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 2005(4): 595-599
DOI: 10.1055/s-2005-861789
DOI: 10.1055/s-2005-861789
PAPER
© Georg Thieme Verlag Stuttgart · New York
Aluminium Triflate [Al(OTf)3] as a Recyclable Catalyst for the Conversion of α-Hydroxyphosphonates, Alcohols and Phenols to Their Corresponding O-Silylated Products with Hexamethyldisilazane (HMDS)
Further Information
Received
19 September 2004
Publication Date:
18 January 2005 (online)
Publication History
Publication Date:
18 January 2005 (online)
Abstract
Al(OTf)3 as a recyclable catalyst conducts the efficient conversion of various types of α-hydroxyphosphonates to their corresponding α-trimethysilyloxyphosphonates with HMDS in the absence of solvent at room temperature. The general applicability of the catalyst under solvent-free conditions is demonstrated by applying it for the successful silylation of alcohols and phenols with HMDS in high yields.
Keywords
α-hydroxyphosphonates - solvent-free - aluminium triflate - α-acetyloxyphosphonates - alcohols - phenols
-
1a
Firouzabadi H.Iranpoor N.Sobhani S. Tetrahedron Lett. 2002, 43: 3653 -
1b
Firouzabadi H.Iranpoor N.Sobhani S.Ghassamipour S.Amoozgar Z. Tetrahedron Lett. 2003, 44: 891 -
1c
Firouzabadi H.Iranpoor N.Sobhani S.Ghassamipour S. J. Organomet. Chem. 2004, 689: 3197 -
2a
Kabachnik MM.Synatkova EV.Novikova ZS.Abramova GL.Rozhkova NG.Andreeva EI. Vestn. Mosk. Univ., Khim. 1990, 31: 384 -
2b
Birum GH, andRichardson GA. inventors; Monsanto Chem. Co; US Patent, 3113139. ; Chem. Abstr. 1964, 60, 5551d -
2c
Olah GA.Wu A. J. Org. Chem. 1991, 56: 902 - 3
Koenigkramer RE.Zimmer H. Tetrahedron Lett. 1980, 21: 1017 -
4a
Sekine M.Nakajima M.Hata T. Tetrahedron Lett. 1979, 4475 -
4b
Hata T.Hashisume A.Nakajima M.Sekine M. Tetrahedron Lett. 1978, 363 - 5
Sekine M.Nakajima M.Kume A.Hashizume A. Bull. Chem. Soc. Jpn. 1982, 55: 218 - 6
Evans DA.Hurst KM.Truesdale LK.Takacs JM. Tetrahedron Lett. 1977, 29: 2495 - 7
Sekiguchi A.Ikeno M.Ando W. Bull. Chem. Soc. Jpn. 1978, 51: 337 -
8a
Texier-Boullet F.Foucaud A. Synthesis 1982, 916 -
8b
Baraldi PG.Guarneri M.Moroder F.Polloni GP.Simoni D. Synthesis 1982, 653 - 9
Lebedev EP.Mizhiritskii MD.Baburina VA.Mironov VF.Ofitserov EN. Zh. Obshch. Khim. 1979, 49: 1731 -
10a
Iranpoor N.Shekarriz M. Bull. Chem. Soc. Jpn. 1999, 72: 455 -
10b
Firouzabadi H.Karimi B.Eslami S. Tetrahedron Lett. 1999, 40: 4055 -
10c
Firouzabadi H.Eslami S.Karimi B. Bull. Chem. Soc. Jpn. 2001, 74: 2401 -
10d
Firouzabadi H.Iranpoor N.Kohmareh G. Synth. Commun. 2003, 33: 167 - 11
Olah GA.Farooq O.Farnia SMF.Olah JA. J. Am. Chem. Soc. 1990, 110: 2560 - 12
Ernst A.Karola H.Hermann M. Synthesis 1990, 323 - 13
Zhonghua L.Chuanfang Z. Main Group Met. Chem. 1995, 18: 669 - 14
Sekine M.Nakajima M.Kume A.Hashizume A. Bull. Chem. Soc. Jpn. 1982, 55: 224 - 15
Auge J.Leory F. Tetrahedron Lett. 1996, 37: 7715 - 16
Imamoto T.Koide Y.Hiyama S. Chem. Lett. 1990, 1445 - 17
Nishizawa M.Takenaka H.Nishide H.Hayashi Y. Tetrahedron Lett. 1983, 24: 2581 - 18
Jenkins CL.Kochi JK. J. Am. Chem. Soc. 1972, 94: 843 - 19
Corey EJ.Shimoji K. Tetrahedron Lett. 1983, 24: 169 -
20a
Firouzabadi H.Karimi B. Synth. Commun. 1993, 23: 1633 -
20b
Firouzabadi H.Sardarian AR.Khayat Z.Karimi B.Tangestaninejad S. Synth. Commun. 1997, 27: 2709 - 21
Green TW.Wuts PGM. Protective Groups in Organic Synthesis 3rd ed.: Wiley; New York: 1999. and references cited therein