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DOI: 10.1055/s-2008-1078421
Efficient Direct Alkynylation of Trifluoromethyl Ketones Catalyzed by AgF in Water and Organic Solvents
Publikationsverlauf
Publikationsdatum:
16. Mai 2008 (online)
Abstract
A general and efficient method for the direct alkynylation of trifluoropyruvate and trifluoroacetophenone in water was developed by using AgF and PCy3 as a catalyst. The ligand enhanced the catalyst activity significantly. The reaction in water is comparable to the one carried out in organic solvents.
Key words
direct alkynylation - trifluoromethyl ketones - silver fluoride
- 1
Anastas PT.Warner JC. Green Chemistry: Theory and Practice Oxford University Press; Oxford: 1998. - For representative reviews, see:
-
2a
Li C.-J. Chem. Rev. 2005, 105: 3095 -
2b
Li C.-J.Chan T.-H. Tetrahedron 1999, 55: 11149 -
2c
Li C.-J. Tetrahedron 1996, 52: 5643 -
2d
Chan T.-H.Isaac MB. Pure Appl. Chem. 1996, 68: 919 -
2e
Li C.-J.Chan T.-H. Organic Reactions in Aqueous Media John Wiley and Sons; New York: 1997. -
2f
Organic Synthesis in Water
Grieco PA. Thomson Science; Glasgow: 1998. -
2g
Li C.-J. Chem. Rev. 1993, 93: 2023 -
2h
Li C.-J.Chan T.-H. Comprehensive Organic Reactions in Aqueous Media John Wiley and Sons; New York: 2007. -
2i
Organic Reactions in Water
Lindstrom UM. Blackwell Publishing; Oxford: 2007. -
3a
Reddy MS.Narender M.Nageawar YVD.Rao KR. Synth. Commun. 2007, 37: 1983 -
3b
Li J.-M.Zha Z.-G.Sun L.-L.Zhang Y.Wang Z.-Y. Chem. Lett. 2006, 35: 498 -
3c
Chaudhuri MK.Dehury SK.Hussain S. Tetrahedron Lett. 2005, 46: 6247 -
3d
Zha Z.-G.Xie Z.Zhou C.-L.Chang M.-X.Wang Z.-Y. New J. Chem. 2003, 27: 1297 -
3e
Li C.-J.Meng Y.Yi X.-H. J. Org. Chem. 1998, 63: 7498 -
3f
Nokami J.Otera J.Sudo T.Okawara R. Organometallics 1983, 2: 191 -
4a
Issac MB.Chan T.-H. J. Chem. Soc., Chem. Commun. 1995, 1003 -
4b
Yi X.-H.Meng Y.Li C.-J. Chem. Commun. 1998, 449 -
5a
Zhou C.-L.Wang Z.-Y. Synthesis 2005, 1649 -
5b
Bieber LW.Storch EC.Malvestiti I.Sila MF. Tetrahedron Lett. 1998, 39: 9393 -
6a
Petasis NA.Zavialov IA. J. Am. Chem. Soc. 1997, 119: 445 -
6b
Ueda M.Miyaura N. J. Org. Chem. 2000, 65: 4450 -
6c
Hayashi T.Ishigedani M. J. Am. Chem. Soc. 2000, 122: 976 -
6d
Li C.-J.Meng Y. J. Am. Chem. Soc. 2000, 122: 9538 - 7
Keh CCK.Wei C.Li C.-J. J. Am. Chem. Soc. 2003, 125: 4062 - 8
Chan T.-H.Li C.-J.Wei Z.-Y. J. Chem. Soc., Chem. Commun. 1990, 505 -
9a
Yao X.Li C.-J. Org. Lett. 2005, 7: 4395 -
9b
Wei C.Mague JT.Li C.-J. Proc. Natl. Acad. Sci. U.S.A. 2004, 101: 5749 -
9c
Wei C.Li C.-J. J. Am. Chem. Soc. 2003, 125: 9584 -
9d
Wei C.Li Z.Li C.-J. Org. Lett. 2003, 5: 4473 -
9e
Wei C.Li C.-J. Green Chem. 2002, 4: 39 -
9f
Wei C.Li C.-J. J. Am. Chem. Soc. 2002, 124: 5638 -
9g
Li C.-J.Wei C. Chem. Commun. 2002, 268 -
9h
Zhang J.Wei C.Li C.-J. Tetrahedron Lett. 2002, 43: 5731 -
9i
Huang B.Yao X.Li C.-J. Adv. Synth. Catal. 2006, 348: 1528 -
9j
Yao X.Li C.-J. Org. Lett. 2006, 8: 1953 - For recent examples, see:
-
10a
Asano Y.Hara K.Ito H.Sawamura M. Org. Lett. 2007, 9: 3901 -
10b
Colombo F.Benaglia M.Orlandi S.Usuelli F.Celentano G. J. Org. Chem. 2006, 71: 2064 -
10c
Arimitsu S.Hammond GB. J. Org. Chem. 2006, 71: 8665 -
10d
Gommermann N.Koradin C.Polborn K.Knochel P. Angew. Chem. Int. Ed. 2003, 42: 5763 -
10e
Koradin C.Gommermann N.Polborn K.Knochel P. Chem. Eur. J. 2003, 9: 2797 -
10f
Lu G.Li X.Chan WL.Chan ASC. Chem. Commun. 2002, 172 -
10g
Chen ZL.Xiong WN.Jiang B. Chem. Commun. 2002, 2098 -
10h
Koradin C.Polborn K.Knochel P. Angew. Chem. Int. Ed. 2002, 41: 2535 -
10i
Carreira EM. Acc. Chem. Res. 2000, 33: 373 ; and references therein - 11 For alkynylation of trifluoroacetophenone, see:
Motoki R.Kanai M.Shibasaki M. Org. Lett. 2007, 9: 2997 - 12
Hiyama T. Organo Fluorine Compounds: Chemistry and Applications Springer; Berlin: 2000. - Trifluoropyruvates were used as substrates for catalytic Friedel-Crafts reactions, ene reactions, and aldol reactions. For examples, see:
-
13a
Ogawa S.Shibata N.Inagaki J.Nakamura S.Toru T.Shiro M. Angew. Chem. Int. Ed. 2007, 45: 8525 -
13b
Zhao JL.Liu L.Sui Y.Liu YL.Wang D.Chen YJ. Org. Lett. 2006, 8: 6127 -
13c
Zhao JL.Liu L.Zhang HB.Wu YC.Wang D.Chen YJ. Tetrahedron Lett. 2006, 47: 2511 -
13d
Bandini M.Melloni A.Umani-Ronchi A. Angew. Chem. Int. Ed. 2004, 43: 550 -
13e
Gathergood N.Juhl K.Poulsen TB.Thordrup K.Jørgensen KA. Org. Biomol. Chem. 2004, 2: 1077
References and Notes
Representative Experimental Procedure
A nitrogen-flushed 10 mL flask equipped with a magnetic stirrer and a septum was charged with AgF (6.3 mg, 0.05 mmol) and PCy3 (14 mg, 0.05 mmol). Ethyl 3,3,3-trifluoro-pyruvate (85 mg, 0.5 mmol), alkyne (2 equiv), and H2O (0.5 mL) were added by using a syringe. The reaction mixture was stirred for 1-2 d at r.t. and extracted with Et2O. The organic solvent was evaporated and the residue was purified by column chromatography (SiO2, hexane-EtOAc) and characterized by means of 1H NMR, 13C NMR, IR, and HRMS.