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 2008(10): 1575-1579
DOI: 10.1055/s-2008-1072570
DOI: 10.1055/s-2008-1072570
PAPER
© Georg Thieme Verlag Stuttgart · New York
Efficient Palladium-Catalyzed Synthesis of Aminopyridyl Phosphonates from Bromopyridines and Diethyl Phosphite
Further Information
Received
15 January 2008
Publication Date:
27 March 2008 (online)
Publication History
Publication Date:
27 March 2008 (online)
Abstract
A general method for coupling aminopyridyl bromides with diethyl phosphite is reported. This efficient route is realized through the use of a palladium catalyst and triethylamine as base.
Key words
palladium - catalysis - phosphonates - cross-coupling - pyridyl halides
- For reviews, see:
-
1a
Muci AR.Buchwald SL. Top. Curr. Chem. 2002, 219: 131 -
1b
Hartwig JF. In Handbook of Organopalladium Chemistry for Organic Synthesis Vol. 1:Negishi E.-I. Wiley-Interscience; New York: 2002. -
1c
Beletskaya IP. Pure Appl. Chem. 1997, 69: 471 -
2a
Hirao T.Masunaga T.Ohshiro Y.Agawa T. Synthesis 1981, 56 -
2b
Hirao T.Masunaga T.Yamada N.Ohshiro Y.Agawa T. Bull. Chem. Soc. Jpn. 1982, 55: 909 -
2c
Petrakis KS.Nagabhushan TL. J. Am. Chem. Soc. 1987, 109: 2831 -
2d
Kabachnik MM.Solntseva MD.Izmer VV.Novikova ZS.Beletskaya IP. Russ. J. Org. Chem. 1998, 34: 93 -
2e
Defacqz N.de Bueger B.Touillaux R.Cordi A.Marchand-Brynaert J. Synthesis 1999, 1368 -
2f
Ngo HL.Lin W. J. Am. Chem. Soc. 2002, 124: 14298 - For Ni- or Cu-mediated coupling of aryl halides with trialkyl phosphites, see:
-
3a
Tavs P.Korte F. Tetrahedron 1967, 23: 4677 -
3b
Tavs P. Chem. Ber. 1970, 103: 2428 -
3c
Osuka A.Ohmasa N.Yoshida Y.Suzuki H. Synthesis 1983, 69 -
3d
Yuan C.Feng H. Synthesis 1990, 140 -
3e
Czech BP.Desai DH.Koszuk J.Czech A.Babb DA.Robison TW.Bartsch RA. J. Heterocycl. Chem. 1992, 29: 867 -
3f For Cu-promoted coupling of aryl halides with dialkyl phosphites, see:
Ogawa T.Usuki N.Ono N. J. Chem. Soc., Perkin Trans. 1 1998, 2953 -
3g For Cu-catalyzed coupling of aryl iodides with dialkyl phosphites, see:
Gelman D.Jiang L.Buchwald SL. Org. Lett. 2003, 5: 2315 -
3h For Cu-catalyzed reactions of diazonium salt with PCl3, see:
Freedman LD.Doak GO. J. Am. Chem. Soc. 1955, 77: 173 -
3i For Friedel-Crafts reaction of arenes with phosphorous derivatives, see:
Kosolapoff GM. J. Am. Chem. Soc. 1952, 74: 4119 -
3j For nucleophilic substitution reaction of activated aryl halides with sodium dialkylphosphites, see:
Boumekouez A.About-Jaudet E.Savignac NCP. J. Organomet. Chem. 1992, 440: 297 -
3k For SRN1 substitution reaction of aryl halides with sodium dialkylphosphites, see:
Beugelmans R.Chbani M. Bull. Soc. Chim. Fr. 1995, 132: 290 -
4a
Johansson T.Stawinski J. Chem. Commun. 2001, 2564 -
4b
Ayyappan P.Evans OR.Foxman BM.Wheeler KA.Warren TH.Lin W. Inorg. Chem. 2001, 40: 5954 -
4c
Ayyappan P.Evans OR.Cui Y.Wheeler KA.Lin W. Inorg. Chem. 2002, 41: 4978 -
4d
Ziessel RF.Charbonniere LJ.Mameri S.Camerel F. J. Org. Chem. 2005, 14: 9835 - 5
Bulot JJ.Aboujaoude EE.Collignon N.Savignac P. Phosphorus, Sulfur Relat. Elem. 1984, 21: 197 - 6
Penicaud V.Odobel F.Bujoli B. Tetrahedron Lett. 1998, 39: 3689 -
7a
Yates FS. Pyridines and their Benzo Derivatives: (vi) Applications, In Comprehensive Heterocyclic Chemistry. The Structure, Reactions, Synthesis and Uses of Heterocyclic Compounds Vol. 2:Katritzky AR.Rees CW. Pergamon Press; Oxford: 1984. -
7b
Pyridine and its Derivatives
Part 5:
Newkome GR. Wiley-Interscience; New York: 1984. -
7c
The Merck Index: An Encyclopedia of Chemicals, Drugs and Biologicals
Merck Research Laboratories Division of Merck & CO., INC.;
Whitehouse Station NJ:
2001.
- 8
Pierrat P.Gros PC.Fort Y. J. Comb. Chem. 2005, 7: 879 - 9
Gooßen LJ.Dezfuli MK. Synlett 2005, 445