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-00000083.xml
Synlett 2009(14): 2205-2216
DOI: 10.1055/s-0029-1217554
DOI: 10.1055/s-0029-1217554
ACCOUNT
© Georg Thieme Verlag
Stuttgart ˙ New YorkSynthesis of Fluorinated Arenes and Hetarenes Based on One-Pot Cyclizations of 1,3-Bis(trimethylsilyloxy)-1,3-butadienes
Further Information
Received
3 February 2009
Publication Date:
10 July 2009 (online)
Publication History
Publication Date:
10 July 2009 (online)
Abstract
One-pot cyclizations of fluorinated 1,3-bis(silyloxy)-1,3-butadienes and 3-alkoxy- and 3-silyloxy-2-en-1-ones provide a convenient access to various fluoro-, trifluoromethyl- and perfluoroalkyl-substituted arenes and hetarenes.
1 Introduction
2 [3+3]-Type Cyclizations of Fluorinated Enones
3 [3+3]-Type Cyclizations of Trifluoromethyl-Substituted Enones
4 [3+3]-Type Cyclizations of Perfluoroalkyl-Substituted Enones
5 [3+2]-Type Cyclizations of Fluorinated 1,3-Bis(silyloxy)-1,3-butadienes
6 [4+2]-Type Cyclizations of Fluorinated 1,3-Bis(silyloxy)-1,3-butadienes
7 Summary
Key words
arenes - heterocycles - cyclizations - organofluorine compounds - silyl enol ethers
- 1a
Fluorine in Bioorganic Chemistry
Filler R.Kobayasi Y.Yagupolskii LM. Elsevier; Amsterdam: 1993. - 1b
Filler R. Fluorine-Containing Drugs, In Organofluorine Chemicals and Their Industrial ApplicationBanks RE. Pergamon; New York: 1979. Chap. 6. - 1c
Hudlicky M. Chemistry of Organic Compounds Ellis Horwood; Chichester: 1992. - 1d
Kirsch P. Modern Fluoroorganic Chemistry VCH; Weinheim: 2004. - 1e
Chambers RD. Fluorine in Organic Chemistry Blackwell Publishing/CRC Press; Boca Raton: 2004. - 2a
Ryckmanns T.Balancon L.Berton O.Genicot C.Lamberty Y.Lallemand B.Passau P.Pirlot N.Quéré L.Talaga P. Bioorg. Med. Chem. Lett. 2002, 12: 261 - 2b
Malamas MS.Sredy J.Moxham C.Katz A.Xu W.McDevitt R.Adebayo FO.Sawicki DR.Seestaller L.Sullivan D.Taylor JR. J. Med. Chem. 2000, 43: 1293 - 2c
Ciha AJ.Ruminski PG. J. Agric. Food Chem. 1991, 39: 2072 - 3a
Albrecht HA.Beskid G.Georgopapadakou NH.Keith DD.Konzelmann FM.Pruess DL.Rossman PL.Wei CC.Christenson JG. J. Med. Chem. 1991, 34: 2857 - 3b
Albrecht HA.Beskid G.Christenson JG.Deitcher KH.Georgopapadakou NH.Keith DD.Konzelmann FM.Pruess DL.Wie CC. J. Med. Chem. 1994, 37: 400 - 3c
Song CW.Lee KY.Kim CD.Chang T.-M.Chey WY. J. Pharmacol. Exp. Ther. 1997, 281: 1312 - 3d
De Voss JJ.Sui Z.DeCamp DL.Salto R.Babe LM.Craik CS.Ortiz de Montellano PR.
J. Med. Chem. 1994, 37: 665 - 3e
Anjaiah S.Chandrasekhar S.Gree R. Adv. Synth. Catal. 2004, 346: 1329 - 3f
Iorio MA.Paszkowska RT.Frigeni V.
J. Med. Chem. 1987, 30: 1906 - 4a
Popp JL.Musza LL.Barrow CJ.Rudewicz PJ.Houck DR. J. Antibiot. 1994, 47: 411 - 4b
Chen TS.Petuch B.MacConnell J.White R.Dezeny G. J. Antibiot. 1994, 47: 1290 - 4c
Lam KS.Schroeder DR.Veitch JM.Colson KL.Matson JA.Rose WC.Doyle TW.Forenza S. J. Antibiot. 2001, 54: 1 - 5a
Schmidbaur H.Kumberger O. Chem. Ber. 1993, 126: 3 - 5b
Dinger MB.Henderson W. J. Organomet. Chem. 1998, 560: 233 - 5c
Liedtke J.Loss S.Widauer C.Grützmacher H. Tetrahedron 2000, 56: 143 - 5d
Schneider S.Tzschucke CC.Bannwarth W. In Multiphase Homogeneous CatalysisCornils B.Herrmann WA.Horvath IT.Leitner W.Mecking S.Olivier-Booubigou H.Vogt D. Wiley-VCH; Weinheim: 2005. Chap. 4. p.346 - 5e
Clarke D.Ali MA.Clifford AA.Parratt A.Rose P.Schwinn D.Bannwarth W.Rayner CM. Curr. Top. Med. Chem. 2004, 7: 729 - For reviews, see:
- 6a
Wittkopp A.Schreiner PR. The Chemistry of Dienes and Polyenes Vol. 2: Wiley & Sons; New York: 2000. - 6b
Schreiner PR. Chem. Soc. Rev. 2003, 32: 289 - See also:
- 6c
Wittkopp A.Schreiner PR. Chem. Eur. J. 2003, 9: 407 - 6d
Kleiner CM.Schreiner PR. Chem. Commun. 2006, 4315 - 6e
Kotke M.Schreiner PR. Synthesis 2007, 779 - 6f
Tsogoeva SB. Eur. J. Org. Chem. 2007, 1701 - 7 For a review of 1,3-bis(silyl enol
ethers) in general, see:
Langer P. Synthesis 2002, 441 - 8 For a review, see:
Langer P. Synlett 2006, 3369 - 9 For a review, see:
Feist H.Langer P. Synthesis 2007, 327 - 10 For a review, see:
Langer P. Synlett 2007, 1016 - 11 For a review, see:
Langer P. Eur. J. Org. Chem. 2007, 2233 - 12
Bellur E.Feist H.Langer P. Tetrahedron 2007, 63: 10865 - For reviews, see:
- 13a
Tredwell M.Gouverneur V. Org. Biomol. Chem. 2006, 4: 26 - 13b
Ma J.-A.Cahard D. Chem. Rev. 2004, 104: 6119 - 13c
Singh RP.Shreeve JM. Synthesis 2002, 2561 - 13d
Taylor SD.Kotoris CC.Hum G. Tetrahedron 1999, 55: 12431 - 13e
Purrington ST.Kagen BS.Patrick TB. Chem. Rev. 1986, 86: 997 - 13f
Nyffeler PT.Duron SG.Burkart MD.Vincent SP.Wong C.-H. Angew. Chem. Int. Ed. 2005, 44: 192 ; Angew. Chem. 2005, 117, 196 - 13g
Singh RP.Shreeve JM. Acc. Chem. Res. 2004, 37: 31 - 14
Banks RE.Besheesh MK.Mohialdin-Khaffaf SN.Sharif I. J. Chem. Soc., Perkin Trans. 1 1996, 2069 - 15
Stavber S.Jereb M.Zupan M. Synlett 1999, 1375 - 16 For a recent example of a Fries
rearrangement of 4-fluorophenol, see:
Sebille S.de Tullio P.Becker B.Antoine M.-H.Boverie S.Pirotte B.Lebrun P. J. Med. Chem. 2005, 48: 614 - 17a
Shi G.-q.Cottens S.Shiba SA.Schlosser MA. Tetrahedron 1992, 48: 10569 - 17b
Shi G.-q.Schlosser MA. Tetrahedron 1993, 49: 1445 - 17c
Patrick TB.Rogers J.Gorrell K. Org. Lett. 2002, 4: 3155 - 18
Lefebvre O.Brigaud T.Portella C. Tetrahedron 1998, 54: 5939 - 19a
Pundt T.Lau M.Hussain I.Yawer MA.Reinke H.Langer P. Tetrahedron Lett. 2007, 48: 2745 - 19b
Hussain I.Yawer MA.Lau M.Pundt T.Fischer C.Reinke H.Görls H.Langer P. Eur. J. Org. Chem. 2008, 503 - 20
Purrington ST.Bumgardner CL.Lazaridis NV.Singh P. J. Org. Chem. 1987, 52: 4307 - 21
Xu Z.-Q.DesMarteau DD.Gotoh Y. J. Chem. Soc., Chem. Commun. 1991, 179 - 22
Xiao J.-C.Shreeve JM. J. Fluorine Chem. 2005, 126: 475 ; and references cited therein - 23a
Chan T.-H.Brownbridge P. J. Am. Chem. Soc. 1980, 102: 3534 - 23b
Molander GA.Cameron KO. J. Am. Chem. Soc. 1993, 115: 830 - 24
Hussain I.Nguyen VTH.Yawer MA.Dang TT.Fischer C.Reinke H.Langer P. J. Org. Chem. 2007, 72: 6255 - 25a
Talapatra SK.Bose S.Mallik AK.Talapatra B. Tetrahedron 1985, 41: 2765 - 25b
Sargent MV. J. Chem. Soc., Perkin Trans. 1 1987, 2553 - 25c
Fan C.Wang W.Wang Y.Qin G.Zhao W. Phytochemistry 2001, 57: 1255 - 25d
Wu XY.Qin GW.Fan DJ.Xu RS. Phytochemistry 1994, 36: 477 - 26a
Namkung MJ.Fletcher TL. Can. J. Chem. 1967, 45: 2569 - 26b
Chambers RD.Spring DJ. Tetrahedron 1969, 25: 565 - 26c
Kyba EP.Liu S.-T.Chockalingam K.Reddy BR. J. Org. Chem. 1988, 53: 3513 - 27
Hamann LG.Winn DT.Pooley CLF.Tegley CM.West SJ.Farmer LJ.Zhi L.Edwards JP.Marschke KB.Mais DE.Goldman ME.Jones TK. Bioorg. Med. Chem. Lett. 1998, 8: 2731 - 28a
Reim S.Lau M.Langer P. Tetrahedron Lett. 2006, 47: 6903 - 28b
Reim S.Lau M.Adeel M.Hussain I.Yawer MA.Riahi A.Ahmed Z.Fischer C.Reinke H.Langer P. Synthesis 2009, 445 - 29 For a review, see:
McClinton MA.McClinton DA. Tetrahedron 1992, 48: 6555 - 30a
Paratian JM.Sibille S.Périchon J. J. Chem. Soc., Chem. Commun. 1992, 53 - 30b
Tordeux M.Langlois B.Wakselman C. J. Chem. Soc., Perkin Trans. 1 1990, 2293 - 31
Ding W.Pu J.Zhang C. Synthesis 1992, 635 - For cyclocondensations, see:
- 32a
Guan H.-P.Hu C.-M. Synthesis 1996, 1363 - 32b
Guan H.-P.Hu C.-M.
J. Fluorine Chem. 1996, 78: 101 - 32c
Guan H.-P.Hu Q.-S.Hu C.-M. Chin. J. Chem. 1996, 14: 87 - For the metalation of(trifluoromethyl)arenes and subsequent coupling with electrophiles, see:
- 33a
Marzi E.Mongin F.Spitaleri A.Schlosser M. Eur. J. Org. Chem. 2001, 2911 - 33b
Dmowski W.Piasecka-Maciejewska K. J. Fluorine Chem. 1996, 78: 59 - For Diels-Alder reactions, see:
- 34a
Abubakar AB.Booth BL.Suliman NNE.Tipping AE. J. Fluorine Chem. 1992, 56: 359 - 34b
Barlow MG.Suliman NNE.Tipping AE. J. Fluorine Chem. 1995, 70: 59 - 35a
Volochnyuk DM.Kostyuk AN.Sibgatulin DA.Chernega AN.Pinchuk AM.Tolmachev AA. Tetrahedron 2004, 60: 2361 - 35b
Volochnyuk DM.Kostyuk AN.Sibgatulin DA.Chernega AN. Tetrahedron 2005, 61: 2839 - 36a
Gambaryan NP.Simonyan LA.Petrovskii PV.
Izv. Akad. Nauk SSSR, Ser. Khim. 1967, 918 - 36b
Hojo M.Masuda R.Kokuryo Y.Shioda H.Matsuo S. Chem. Lett. 1976, 499 - 36c
Hojo M.Masuda R.Sakaguchi S.Takagawa M. Synthesis 1986, 1016 - 36d
Colla A.Martins MAP.Clar G.Krimmer S.Fischer P. Synthesis 1991, 483 - 36e
Hojo M.Masuda R.Okada E. Synthesis 1989, 215 - For reviews, see:
- 37a
Nenaidenko VG.Sanin AV.Balenkova ES. Russ. Chem. Rev. 1999, 68: 437 - 37b
Billard T. Chem. Eur. J. 2006, 12: 974 - 37c
Druzhinin SV.Balenkova ES.Nenajdenko VG. Tetrahedron 2007, 63: 7753 - 38
Zanatta N.Barichello R.Bonacorso HG.Martins MAP. Synthesis 1999, 765 - 39
Mamat C.Pundt T.Schmidt A.Langer P. Tetrahedron Lett. 2006, 47: 2183 - 40
Büttner S.Riahi A.Hussain I.Yawer MA.Lubbe M.Langer P. Tetrahedron 2009, 65: ??? - 41
Mamat C.Pundt T.Dang THT.Klassen R.Reinke H.Köckerling M.Langer P. Eur. J. Org. Chem. 2008, 492 - 42
Hussain I.Riahi A.Yawer MA.Görls H.Langer P. Org. Biomol. Chem. 2008, 6: 3542 - 43a
Moriguchi T.Endo T. J. Org. Chem. 1995, 60: 3523 - 43b
Trost BM.Balkovec JM.Mao MKT. J. Am. Chem. Soc. 1983, 105: 6755 - 43c
Effenberger F.Maier R.Schönwälder K.-H.Ziegler T. Chem. Ber. 1982, 115: 2766 - 44
Bonacorso HG.Costa MB.Moura S.Pizzuti L.Martins MAP.Zanatta N.Flores AFC. J. Fluorine Chem. 2005, 126: 1396 - 45
Flores AFC.Siqueira GM.Freitag R.Zanatta N.Martins MAP. Quim. Nova 1994, 17: 298 - 46
Schmidt U.Grafen P. Justus Liebigs Ann. Chem. 1962, 656: 97 - 47
Kamigata N.Udodaira K.Shimizu T. J. Chem. Soc., Perkin Trans. 1 1997, 783 - 48
Piatnitski EL.Duncton MAJ.Kiselyov AS.Katoch-Rouse R.Sherman D.Milligan DL.Balagtas C.Wong WC.Kawakami J.Doody JF. Bioorg. Med. Chem. Lett. 2005, 15: 4696 - 49
Yoshida M.Morinaga Y.Iyoda M. J. Fluorine Chem. 1994, 68: 33 - 50a
Olah GA.Comisarow MB. J. Am. Chem. Soc. 1969, 91: 2955 - 50b
Sheppard WA. Tetrahedron 1971, 27: 945 - 50c
He J.Pittman CU. Synth. Commun. 1999, 29: 855 - 51
Rozen S.Mishani E. J. Chem. Soc., Chem. Commun. 1994, 2081 - 52a
Saint-Jalmes L. J. Fluorine Chem. 2006, 127: 85 - 52b
Anguille S.Garayt M.Schanen V.Gree R. Adv. Synth. Catal. 2006, 348: 1149 - 53
Jones RG. J. Am. Chem. Soc. 1947, 69: 2350 - 54a
Fuqua SA.Parkhurst RM.Silverstein RM. Tetrahedron 1964, 20: 1625 - 54b
Haas A.Spitzer M.Lieb M. Chem. Ber. 1988, 121: 1329 - 55a
Dolbier WR.Asghar MA.Pan H.-Q.Celewicz L. J. Org. Chem. 1993, 58: 1827 - 55b
He J.Pittman CU. Synth. Commun. 1999, 29: 855 - 56
Lubbe M.Mamat C.Langer P. Synlett 2008, 1684 - 57
Dolbier WR.Médebielle M.Ait-Mohand S. Tetrahedron Lett. 2001, 42: 4811 - 58 The reaction was carried out following
the procedure reported for the synthesis of 4,4-diethoxy-1,1,1-trifluoro-but-3-en-2-one;
see:
Hojo M.Masuda R.Okada E. Synthesis 1986, 1013 - 59a
Liquid Crystals
Stegemeyer H. Steinkopff/Springer; New York: 1994. - 59b
Miethchen R.Hein M. Carbohydr. Res. 2000, 327: 169 - 59c
Hein M.Miethchen R.Schwäbisch D.Schick C. Liq. Cryst. 2000, 27: 163 - 59d
Schwäbisch D.Wille S.Hein M.Miethchen R. Liq. Cryst. 2004, 31: 1143 - 59e
Nicoletti M.Bremer M.Kirsch P.O’Hagan D. Chem. Commun. 2007, 5075 - 59f
Kirsch P.Hahn A.Fröhlich R.Haufe G. Eur. J. Org. Chem. 2006, 4819 ; and references cited therein - 60
Burton DJ.Yang Z. Tetrahedron 1992, 48: 189 - 61
Chanteau F.Plantier-Royon R.Haufe G.Portella C. Tetrahedron 2006, 62: 9049 - 62 For a review, see:
Portella C.Muzard M.Bouillon J.-P.Brulé C.Grellepois F.Shermolovich YG.Timoshenko VM.Chernega AN.Sotoca-Usina E.Gil S. Heteroat. Chem. 2007, 18: 500 - 63
Bouillon J.-P.Kikelj V.Tinant B.Harakat D.Portella C. Synthesis 2006, 1050 - 64
Sootoca E.Bouillon J.-P.Gil S.Parra M.Portella C. Tetrahedron 2005, 61: 4395 - 65
Tolmachova NA.Gerus II.Vdovenko SI.Haufe G.Kirzhner YA. Synthesis 2007, 3797 - 66
Leuger J.Blond G.Fröhlich R.Billard T.Haufe G.Langlois BR. J. Org. Chem. 2006, 71: 2735 - 67
Büttner S.Lubbe M.Reinke H.Fischer C.Langer P. Tetrahedron 2008, 64: 7968 - 68a
Moore RA.Levine R. J. Org. Chem. 1964, 29: 1439 - 68b
Ishihara T.Seki T.Ando T. Bull. Chem. Soc. Jpn. 1982, 55: 3345 - 68c
Park JD.Brown HA.Lacher JR. J. Am. Chem. Soc. 1953, 75: 4753 - 68d
Kurykin MA.Vol’pin IM.German LS. J. Fluorine Chem. 1996, 80: 9 - 68e
Nikolaev VA.Kantin GP.Utkin PY. Russ. J. Org. Chem. 1994, 30: 1354 - 68f
Trabelsi H.Cambon A. Synthesis 1992, 315 - 68g
Massyn C.Pastor R.Cambon A. Bull. Soc. Chim. Fr. 1974, 975 - 69
Lubbe M.Mamat C.Fischer C.Langer P. Tetrahedron 2007, 63: 413 - 70
Husted DR.Ahlbrecht AH. J. Am. Chem. Soc. 1953, 75: 1605 - 71
Malik AA.Sharts CM. J. Fluorine Chem. 1987, 34: 395 - 72
Adeel M.Reim S.Wolf V.Yawer MA.Hussain I.Villinger A.Langer P. Synlett 2008, 2629 - 73
Langer P.Stoll M.Schneider S. Chem. Eur. J. 2000, 6: 3204 - 74
Langer P.Armbrust H.Eckardt T.Magull J. Chem. Eur. J. 2002, 8: 1443 - 75a
Bellur E.Görls H.Langer P. Eur. J. Org. Chem. 2005, 2074 - See also:
- 75b
Langer P.Krummel T. Chem. Eur. J. 2001, 7: 1720 - 76a
Langer P.Appel B. Tetrahedron Lett. 2003, 44: 5133 - 76b
Rashid MA.Rasool N.Appel B.Adeel M.Karapetyan V.Mkrtchyan S.Reinke H.Fischer C.Langer P. Tetrahedron 2008, 64: 5416 - 77a
Langer P.Kracke B. Tetrahedron Lett. 2000, 41: 4545 - 77b
Hussain I.Yawer MA.Appel B.Sher M.Mahal A.Villinger A.Fischer C.Langer P. Tetrahedron 2008, 64: 8003 - 79a
Emmrich T.Reinke H.Langer P. Synthesis 2006, 2551 - 79b
Hussain I.Yawer MA.Lalk M.Lindequist M.Villinger A.Fischer C.Langer P. Bioorg. Med. Chem. 2008, 16: 9898
References
Farooq, I.; Langer, P. unpublished results.