Iridium-Catalyzed Condensation
of Primary Amines To Form Secondary Amines

Linda L. R. Lorentz-Petersen; Paw Jensen; Robert Madsen

doi:10.1055/s-0029-1217058

SHORTPAPER

Iridium-Catalyzed Condensation of Primary Amines To Form Secondary Amines

Linda L. R. Lorentz-Petersen, Paw Jensen, Robert Madsen*
Department of Chemistry, Building 201, , Technical University of Denmark, 2800 Kgs. Lyngby, Denmark
Fax: +45(4593)3968; e-Mail: rm@kemi.dtu.dk;

Abstract

Alle Artikel dieser Rubrik

Abstract

Symmetric secondary amines are readily obtained by heating a neat primary amine with 0.5 mol% of bis(dichloro[η⁵-pentamethylcyclopentadienyl]iridium). The products are isolated by direct distillation in good yields.

Key words

amines - dimerizations - homogeneous catalysis - hydrogen transfer - iridium

Volltext

Referenzen

References

<A NAME="RT14309SS-1A">1a</A> Lawrence SA. Amines: Synthesis, Properties and Applications Cambridge University Press; Cambridge: 2004.

<A NAME="RT14309SS-1B">1b</A> Salvatore RN. Yoon CH. Jung KW. Tetrahedron 2001, 57: 7785

<A NAME="RT14309SS-2A">2a</A> Singh CB. Kavala V. Samal AK. Patel BK. Eur. J. Org. Chem. 2007, 1369

<A NAME="RT14309SS-2B">2b</A> Salvatore RN. Nagle AS. Jung KW. J. Org. Chem. 2002, 67: 674

<A NAME="RT14309SS-3A">3a</A> Tripathi RP. Verma SS. Pandey J. Tiwari VK. Curr. Org. Chem. 2008, 12: 1093

<A NAME="RT14309SS-3B">3b</A> Abdel-Magid AF. Mehrman SJ. Org. Process Res. Dev. 2006, 10: 971

<A NAME="RT14309SS-4">4</A> Kan T. Fukuyama T. Chem. Commun. 2004, 353

<A NAME="RT14309SS-5A">5a</A> Hartwig JF. Acc. Chem. Res. 2008, 41: 1534

<A NAME="RT14309SS-5B">5b</A> Surry DS. Buchwald SL. Angew. Chem. Int. Ed. 2008, 47: 6338

<A NAME="RT14309SS-6A">6a</A> Nacario R. Kotakonda S. Fouchard DMD. Tillekeratne LMV. Hudson RA. Org. Lett. 2005, 7: 471

<A NAME="RT14309SS-6B">6b</A> Sajiki H. Ikawa T. Hirota K. Org. Lett. 2004, 6: 4977

<A NAME="RT14309SS-7A">7a</A> Núnez Magro AA. Eastham GR. Cole-Hamilton DJ. Chem. Commun. 2007, 3154

<A NAME="RT14309SS-7B">7b</A> Hanada S. Ishida T. Motoyama Y. Nagashima H. J. Org. Chem. 2007, 72: 7551

<A NAME="RT14309SS-8A">8a</A> Blank B. Michlik S. Kempe R. Chem. Eur. J. 2009, 15: 3790

<A NAME="RT14309SS-8B">8b</A> Hamid MHSA. Allen CL. Lamb GW. Maxwell AC. Maytum HC. Watson AJA. Williams JMJ. J. Am. Chem. Soc. 2009, 131: 1766

<A NAME="RT14309SS-8C">8c</A> Fujita K.-i. Enoki Y. Yamaguchi R. Tetrahedron 2008, 64: 1943

<A NAME="RT14309SS-8D">8d</A> Yamaguchi R. Kawagoe S. Asai C. Fujita K.-i. Org. Lett. 2008, 10: 181

<A NAME="RT14309SS-8E">8e</A> Hollmann D. Tillack A. Michalik D. Jackstell R. Beller M. Chem. Asian J. 2007, 2: 403

<A NAME="RT14309SS-9A">9a</A> Prades A. Corberán R. Poyatos M. Peris E. Chem. Eur. J. 2008, 14: 11474

<A NAME="RT14309SS-9B">9b</A> Hollmann D. Bähn S. Tillack A. Beller M. Chem. Commun. 2008, 3199

<A NAME="RT14309SS-9C">9c</A> Bähn S. Hollmann D. Tillack A. Beller M. Adv. Synth. Catal. 2008, 350: 2099

<A NAME="RT14309SS-9D">9d</A> Hollmann D. Bähn S. Tillack A. Beller M. Angew. Chem. Int. Ed. 2007, 46: 8291

With Pt/C and Al, see:

<A NAME="RT14309SS-10A">10a</A> Miyazawa A. Saitou K. Tanaka K. Gädda TM. Tashiro M. Prakash GKS. Olah GA. Tetrahedron Lett. 2006, 47: 1437

With PtCl₂(PPh₃)₂ and SnCl₂˙2H₂O, see:

<A NAME="RT14309SS-10B">10b</A> Tsuji Y. Shida J. Takeuchi R. Watanabe Y. Chem. Lett. 1984, 889

With Pd/C, see:

<A NAME="RT14309SS-10C">10c</A> Murahashi S.-I. Yoshimura N. Tsumiyama T. Kojima T. J. Am. Chem. Soc. 1983, 105: 5002

With RuCl₂(PPh₃)₃, see:

<A NAME="RT14309SS-10D">10d</A> Khai BT. Concilio C. Porzi G. J. Organomet. Chem. 1981, 208: 249

With Raney nickel, see:

<A NAME="RT14309SS-10E">10e</A> De Angelis F. Grgurina I. Nicoletti R. Synthesis 1979, 70

<A NAME="RT14309SS-11">11</A> Largeron M. Fleury M.-B. Org. Lett. 2009, 11: 883

<A NAME="RT14309SS-12">12</A> Nordstrøm LU. Madsen R. Chem. Commun. 2007, 5034

<A NAME="RT14309SS-13">13</A> Katritzky AR. Zhao X. Hitchings GJ. Synthesis 1991, 703

<A NAME="RT14309SS-14">14</A> Juday R. Adkins H. J. Am. Chem. Soc. 1955, 77: 4559

<A NAME="RT14309SS-15">15</A> Anastasi C. Hantz O. De Clercq E. Pannecouque C. Clayette P. Dereuddre-Bosquet N. Dormont D. Gondois-Rey F. Hirsch I. Krau J.-L. J. Med. Chem. 2004, 47: 1183

<A NAME="RT14309SS-16">16</A> Nicolaou KC. Mathison CJN. Montagnon T. J. Am. Chem. Soc. 2004, 126: 5192

<A NAME="RT14309SS-17">17</A> Braun JV. Kühn M. Weismantel J. Leibigs Ann. Chem. 1926, 449: 249

<A NAME="RT14309SS-18">18</A> Incarvito C. Lam M. Rhatigan B. Rheingold AL. Qin CJ. Gavrilova AL. Bosnich B. J. Chem. Soc., Dalton Trans. 2001, 3478

<A NAME="RT14309SS-19">19</A> Eggert H. Djerassi C. J. Am. Chem. Soc. 1973, 95: 3710

<A NAME="RT14309SS-20">20</A> Closson RD. Napolitano JP. Ecke GG. Kolka AJ. J. Org. Chem. 1957, 22: 646

<A NAME="RT14309SS-21">21</A> Miller RE. J. Org. Chem. 1960, 25: 2126