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Synthesis 2009(7): 1220-1223
DOI: 10.1055/s-0028-1087996
DOI: 10.1055/s-0028-1087996
PSP
© Georg Thieme Verlag
Stuttgart ˙ New York
A New Atom-Economical and Selective Synthesis of Secondary and Tertiary Alkylamines by Means of Cp*Iridium Complex Catalyzed Multiple N-Alkylation of Ammonium Salts with Alcohols without Solvent
Further Information
Received
13 November 2008
Publication Date:
06 March 2009 (online)
Publication History
Publication Date:
06 March 2009 (online)
Abstract
A new atom-economical and selective synthetic method for secondary and tertiary alkylamines has been achieved by means of (pentamethylcyclopentadienyl)iridium (Cp*Ir) complex catalyzed multiple N-alkylations of ammonium salts with primary and secondary alcohols without solvent.
Key words
ammonium salt - alcohol - amine - N-alkylation - iridium complex
- For example:
-
1a
Salvatore RN.Yoon CH.Jung KW. Tetrahedron 2001, 57: 7785 -
1b
Chiappe C.Pieraccini D. Green Chem. 2003, 5: 193 -
2a
Fujita K.Li Z.Ozeki N.Yamaguchi R. Tetrahedron Lett. 2003, 44: 2687 -
2b
Fujita K.Fujii T.Yamaguchi R. Org. Lett. 2004, 6: 3525 -
2c
Fujita K.Enoki Y.Yamaguchi R. Org. Synth. 2006, 83: 217 -
2d
Fujita K.Enoki Y.Yamaguchi R. Tetrahedron 2008, 64: 1943 -
3a
Fujita K.Yamaguchi R. Synlett 2005, 560 -
3b
Fujita K.Yamaguchi R. In Iridium Complexes in Organic SynthesisOro L. A.Claver C. Wiley-VCH; Weinheim: 2009. Chap 5. p.107-143 - 4 For an earlier review concerning
the use of ammonia in catalytic reactions, see:
Roundhill DM. Chem. Rev. 1992, 92: 1 - 5
Prinz T.Driessen-Hölscher B. Chem. Eur. J. 1999, 5: 2069 -
6a
Kitamura M.Lee D.Hayashi S.Tanaka S.Yoshimura M. J. Org. Chem. 2002, 67: 8685 -
6b
Gross T.Seayad AM.Ahmad M.Beller M. Org. Lett. 2002, 4: 2055 -
6c
Ogo S.Makihara N.Kaneko Y.Watanabe Y. Organometallics 2001, 20: 4903 -
7a
Lang F.Zewge D.Houpis IN.Volante RP. Tetrahedron Lett. 2001, 42: 3251 -
7b
Shen Q.Hartwig JF. J. Am. Chem. Soc. 2006, 128: 10028 -
7c
Surry DS.Buchwald SL. J. Am. Chem. Soc. 2007, 129: 10354 ; and references cited therein - 8 Very recently, Ru-catalyzed tri-N-alkylation
of NH4OAc with PhCH2OH affording tribenzylamine
has been reported, although only one reaction using NH4OAc
has been shown and the yield of tribenzylamine is moderate, see:
Hamid MHSA.Williams JMJ. Tetrahedron Lett. 2007, 48: 8263 - 9 For a preliminary report, see:
Yamaguchi R.Kawagoe S.Asai C.Fujita K. Org. Lett. 2008, 10: 181 - 10
Ball RG.Graham WAG.Heinekey DM.Hoyano JK.McMaster AD.Mattson BM.Michel ST. Inorg. Chem. 1990, 29: 2023 - 11
The Aldrich Library of ¹³C
and ¹H FT NMR Spectra
1st ed., Vol.
2:
Pouchert C. J.Behnke J. Aldrich Chemical Company Inc.; Milwaukee: 1993. p.590B -
12a
Eggert H.Djerassi C. J. Am. Chem. Soc. 1973, 95: 3710 -
12b
The Aldrich Library
of ¹³C and ¹H FT
NMR Spectra
1st ed., Vol. 1:
Pouchert C. J.Behnke J. Aldrich Chemical Company Inc.; Milwaukee: 1993. p.485B - 13
The Aldrich Library of ¹³C
and ¹H FT NMR Spectra
1st ed., Vol.
1:
Pouchert C. J.Behnke J. Aldrich Chemical Company Inc.; Milwaukee: 1993. p.478A - 14
The Aldrich Library of ¹³C
and ¹H FT NMR Spectra
1st ed., Vol.
1:
Pouchert C. J.Behnke J. Aldrich Chemical Company Inc.; Milwaukee: 1993. p.508C