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Amide reduction

From Wikipedia, the free encyclopedia
Organic reaction where amide is converted to Amine or Aldehyde

Amide reduction is a reaction inorganic synthesis where anamide isreduced to either anamine or analdehydefunctional group.[1][2]

Catalytic hydrogenation

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Catalytichydrogenation can be used to reduce amides toamines; however, the process often requires high hydrogenation pressures and reaction temperatures to be effective (i.e. often requiring pressures above 197atm and temperatures exceeding 200 °C).[1]Selective catalysts for the reaction includecopper chromite,rhenium trioxide andrhenium(VII) oxide or bimetallic catalyst.[3][4][5]

Amines from other hydride sources

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Reducing agents able to effect this reaction includemetal hydrides such aslithium aluminium hydride,[6][7][8][9][10] orlithium borohydride in mixed solvents oftetrahydrofuran andmethanol.[11]

Reduction of amides to amines

Iron catalysis bytriiron dodecacarbonyl in combination withpolymethylhydrosiloxane has been reported.[12]

Lawesson's reagent converts amides tothioamides, which then catalytically desulfurize.[13]

Noncatalytic routes to aldehydes

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Some amides can be reduced to aldehydes in theSonn-Müller method, but most routes to aldehydes involve a well-chosen organometallic reductant.

Lithium aluminum hydride reduces an excess of N,N-disubstituted amides to an aldehyde:[citation needed]

R(CO)NRR' + LiAlH4 → RCHO + HNRR'

With further reduction thealcohol is obtained.

Schwartz's reagent reduces amides to aldehydes,[14] and so doeshydrosilylation with a suitable catalyst.

References

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  1. ^abNishimura, Shigeo (2001).Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis (1st ed.). New York: Wiley-Interscience. pp. 406–411.ISBN 978-0-471-39698-7.
  2. ^March, Jerry (1985).Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (3rd ed.). New York: Wiley.ISBN 9780471854722.OCLC 642506595.
  3. ^Mitsudome, Takato; Miyagawa, Kazuya; Maeno, Zen; Mizugaki, Tomoo; Jitsukawa, Koichiro; Yamasaki, Jun; Kitagawa, Yasutaka; Kaneda, Kiyotomi (2017-08-01)."Mild Hydrogenation of Amides to Amines over a Platinum-Vanadium Bimetallic Catalyst".Angewandte Chemie International Edition.56 (32):9381–9385.doi:10.1002/anie.201704199.PMID 28649715.
  4. ^Zhang, Yue; Zhang, Fan; Li, Lin; Liu, Fei; Wang, Aiqin (2022-10-07)."Highly Chemoselective Reduction of Amides to Amines over a Ruthenium‐Molybdenum Bimetallic Catalyst".ChemistrySelect.7 (37).doi:10.1002/slct.202203030.ISSN 2365-6549.S2CID 252725710.
  5. ^Pennetier, Alex; Hernandez, Willinton Y.; Kusema, Bright T.; Streiff, Stéphane (2021-08-25)."Efficient hydrogenation of aliphatic amides to amines over vanadium-modified rhodium supported catalyst".Applied Catalysis A: General.624 118301.doi:10.1016/j.apcata.2021.118301.ISSN 0926-860X.S2CID 238850541.
  6. ^Cope, Arthur C.; Ciganek, Engelbert (1959). "N,N-Dimethylcyclohexylmethylamine".Organic Syntheses.39: 19.doi:10.15227/orgsyn.039.0019.
  7. ^Wilson, C. V.; Stenberg, J. F. (1956). "Laurylmethylamine".Organic Syntheses.36: 48.doi:10.15227/orgsyn.036.0048.
  8. ^Moffett, Robert Bruce (1953). "2,2-Dimethylpyrrolidine".Organic Syntheses.33: 32.doi:10.15227/orgsyn.033.0032.
  9. ^Park, Chung Ho; Simmons, Howard E. (1974). "Macrocyclic Diimines: 1,10-Diazacylooctadecane".Organic Syntheses.54: 88.doi:10.15227/orgsyn.054.0088.
  10. ^Seebach, Dieter; Kalinowski, Hans-Otto; Langer, Werner; Crass, Gerhard; Wilka, Eva-Maria (1983). "Chiral Media for Asymmetric Solvent Inductions".Organic Syntheses.61: 24.doi:10.15227/orgsyn.061.0024.
  11. ^Ookawa, Atsuhiro; Soai, Kenso (1986). "Mixed solvents containing methanol as useful reaction media for unique chemoselective reductions within lithium borohydride".The Journal of Organic Chemistry.51 (21):4000–4005.doi:10.1021/jo00371a017.
  12. ^Zhou, S.; Junge, K.; Addis, D.; Das, S.; Beller, M. (2009). "A Convenient and General Iron-Catalyzed Reduction of Amides to Amines".Angewandte Chemie International Edition in English.48 (50):9507–9510.doi:10.1002/anie.200904677.PMID 19784999.
  13. ^Taber, Douglass F (5 June 2006)."The Boger Route to (-)-Vindoline".Org. Chem. Highlights. Discussion of (12)→(13).
  14. ^Leighty, M. W.; Spletstoser, J. T.; Georg, Gunda I. (2011)."Mild Conversion of Tertiary Amides to Aldehydes Using Cp2ZrHCl (Schwartz's Reagent)".Org. Synth.88:427–437.doi:10.1002/0471264229.os088.39.ISBN 978-0-471-26422-4.

External links

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