Abstract
This personal account summarizes our recent developments of catalytic hydrosilylations and hydrogenations of carboxylic amides and nitriles to selectively give amines. Special focus is given to highly chemoselective iron- and zinc-catalyzed reductions of amides.
Similar content being viewed by others
References
Ricci A (2000) Modern amination methods. New York, Wiley
Brunet JJ, Chu NC, Rodriguez-Zubiri M (2007) Eur J Inorg Chem 30:4711
Lee AV, Schafer LL (2007) Eur J Inorg Chem 16:2243
Severin R, Doye S (2007) Chem Soc Rev 36:1407
Hultzsch KC, Gribkov DV, Hampel F (2005) J Organomet Chem 690:4441
Odom AL (2005) Dalton Trans 225
Hartwig JF (2004) Pure Appl Chem 76:507
Doye S (2004) Synlett 10:1653
Seayad J, Tillack A, Hartung CG, Beller M (2002) Adv Synth Catal 344:795
Beller M, Breindl C, Eichberger M, Hartung CG, Seayad J, Thiel O, Tillack A, Trauthwein H (2002) Synlett 10:1579
Krüger K, Tillack A, Beller M (2009) ChemSusChem 2:715–719
Seyden-Penne J (1997) Reductions by the alumino and borohydrides in organic synthesis, 2nd edn. Wiley, New York
Andersson PG, Munslow IJ (2008) Modern reduction methods. Wiley, New York
Rylander PN (1979) Catalytic hydrogenation in organic syntheses. Academic Press, New York
Magro AAN, Eastham GR, Cole-Hamilton DJ (2007) Chem Commun 3154–3156
Beller M, Eichberger M, Trauthwein H (1997) Angew Chem Int Ed Engl 36:2225–2227
Beller M, Breindl C, Riermeier TH, Eichberger M, Trauthwein H (1998) Angew Chem Int Ed Engl 37:3389–3391
Beller M, Trauthwein H, Eichberger M, Breindl C, Herwig J, Müller TE, Thiel OR (1999) Chem Eur J 5:1306–1319
Tillack A, Garcia Castro I, Hartung CG, Beller M (2002) Angew Chem Int Ed Engl 41:2541–2543
Tillack A, Jiao H, Garcia Castro I, Hartung CG, Beller M (2004) Chem Eur J 10:2409–2420
Khedkar V, Tillack A, Michalik M, Beller M (2004) Tetrahedron Lett 45:3123–3126
Alex K, Tillack A, Schwarz N, Beller M (2008) Angew Chem Int Ed Engl 47:2314–2317
Alex K, Tillack A, Schwarz N, Beller M (2008) ChemSusChem 1:333–338
Zimmermann B, Herwig J, Beller M (1999) Angew Chem Int Ed Engl 38:2372–2375
Seayad A, Ahmed M, Klein H, Jackstell R, Gross T, Beller M (2002) Science 297:1676–1678
Moballigh A, Seayad A, Jackstell R, Beller M (2003) J Am Chem Soc 125:10311–10318
Moballigh A, Seayad AM, Jackstell R, Beller M (2003) Angew Chem Int Ed Engl 42:5615–5619
Routaboul L, Buch C, Klein H, Jackstell R, Beller M (2005) Tetrahedron Lett 46:7401–7405
Bronger RPJ, Kamer PCJ, van Leeuwen PWNM, Ahmed M, Seayad AM, Jackstell R, Beller M (2006) Chem Eur J 12:8979–8988
Ahmed M, Buch C, Routaboul L, Jackstell R, Klein H, Spannenberg A, Beller M (2007) Chem Eur J 13:1594–1601
Tillack A, Hollmann D, Michalik D, Beller M (2006) Tetrahedron Lett 47:8881–8885
Hollmann D, Tillack A, Michalik D, Jackstell R, Beller M (2007) Chem Asian J 2:403–410
Hollmann D, Bähn S, Tillack A, Beller M (2007) Angew Chem Int Ed Engl 46:8291–8294
Hollmann D, Bähn S, Tillack A, Beller M (2008) Chem Commun 3199–3201
Bähn S, Hollmann D, Tillack A, Beller M (2008) Adv Synth Catal 350:2099–2103
Hollmann D, Bähn S, Tillack A, Parton R, Altink R, Beller M (2008) Tetrahedron Lett 49:5742–5745
Tillack A, Hollmann D, Mevius K, Michalik D, Bähn S, Beller M (2008) Eur J Org Chem 28:4745–4750
Bähn S, Tillack A, Imm S, Mevius K, Michalik D, Hollmann D, Neubert L, Beller M (2009) ChemSusChem 2:551–557
Suarez T, Fontal B (1988) J Mol Catal 45:335–344
Joshi AM, MacFarlane KS, James BR, Frediani P (1992) In: Smith KJ, Sanford EC (eds) Progress in catalysis, vol 73. Elsevier, New York, pp 143–146
Joshi AM, MacFarlane KS, James BR, Frediani P (1992) Catalysis of organic reactions. Chemical industries 53. Dekker, New York, pp 497–502
Frontal B, Reyes M, Suárez T, Bellandi F, Ruiz N (1999) J Mol Catal A 149:87–97
Bianchini C, Dal Santo V, Meli A, Oberhauser W, Psaro R, Vizza F (2000) Organometallics 19:2433–2444
Li T, Bergner I, Haque FN, Zimmer-De Iuliis M, Song D, Morris R (2007) Organometallics 26:5940–5949
Yoshida T, Okano T, Otsuka S (1979) J Chem Soc Chem Commun 19:870–871
Xie X, Liotta CL, Eckert CA (2004) Ind Eng Chem Res 43:7908–7911
Chin CS, Lee B (1992) Catal Lett 14:135–140
Grey RA, Pez GP, Wallo A (1981) J Am Chem Soc 103:7536–7545
Mukherjee DK, Palit BK, Saha CR (1994) J Mol Catal 88:57–70
Takemoto S, Kawamura H, Yamada Y, Okada T, Ono A, Yoshikawa E, Mizobe Y, Hidai M (2002) Organometallics 21:3897–3904
Kukula P, Studer M, Blaser H-U (2004) Adv Synth Catal 346:1487–1493
Enthaler S, Junge K, Addis D, Erre G, Beller M (2008) ChemSusChem 1:1006–1010
Enthaler S, Addis D, Junge K, Erre G, Beller M (2008) Chem Eur J 14:9491–9494
Addis D, Enthaler S, Junge K, Wendt B, Beller M (2009) Tetrahedron Lett 50:3654–3656
Ohta T, Kamiya M, Nobutomo M, Kusui K, Furukawa I (2005) Bull Chem Soc Jpn 78:1856–1861
Kuwano R, Takahashi M, Ito Y (1998) Tetrahedron Lett 39:1017–1020
Igarashi M, Fuchikami T (2001) Tetrahedron Lett 42:1945–1947
Motoyama H, Mitsui K, Ishida T, Nagashima H (2005) J Am Chem Soc 127:13150–13151
Hanada S, Ishida T, Motoyama Y, Nagashima H (2007) J Org Chem 72:7551–7559
Matsubara K, Iura T, Maki T, Nagashima H (2002) J Org Chem 67:4985–4988
Sasakuma H, Motoyama Y, Nagashima H (2007) Chem Commun 4916–4918
Hanada S, Motoyama Y, Nagashima H (2006) Tetrahedron Lett 47:6173–6177
Fernandes AC, Romão CC (2007) J Mol Catal 272:60–63
Sakai N, Fuhji K, Konakahara T (2008) Tetrahedron Lett 49:6873–6875
Selvakumar K, Harrod JF (2001) Angew Chem Int Ed Engl 40:2129–2131
Plietker B (ed) (2008) Iron catalysis in organic chemistry. Wiley-VCH, Weinheim
Enthaler S, Junge K, Beller M (2008) Angew Chem Int Ed Engl 47:3317
Gaillard S, Renaud J-L (2008) ChemSusChem 1:505
Bolm C, Legros J, Paith JL, Zani L (2004) Chem Rev 104:6217
Correa A, Mancheño OG, Bolm C (2008) Chem Soc Rev 37:1108
Sherry BD, Fürstner A (2008) Acc Chem Res 41:1500
Fürstner A (2009) Angew Chem Int Ed Engl 48:1364
Bullock RM (2007) Angew Chem Int Ed Engl 46:7360
Enthaler S, Hagemann B, Erre G, Junge K, Beller M (2006) Chem Asian J 1:598–604
Enthaler S, Erre G, Tse MK, Junge K, Beller M (2006) Tetrahedron Lett 47:8095–8099
Shaikh N, Junge K, Beller M (2007) Org Lett 9:5429–5432
Enthaler S, Spilker B, Erre G, Junge K, Beller M (2008) Tetrahedron 63:3867–3876
Shaikh NS, Enthaler S, Junge K, Beller M (2008) Angew Chem Int Ed Engl 47:2497–2501
Junge K, Wendt B, Shaikh N, Beller M (2010) Chem Commun 1769–1771
Addis D, Shaikh N, Zhou S, Das S, Junge K, Beller M (2010) Chem Asian J. doi:10.1002/asia.201000064
Zhou S, Addis D, Das S, Junge K, Beller M (2009) Chem Commun 4883–4885
Zhou S, Junge K, Addis D, Das S, Beller M (2009) Org Lett 11:2461–2464
Zhou S, Junge K, Addis D, Das S, Beller M (2009) Angew Chem Int Ed Engl 48:9507–9510
Das S, Addis D, Zhou S, Junge K, Beller M (2010) J Am Chem Soc 132:1770–1771
Buchwald SL (1993) Chem Eng News 71:2
Saudan LA, Saudan CM, Debieux C, Wyss P (2007) Angew Chem Int Ed Engl 46:7473–7476
Kuriyama W, Ino Y, Ogata O, Sayo N, Saito T (2009) Adv Synth Catal 352:92–96
Zhang J, Leitus G, Ben-David Y, Milstein D (2006) Angew Chem Int Ed Engl 45:1113–1115
Aoun R, Renaud J-L, Dixneuf PH, Bruneau C (2005) Angew Chem Int Ed Engl 44:2021–2023
Ito M, Sakaguchi A, Kobayashi C, Ikariya T (2007) J Am Chem Soc 129:290–291
Acknowledgements
This work has been funded by the State of Mecklenburg-Western Pomerania, the BMBF, the DFG (Leibniz-price). We thank Dr. W. Baumann, Dr. C. Fischer, S. Buchholz, S. Schareina, A. Kammer, A. Koch, S. Rossmeisl, and K. Mevius (all at the LIKAT) for their excellent technical and analytical support.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Das, S., Zhou, S., Addis, D. et al. Selective Catalytic Reductions of Amides and Nitriles to Amines. Top Catal 53, 979–984 (2010). https://doi.org/10.1007/s11244-010-9526-4
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11244-010-9526-4