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 2008(2): 267-271
DOI: 10.1055/s-2007-1000859
DOI: 10.1055/s-2007-1000859
PAPER
© Georg Thieme Verlag Stuttgart · New YorkPhosphomolybdic Acid: Mild and Efficient Catalyst for Acetylation of Alcohols, Phenols, and Amines under Solvent-Free Conditions
Weitere Informationen
Received
19 September 2007
Publikationsdatum:
18. Dezember 2007 (online)
Publikationsverlauf
Publikationsdatum:
18. Dezember 2007 (online)

Abstract
Phosphomolybdic acid (PMA) has been found to be a simple and efficient catalyst for the acetylation of alcohols, phenols, and amines. Acetylation reactions with acetic anhydride (1.0 equiv) proceed in excellent yield in the presence of a catalytic amount (0.2 mol%) of PMA at ambient temperature within a relatively short reaction time (<10 min). Structurally diverse alcohols, phenols, and amines undergo acetylation under solvent-free conditions.
Key words
acetylation - phosphomolybdic acid - alcohols - amines - green catalysis
- 1a
Green TW.Wuts PGM. In Protective Groups in Organic Synthesis 3rd ed.: Wiley; New York: 1999. p.150 - 1b
Otera J. Chem. Rev. 1993, 93: 1449 - 1c
Franklin AS. J. Chem. Soc., Perkin Trans. 1 1998, 2451 - 1d
Franklin AS. J. Chem. Soc., Perkin Trans. 1 1999, 3537 - 2a
Zhdanov RI.Zhenodarova SM. Synthesis 1975, 222 - 2b
Strok G.Takahashi T.Kawamoto I.Suzuki T. J. Am. Chem. Soc. 1978, 100: 8272 - 2c
Dauban WG.Bune RA.Gerdes JM.Henger KE.Cunningham AM.Ottoboni TB. Tetrahedron Lett. 1983, 24: 5709 - 3a
Hofle G.Steglich W.Vorbruggen H. Angew. Chem., Int. Ed. Engl. 1978, 17: 569 - 3b
Steglich W.Hofle G. Angew. Chem., Int. Ed. Engl. 1969, 8: 981 - 4a
Vedejs E.Diver ST. J. Am. Chem. Soc. 1993, 115: 3358 - 4b
Vedejs E.Bennett NS.Conn LM.Diver ST.Gingras M.Lin S.Oliver PA.Petrson MJ. J. Org. Chem. 1993, 58: 7286 - 5a
Iqbal J.Srivastava RR. J. Org. Chem. 1992, 57: 2001 ; and references cited therein - 5b
Chandrasekhar S.Ramaeshandar TT. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2004, 43: 83 ; and references cited therein - 5c
Backer RH.Bordewell FG. Org. Synth. 1995, 3: 141 - 5d
Chakraborti AK.Gulhane R. Synlett 2004, 657 - 5e
Chakraborti AK.Gulhane R. Tetrahedron Lett. 2003, 44: 3521 - 5f
Shirini F.Zolfigol MA.Abedini M. Monatsh. Chem. 2004, 135: 279 - 5g
Bosco JWJ.Saikia AK. Chem. Commun. 2004, 1116 - 5h
Bosco JWJ.Agrahari A.Saikia AK. Tetrahedron Lett. 2006, 47: 4065 - 5i
Phukan P. Tetrahedron Lett. 2004, 45: 4785 - 5j
Tale RH.Adude RN. Tetrahedron Lett. 2006, 47: 7263 - 5k
Heravi MM.Behbahani KF.Bamoharram FF. J. Mol. Catal. A: Chem. 2006, 253: 16 - 6a
Ishihara K.Kubota M.Kurihara H.Yamamoto H. J. Org. Chem. 1996, 61: 4560 - 6b
Orita A.Tanahashi C.Kakuda A.Otera J. Angew. Chem. Int. Ed. 2000, 39: 2877 - 6c
Saravanan P.Singh VK. Tetrahedron Lett. 1999, 40: 2611 - 6d
Chauhan KK.Frost CG.Love I.Waite D. Synlett 1999, 1743 - 6e
Kamal A.Khan MA.Reddy SY.Srikant VV.Krishnaji T. Tetrahedron Lett. 2007, 48: 3813 - 6f
Dalpozzo R.De Nino A.Maiuolo L.Procopio A.Nardi M.Bartoli G.Romeo R. Tetrahedron Lett. 2003, 44: 5621 - 6g
Alleti R.Perambudura M.Samantha S.Reddy VP. J. Mol. Catal. A: Chem. 2005, 226: 57 - 6h
Antonio PR.Dalpozzo R.De Nino A.Maiuolo L.Russo B.Sindona G. Adv. Synth. Catal. 2004, 346: 1465 - 6i
Herari M.Behbahani F. K.Bamoharram F. F. J. Mol. Catal. 2006, 253: 16 - 7a
Nakae Y.Kusaki I.Sato T. Synlett 2001, 1584 - 7b
Kondasamy JK.Chaand DK. J. Mol. Catal. A: Chem. 2006, 255: 275 - 7c
Bartoli G.Bosco M.Dalpozzo R.Marcantoni E.Massaccesi M.Rinaldi S.Sambri L. Synlett 2003, 39 - 7d
Heravi MM.Behbahani FK.Shoar RH.Oskooie HA. Catal. Commun. 2006, 7: 136 - 7e
Chakraborti AK.Gulhane FK. Chem. Commun. 2003, 1896 - 8a
Li A.-X.Li T.-S.Ding T.-H. Chem. Commun. 1997, 1389 - 8b
Khazaei A.Rostami A.Tanbakouchian Z.Zinati Z. Catal. Commun. 2006, 7: 214 - 8c
Reddy TS.Narasimhulu MN.Suryakiran K.Mahesh C.Ashalatha K.Venkateswarlu Y. Tetrahedron Lett. 2006, 47: 6825 - 8d
Kumar P.Pandey RK.Bodas MS.Dongare MK. Synlett 2001, 206 - 8e
Zolfigol MA.Khazaei A.Choghamarani AG.Rostai A.Hajjami M. Catal. Commun. 2006, 7: 399 - 8f
Kumareswaran R.Pachamuthu K.Vakar YD. Synlett 2000, 1652 - 8g
Grasa GA.Guveli T.Singh R.Nolan SP. J. Org. Chem. 2003, 68: 2812 - 8h
Grasa GA.Kissling RM.Nolan SP. Org. Lett. 2002, 4: 3583 - 9a
Schumacher JC. Perchlorates - Their Properties, Manufacture, and Use ACS Monograph Series, Reinhold; New York: 1996. - 9b
Long J. Chem. Health Safety 2002, 9: 12 - 10a
Kozhevnikov IV. Chem. Rev. 1998, 98: 171 - 10b
Mizuno N.Misono M. Chem. Rev. 1998, 98: 199 - 11
Makoto M.Izumi O.Gaku K.Atsushi A. Pure Appl. Chem. 2000, 72: 1305 - 12a
Izumi Y.Hasebe R.Urabe K. J. Catal. 1983, 84: 402 - 12b
Kozhevnikov IV. Russ. Chem. Rev. 1987, 56: 811 - 12c
Okuhara T.Mizuno N.Misono M. Adv. Catal. 1996, 41: 113 - 13
Izumi Y.Urabe K.Onaka M. Zeolite Clay and Heteropoly Acid in Organic Reactions Kodansha/VCH; Tokyo: 1992. p.99 - 14
Kaur J.Griffin K.Harrison B.Kozhevnikov IV. J. Catal. 2002, 208: 448 - 15
Kozhevnikova EF.Derouane EG.Kozhevnikov IV. Chem. Commun. 2002, 1178 - 16
Firouzabadi H.Iranpoor N.Amani K. Synthesis 2003, 408 - 17
Kishore Kumar GD.Baskaran S. Synlett 2004, 1719 - 18
Kishore Kumar GD.Baskaran S. J. Org. Chem. 2005, 70: 4520