag Stuttgart · New York
Recent Progress in Diaryl Ether Synthesis
Further Information
Received
6 December 2005
Publication Date:
29 June 2006 (online)
Publication History
Publication Date:
29 June 2006 (online)
Abstract
Diaryl ethers form an important class of organic compounds, both in life sciences and in the polymer industry. In general, diaryl ethers can be synthesized by means of copper-catalyzed Ullmann diaryl ether coupling, palladium-catalysed Buchwald-Hartwig reaction, nucleophilic aromatic substitution, arylboronic acid diaryl ether coupling, oxidative coupling, and nucleophilic aromatic addition to metal-arene complexes. This review covers the progress in diaryl ether synthesis since 1999, with literature coverage through September 2005.
-
1 Introduction
-
2 Ullmann and Buchwald-Hartwig Diaryl Ether Coupling Reactions
-
2.1 Intermolecular Ullmann Diaryl Ether Coupling Reactions
-
2.2 Intermolecular Palladium-Catalyzed Diaryl Ether Coupling Reactions
-
2.3 Intramolecular Palladium- and Copper-Mediated Diaryl Ether Coupling Reactions
-
3 Synthesis of Diaryl Ethers via Nucleophilic Aromatic Substitution
-
3.1 Intermolecular Nucleophilic Aromatic Substitution
-
3.2 Intramolecular Nucleophilic Aromatic Substitution
-
4 Coupling of Phenols with Arylboronic Acids
-
4.1 Intermolecular Coupling of Phenols with Arylboronic Acids
-
4.2 Intramolecular Coupling of Phenols with Arylboronic Acids
-
5 Diaryl Ether Synthesis via Benzyne Mechanism
-
6 SnAr Additions to Metal-Arene Complexes
-
6.1 Intermolecular SnAr Additions to Metal-Arene Complexes
-
6.2 Intramolecular SnAr Additions to Metal-Arene Complexes
-
7 Diaryl Ether Synthesis via Oxidative Coupling
-
8 Diaryl Ether Synthesis by Fischer Chromium Carbene Mediated Benzannulation
-
9 Summary
Key words
diaryl ether - Ullmann reaction - coupling reactions - Buchwald-Hartwig reaction - arylboronic acids
- 1
Theil F. Angew. Chem. Int. Ed. 1999, 38: 2345 -
2a
Zhu J. Synlett 1997, 133 -
2b
Boger DL.Patane MA.Zhou J. J. Am. Chem. Soc. 1994, 116: 8544 - 3
Kase H.Kaneko M.Yamado K. J. Antibiot. 1987, 40: 450 -
4a
Tamai S.Kaneda M.Nakamura S. J. Antibiot. 1982, 35: 1130 -
4b
Kaneda M.Tamai S.Nakamura S.Hirata T.Kushi Y.Suga T. J. Antibiot. 1982, 35: 1137 -
5a
Kazlauskus R.Lidgard RO.Murphy PT.Wells RJ.Blount JF. Aust. J. Chem. 1981, 34: 765 -
5b
Franklin MA.Penn SG.Lebrilla CB.Lam TH.Pessah IN.Molinski TF. J. Nat. Prod. 1996, 59: 1121 - 6
Fotsch C.Sonnenberg DJ.Chen N.Hale C.Karbon W.Norman MH. J. Med. Chem. 2001, 44: 2344 - 7
The Pesticide Manual
10th ed.:
Tomlin C. Crop Protection Publications; Farnham UK: 1994. -
8a
Ullman F. Chem. Ber. 1904, 37: 853 -
8b
Ullman F. Chem. Ber. 1901, 34: 2174 -
8c
Ullman F. Chem. Ber. 1903, 36: 2382 -
8d
Ullman F.Sponagel P. Chem. Ber. 1905, 36: 2211 - 9
Goldberg I. Chem. Ber. 1906, 39: 1691 - 10
Lindley J. Tetrahedron 1984, 40: 1433 - 11
Goodbrand HB.Hu NK. J. Org. Chem. 1999, 64: 670 - 12
Fagan PJ.Hauptman E.Shapiro R.Casalnuovo A. J. Am. Chem. Soc. 2000, 122: 5043 - 13
Sawyer JS. Tetrahedron 2000, 56: 5045 - 14
Finet JP.Fedorov AY.Combes S.Boyer G. Curr. Org. Chem. 2002, 6: 597 - 15
Beletskaya IP.Cheprakov AV. Coord. Chem. Rev. 2004, 248: 2337 - 16
Kunz K.Scholz U.Ganzer D. Synlett 2003, 2428 - 17
Ley S.Thomas AW. Angew. Chem. Int. Ed. 2003, 42: 5400 - 18
Wipf P.Jung JK. J. Org. Chem. 2000, 65: 6319 - 19
Xing X.Padmanaban D.Yeh LA.Cuny GD. Tetrahedron 2002, 58: 7903 - 20
Paine AJ. J. Am. Chem. Soc. 1987, 109: 1496 - 21
Saphier M.Burg A.Sheps S.Cohen H.Meyerstein D. J. Chem. Soc. Dalton Trans. 1999, 1845 - 22
Buck E.Song JZ.Tschaen D.Dormer PG.Volante RP.Reider PJ. Org. Lett. 2002, 4: 1623 -
23a
Ma D.Cai Q.Zhang H. Org. Lett. 2003, 5: 2453 -
23b
Ma D.Cai Q. Org. Lett. 2003, 5: 3799 - 24
Hosseinzadeh R.Tajbakhsh M.Mohadjerani M.Alikarami M. Synlett 2005, 1101 - 25
Cristau H.-J.Cellier PP.Hamada S.Spindler J.-F.Taillefer M. Org. Lett. 2004, 6: 913 - 26
Kalinin AV.Bower JF.Riebel P.Snieckus V. J. Org. Chem. 1999, 64: 2986 - 27
Marcoux J.-F.Doye S.Buchwald SL. J. Am. Chem. Soc. 1997, 119: 10539 - 28
Gujadhur R.Venkataraman D. Synth. Commun. 2001, 31: 2865 - 29
Gujadhur RK.Bates GC.Venkataraman D. Org. Lett. 2001, 3: 4315 - 30
Xu LW.Xia CG.Li JW.Hu XX. Synlett 2003, 2071 -
31a
Pellón RF.Docampo ML. Synth. Commun. 2003, 33: 921 -
31b
Pellón RF.Docampo M.Jáuregui U. Rev. CNIC Cienc. Quim. 1999, 30: 55 - 32
Lee AJ.Sowell JW.Cotham WE.Zhu BT. Steroids 2004, 69: 61 - 33
Lawrence NJ.Rennison D.Woo M.McGown AT.Hadfiel JA. Bioorg. Med. Chem. Lett. 2001, 11: 51 - 34
Luo Y.Wu JX.Ren RX. Synlett 2003, 1734 - 35
Chauhan SMS.Jain N.Kumar A.Srinivas KA. Synth. Commun. 2003, 33: 3607 - 36
Knepper K.Lormann MEP.Bräse S. J. Comb. Chem. 2004, 6: 460 - 37
Palucki M.Wolfe JP.Buchwald SL. J. Am. Chem. Soc. 1996, 118: 10333 - 38
Mann G.Hartwig JF. J. Am. Chem. Soc. 1996, 118: 13109 - 39
Mann G.Incarvito C.Rheingold AL.Hartwig JF. J. Am. Chem. Soc. 1999, 121: 3224 - 40
Aranyos A.Old DW.Kiyomori A.Wolfe JP.Sadighi JP.Buchwald SL. J. Am. Chem. Soc. 1999, 121: 4369 - 41
Shelby Q.Kataoka N.Mann G.Hartwig J. J. Am. Chem. Soc. 2000, 122: 10718 - 42
Kataoka N.Shelby Q.Stambuli JP.Hartwig JF. J. Org. Chem. 2002, 67: 5553 - 43
Harkal S.Kumar K.Michalik D.Zapf A.Jackstell R.Rataboul F.Riermeier T.Monsees A.Beller M. Tetrahedron Lett. 2005, 46: 3237 -
44a
Olivera R.SanMartin R.Churruca F.Domínguez E. J. Org. Chem. 2002, 67: 7215 -
44b
Olivera R.SanMartin R.Domínguez E. Tetrahedron Lett. 2000, 41: 4357 - 45
De la Fuente JA.Manzanaro S.Martin MJ.Queseda TG.Reymundo I.Luengo MS.Gago F. J. Med. Chem. 2003, 46: 5208 -
46a
Nicolaou KC.Boddy CNC. J. Am. Chem. Soc. 2002, 124: 10451 -
46b
Nicolaou KC.Boddy CNC.Natarajan S.Yue TY.Li H.Brase S.Ramanjulu JM. J. Am. Chem. Soc. 1997, 119: 3421 - 47
Wang J.-Q.Harvey RG. Tetrahedron 2002, 58: 5927 - 48
Bigot A.Bois-Choussy M.Zhu J. Tetrahedron Lett. 2000, 41: 4573 - 49
Li F.Wang Q.Ding Z.Tao F. Org. Lett. 2003, 5: 2169 - 50
Li F.Meng Q.Chen H.Li Z.Wang Q.Tao F. Synthesis 2005, 1305 - 51
Chaouchi M.Loupy A.Marque S.Petit A. Eur. J. Org. Chem. 2002, 1278 - 52
Cui S.-L.Jiang Z.-Y.Wang Y.-G. Synlett 2004, 1829 - 53
Urgaonkar S.Verkade JG. Org. Lett. 2005, 7: 3319 - 54
Zhao JK.Wang YG. Chinese Chem. Lett. 2003, 14: 1012 - 55
Bois-Choussy M.Vergne C.Neuville L.Beugelmans R.Zhu J. Tetrahedron Lett. 1997, 38: 5759 - 56
Neuville L.Bois-Choussy M.Zhu J. Tetrahedron Lett. 2000, 41: 1747 - 57
Cristau P.Vors J.-P.Zhu J. Tetrahedron Lett. 2003, 44: 5575 - 58
Boisnard S.Zhu J. Tetrahedron Lett. 2002, 43: 2577 - 59
Cristau P.Vors J.-P.Zhu J. Tetrahedron 2003, 59: 7859 - 60
Ma N.Jia Y.Liu Z.Gonzales-Zamora E.Bois-Choussy M.Malabarba A.Brunati C.Zhu J. Bioorg. Med. Chem. Lett. 2005, 15: 743 - 61
Bois-Choussy M.Cristau P.Zhu J. Angew. Chem. Int. Ed. 2003, 42: 4238 - 62
Ouyang X.Chen Z.Liu L.Dominguez C.Kiselyov AS. Tetrahedron 2000, 56: 2369 - 63
Chan DMT.Monaco KL.Wang R.Winters MP. Tetrahedron Lett. 1998, 39: 2933 - 64
Evans DA.Katz JL.West TR. Tetrahedron Lett. 1998, 39: 2937 - 65
Chan DMT.Monaco KL.Li R.Bonne D.Clark CG.Lam PYS. Tetrahedron Lett. 2003, 44: 3863 - 66
Jung ME.Lazarova TI. J. Org. Chem. 1999, 64: 2976 - 67
Simon J.Salzbrunn S.Prakash GKS.Petasis NA.Olah GA. J. Org. Chem. 2001, 66: 633 - 68
Sagar AD.Tale RH.Adude RN. Tetrahedron Lett. 2003, 44: 7061 - 69
Lam PYS.Vincent G.Clark CG.Deudon S.Jadhav PK. Tetrahedron Lett. 2001, 42: 3415 - 70
Evans DA.Katz JL.Peterson GS.Hintermann T. J. Am. Chem. Soc. 2001, 123: 12411 - 71
Quach TD.Batey RA. Org. Lett. 2003, 5: 1381 - 72
Vedejs E.Fields SC.Schrimpf MR. J. Am. Chem. Soc. 1993, 115: 11612 - 73
Chiang GCH.Olsson T. Org. Lett. 2004, 6: 3079 - 74
Decicco CP.Song Y.Evans DA. Org. Lett. 2001, 3: 1029 - 75
Hitotsuyanagi Y.Ishikawa H.Naito S.Takeya K. Tetrahedron Lett. 2003, 44: 5901 - 76
Liu Z.Larock RC. Org. Lett. 2004, 6: 99-102 - 77
Pearson AJ.Belmont PO. Tetrahedron Lett. 2000, 41: 1671 - 78
Leone-Stumpf D.Lindel T. Eur. J. Org. Chem. 2003, 1853 - 79
Schmid A.Lindel T. Angew. Chem. Int. Ed. 2004, 43: 1581 - 80
Venkatraman S.Njoroge FG.Girijavallabhan V. Tetrahedron 2002, 58: 5453 - 81
Evans DA.Dinsmore CJ.Ratz AM. Tetrahedron Lett. 1997, 38: 3189 - 82
Ito M.Yamanaka M.Kutsumura N.Nishiyama S. Tetrahedron 2004, 60: 5623 - 83
Kotoku N.Tsujita H.Hiramatsu A.Mori C.Koizumi N.Kobayashi M. Tetrahedron 2005, 61: 7211 - 84
Nakamura K.Nishiya H.Nishiyama S. Tetrahedron Lett. 2001, 42: 6311 - 85
Saitoh T.Ichikawa J. J. Am. Chem. Soc. 2005, 127: 9696 - 86
Tanabe T.Doi F.Ogamino T.Nishiyama S. Tetrahedron Lett. 2004, 45: 3477 - 87
Pulley SR.Sen S.Vorogushin A.Swanson E. Org. Lett. 1999, 1: 1721 - 88
Dötz KH. Angew. Chem., Int. Ed. Engl. 1975, 14: 644