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(15): 2347-2352
DOI: 10.1055/s-2008-1067160
DOI: 10.1055/s-2008-1067160
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Pd(OAc)2-Catalyzed Aminocarbonylation of Aryl Iodides with Aromatic or Aliphatic Amines in Water
Further Information
Received
31 March 2008
Publication Date:
08 July 2008 (online)
Publication History
Publication Date:
08 July 2008 (online)
Abstract
An efficient ligand-free protocol has been developed for the amincocarbonylation of aryl iodides with aromatic/aliphatic amines using palladium(II) acetate as a catalyst in water under milder operating conditions. The system tolerated a wide variety of hindered and functionalized aryl iodides/amines and afforded the desired amides in excellent yields at low catalyst concentration.
Key words
carbonylation - aryl iodides - amines - amides - palladium
-
1a
Valentine D.Tilley JW.LeMahieu RA. J. Org. Chem. 1981, 46: 4614 -
1b
Cassar L.Foa M.Gardano A. J. Organomet. Chem. 1976, 121: 55 -
1c
Grushin VV.Alper H. J. Chem. Soc., Chem. Commun. 1992, 611 -
1d
Beletskaya IP.Lapidus AL.Petrovskii KB. Russ. J. Org. Chem. 1998, 34: 1464 -
1e
Lin YS.Yamamoto A. J. Organomet. Chem. 2002, 645: 152 -
2a
Schoenberg A.Heck RF. J. Org. Chem. 1974, 39: 3327 -
2b
Perry RJ.Wilson BD. Organometallics 1994, 13: 3346 -
2c
Takahashi T.Inoue H.Tomida S.Doi T.Bray AM. Tetrahedron Lett. 1999, 40: 7843 -
2d
Magerlein W.Indolese AF.Beller M. J. Organomet. Chem. 2002, 641: 30 -
3a
Schoenberg A.Bartoletti I.Heck RF. J. Org. Chem. 1974, 39: 3318 -
3b
Ben-David Y.Portnoy M.Milstein D. J. Am. Chem. Soc. 1989, 111: 8742 -
3c
Yang J.Haynes A.Maitlis PM. Chem. Commun. 1999, 179 -
3d
Calo V.Giannoccaro P.Nacci A.Monopoli A. Tetrahedron Lett. 2001, 42: 3299 -
3e
Magerlein W.Beller M.Indolese AF. J. Mol. Catal. A: Chem. 2000, 156: 213 -
4a
Ben-David Y.Portnoy M.Milstein D. J. Chem. Soc., Chem. Commun. 1989, 1816 -
4b
Okano T.Harada N.Kiji J. Bull. Chem. Soc. Jpn. 1994, 67: 2329 - 5
Stille JK. Pure Appl. Chem. 1985, 57: 1771 -
6a
Colquhoun HM.Thompson DJ.Twigg MV. Carbonylation Direct Synthesis of Carbonyl Compounds Plenum Press; New York: 1991. -
6b
Tsuji J. Palladium Reagents and Catalysis Wiley; Chichester: 1995. -
6c
Heck RF. Palladium Reagents in Organic Synthesis Academic Press; New York: 1985. - 7
Schoenberg A.Heck RF. J. Org. Chem. 1974, 39: 3327 - 8
Cai M.Huang Y.Hu R.Song C. J. Mol. Catal. A: Chem. 2004, 212: 151 - 9
Cai M.Zhao H.Huang Y. J. Mol. Catal. A: Chem. 2005, 238: 41 - 10
Skoda-Foldes R.Takacs E.Horvath J.Tuba Z.Kollar L. Green Chem. 2003, 5: 643 - 11
Miller PM.Long NJ.Mello AJ.Vilar R.Passchier J.Gee A. Chem. Commun. 2006, 546 - 12
Martinelli JR.Clark TP.Watson DA.Munday RH.Buchwald SL. Angew. Chem. Int. Ed. 2007, 46: 8460 - 13
Csajági C.Borcsek B.Niesz K.Kovács I.Székelyhidi Z.Bajkó Z.Ürge L.Darvas F. Org. Lett. 2008, 10: 1589 -
14a
Ionic Liquids in Synthesis
Wasserscheid P.Welton T. Wiley-VCH; Weinheim: 2003. -
14b
Chemical Synthesis
Using Supercritical Fluids
Jessop PG.Leitner W. Wiley-VCH; Weinheim: 1999. -
14c
Organic Reactions
in Water
Lindström UM. Blackwell; Oxford: 2007. -
14d
Tanaka K. Solvent-Free Organic Synthesis Wiley-VCH; Weinheim: 2003. -
15a
Li C.-J. Chem. Rev. 2005, 105: 3095 -
15b
Liang B.Huang M.You Z.Xiong Z.Lu K.Fathi R.Chen J.Yang Z. J. Org. Chem. 2005, 70: 6097 -
15c
Palimkar SS.Lahoti RJ.Srinivasan KV. Green Chem. 2007, 9: 146 -
15d
Chakraborti AK.Rudrawar S.Jadhav KB.Kaur G.Chankeshwara SV. Green Chem. 2007, 9: 1335 -
16a
Tambade PJ.Patil YP.Bhanushali MJ.Bhanage BM. Tetrahedron Lett. 2008, 49: 2221 -
16b
Tambade PJ.Patil YP.Nandurkar NS.Bhanage BM. Synlett 2008, 886