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(23): 3963-3966
DOI: 10.1055/s-2006-950326
DOI: 10.1055/s-2006-950326
PAPER
© Georg Thieme Verlag Stuttgart · New York
Bismuth Triflate Catalyzed [1,3] Rearrangement of Aryl 3-Methylbut-2-enyl Ethers
Further Information
Received
18 July 2006
Publication Date:
20 October 2006 (online)
Publication History
Publication Date:
20 October 2006 (online)

Abstract
An efficient bismuth triflate catalyzed [1,3] rearrangement of aryl 3-methylbut-2-enyl ethers has been developed. The reaction proceeds rapidly and affords the corresponding para- and ortho-prenylated phenols and naphthols in moderate to good yields (up to 86%). ortho-Prenylphenols are immediately cyclized under the reaction conditions to the corresponding chroman derivatives.
Key words
bismuth - bismuth triflate - [1,3] rearrangement - Lewis acid - allyl phenyl ethers
- 1
Narayan S.Muldoon J.Finn MG.Fokin VV.Kolb HC.Sharpless KB. Angew. Chem. Int. Ed. 2005, 44: 3275 -
2a
Fieser LF.Campbell WP.Fry EM. J. Am. Chem. Soc. 1939, 61: 2206 -
2b
Takahashi I.Nomura A.Kitajima H. Synth. Commun. 1990, 20: 1569 -
2c
Kotha S.Mandal K. Tetrahedron Lett. 2004, 45: 2585 -
3a
Harwood LM.Oxford AJ.Thomson C. J. Chem. Soc., Chem. Commun. 1987, 1615 -
3b
Tan W.-F.Li W.-DZ.Li Y.-L. Synth. Commun. 2002, 32: 1077 -
3c
Anjaneyulu ASR.Isaa BM. J. Chem. Soc., Perkin Trans. 1 1991, 2089 - Aluminum(III) derivatives:
-
4a
Wipf P.Rodriguez S. Adv. Synth. Catal. 2002, 344: 434 -
4b
Maruoka K.Sato J.Banno H.Yamamoto H. Tetrahedron Lett. 1990, 31: 377 - Lanthanides salts:
-
4c
Sharma GVM.Ilangovan A.Sreenivas P.Mahalingam AK. Synlett 2000, 615 - Clays:
-
4d
Dauben WG.Cogen JM.Behar V. Tetrahedron Lett. 1990, 31: 3241 -
4e
Dintzner MR.Morse KM.McClelland KM.Coligado DM. Tetrahedron Lett. 2004, 45: 79 -
5a
Organobismuth Chemistry
Suzuki H.Matano Y. Elsevier; Amsterdam: 2001. -
5b
Gaspard-Iloughmane H.Le Roux C. Eur. J. Org. Chem. 2004, 2517 -
5c
Leonard NM.Wieland LC.Mohan RS. Tetrahedron 2002, 58: 8373 -
6a
Ogawa C.Azoulay S.Kobayashi S. Heterocycles 2005, 66: 201 -
6b
Ollevier T.Lavie-Compin G. Tetrahedron Lett. 2004, 45: 49 -
6c
Ollevier T.Lavie-Compin G. Tetrahedron Lett. 2002, 43: 7891 -
7a
Ollevier T.Nadeau E. Synlett 2006, 219 -
7b
Ollevier T.Desyroy V.Debailleul B.Vaur S. Eur. J. Org. Chem. 2005, 4971 -
7c
Kobayashi S.Ogino T.Shimizu H.Ishikawa S.Hamada T.Manabe K. Org. Lett. 2005, 7: 4729 -
7d
Ollevier T.Nadeau E. J. Org. Chem. 2004, 69: 9292 -
7e
Le Roux C.Ciliberti L.Laurent-Robert H.Laporterie A.Dubac J. Synlett 1998, 1249 -
7f
Ollevier T.Nadeau E.Eguillon J.-C. Adv. Synth. Catal. 2006, 348: 2080 -
7g
Ollevier, T.; Desyroy, V.; Nadeau, E. ARKIVOC, 2007, accepted
- 8
Leonard NM.Oswald MC.Freiberg DA.Nattier BA.Smith RC.Mohan RS. J. Org. Chem. 2002, 67: 5202 - 9
Ollevier T.Ba T. Tetrahedron Lett. 2003, 44: 9003 -
10a
Le Roux C.Dubac J. Synlett 2002, 181 -
10b
Ollevier T.Desyroy V.Asim M.Brochu M.-C. Synlett 2004, 2794 -
11a
Répichet S.Zwick A.Vendier L.Le Roux C.Dubac J. Tetrahedron Lett. 2002, 43: 993 -
11b
Labrouillère M.Le Roux C.Gaspard H.Laporterie A.Dubac J.Desmurs JR. Tetrahedron Lett. 1999, 40: 285 -
11c
Bi(OTf)3·4H2O was prepared from Bi2O3 according to reference 11a.
- 12
Ollevier T.Mwene-Mbeja TM. Tetrahedron Lett. 2006, 47: 4051 ; and references cited therein - 13
Parrish JP.Sudaresan B.Jung KW. Synth. Commun. 1999, 29: 4423 -
14a
De Renzi A.Panunzi A.Saporito A.Vitagliano A. J. Chem. Soc., Perkin Trans. 2 1983, 993 -
14b
Teng M.Duong TT.Johson AT.Klein ES.Wang L.Khalifa B.Chandraratna RAS. J. Med. Chem. 1997, 40: 2445 -
14c
Clemo GR.Ghatge ND. J. Chem. Soc. 1955, 4347 -
14d
Pochini A.Marchelli R.Boochi V. Gazz. Chim. Ital. 1975, 105: 1253 -
14e
Pisco L.Kordian M.Peseke K.Feist H.Michalik D.Estrada E.Carvalho J.Hamilton G.Rando D.Quincores J. Eur. J. Med. Chem. 2006, 41: 401 -
14f
Ferrari F.Delle Monache G.Alves De Lima R. Phytochemistry 1985, 24: 2753 -
14g
Anjaneyulu ASR.Isaa BM. J. Chem. Soc., Perkin Trans. 1 1991, 2089