Overview over synthetic reduction methods
1) Reduction of C-C-Bonds
2) Reduction of C-O Bonds
3) Reduction of C-N Bonds
4) Reductive functional group conversion
5) Reduction of other functional groups, e.g. nitro groups, sulphur containing groups, ...
6) Various
1) Reduction of C-C-Bondsreduction of C=C bond in nitrostyrenesZinc borohydride:
Post 510437
(Rhodium: "Nitroalkene Reduction with Zinc Borohydride", Novel Discourse)MeOH/NaBH
4:
Post 510662
(Rhodium: "Varma & Kabalka: Nitroalkene -BH4-> Nitroalkane", Novel Discourse)Borohydride Exchange Resin:
Post 510662
(Rhodium: "Varma & Kabalka: Nitroalkene -BH4-> Nitroalkane", Novel Discourse)HCOOH/triethylamine:
Post 444306
(Lego: "Formic acid and triethylamine", Novel Discourse)Hantzsch ester/silical gel:
Post 500814
(azole: "reduction with Hantzsch ester/SiO2 (full article)", Novel Discourse)NaBH
4/PTC:
Post 426052
(Barium: "Novel high-yielding C=C reduction of nitrostyrenes", Novel Discourse) RhCl
3/H
2/PTC:
Post 398684
(Barium: "C=C bond hydrogenation of beta-nitrostyrene", Novel Discourse)benzaldehyde/o-phenylenediamine:
Post 352950
(Barium: "Get that double bond without borohydride", Novel Discourse),
Post 352950
(Barium: "Get that double bond without borohydride", Novel Discourse)general C=C reduction methodsPdCl
2/H
2:
Post 470158 (missing)
(azole: "reductions with NaAlH4 in hydrocarbon media", Russian HyperLab)2) Reduction of C-O BondsReduction of carboxylic acids & esters to aldehydesSodium bis-(2-methoxy-ethoxy) aluminium hydride/saccharine:
Post 405255
(GC_MS: "acid > aldehyde", Novel Discourse)PdCl
2/H
2/N-ethylmorpholine/2-chloro-4,6-dimethoxy[1,3,5]triazine:
Post 430441
(Lego: "Reduction of carboxylic acids to aldehydes", Novel Discourse)NaH
2PO
2/Pd(OAc)
2/tricyclohexylphospine/pivalic anhydride:
Post 304273
(karel: "Aldehydes from carboxylic acids", Serious Chemistry)Reduction of carboxylic acids & esters to alcoholsZinc borohydride:
Post 485626
(Lego: "Zn(BH4)2/Pyridine also reduces COOH, Pt. 1", Novel Discourse)NaAlH
4:
Post 470158 (missing)
(azole: "reductions with NaAlH4 in hydrocarbon media", Russian HyperLab)LiBH
4:
Post 413088
(Rhodium: "Reduction of esters to alcohols w/ in situ LiBH4", Novel Discourse) Reduction of carboxylic acids & esters to hydrocarbonsLiAlH
4/AlCl:
3 Post 476162
(Rhodium: "A One-Step Ester to Hydrocarbon Reduction", Novel Discourse)Triethylsilane/B(C
6F
5)
3:
Post 194986
(Rhodium: "First published direct reduction of COOH to CH3", Serious Chemistry)Reduction of carboxylic acid chlorides to aldehydesNa
4/pyridine:
Post 509148
(Rhodium: "NaBH4:Pyridine: Acid Chlorides to Aldehydes", Chemistry Discourse)Na
4/PCC:
Post 491806 (missing)
(Vitus_Verdegast: "benzoylchloride -> benzaldehyde w NaBH4/PCC", Chemistry Discourse)HCOOH:
Post 464426 (missing)
(Lilienthal: "acid chlorides to aldehydes with formic acid", Tryptamine Chemistry)Reduction of carboxylic acid chlorides to alcoholsReduction of carboxylic acid chlorides to hydrocarbonsReduction of aldehydes & acetals to alcoholsZinc borohydride:
Post 435043
(Rhodium: "Zn(BH4)2/Pyridine reduces carbonyl compounds", Novel Discourse)Reduction of aldehydes & acetals to hydrocarbonsCTH/NH
4HCOO:
Post 507520
(Rhodium: "CTH reduction of various functional groups", Novel Discourse) Reduction of alcohols to hydrocarbonsHI/RP:
Post 511694
(Rhodium: "HI/RP reduction of aminoalcohols", Stimulants)Me
3SiCl-NaI-CH
3CN:
Post 507401
(Rhodium: "Me3SiCl-NaI-MeCN: Benzylic Alcohol Deoxygenation", Novel Discourse) 3) Reduction of C-N BondsReduction of imines to aminesPMHS:
Post 505083
(Lego: "Asymetric reduction of imines with PMHS", Chemistry Discourse)Reduction of enamines to aminesReduction of nitriles to aminesBu
4BH
4:
Post 507503 (missing)
(Rhodium: "Nitriles and Amides to Amines with n-Bu4BH4", Novel Discourse)CoCl
2/NaBH
4:
Post 507524
(Rhodium: "Reduction of Nitrile/Nitro/Amide to Primary Amines", Novel Discourse)Reduction of amides to aminesBu
4BH
4:
Post 507503 (missing)
(Rhodium: "Nitriles and Amides to Amines with n-Bu4BH4", Novel Discourse)CoCl
2/NaBH
4:
Post 507524
(Rhodium: "Reduction of Nitrile/Nitro/Amide to Primary Amines", Novel Discourse)Thioamides to aminesPost 470674
(Lego: "Reduction of secondary thioamide with Zn/HCl", Serious Chemistry)4) Reductive functional group conversionReductive amination - ketone/aldehyde to amineZinc borohydride:
Post 481426
(dioulasso: "N-methylation of amines with Zn(BH4)2", Novel Discourse)Titanium(IV)isopropoxide/NaBH
4:
Post 364157
(Rhodium: "Titanium(IV)isopropoxide reductive amination", Novel Discourse),
Post 485344 (missing)
(Lego: "Reductive amination with Ti(iPrO)4/NaBH4", Novel Discourse)Zn/iPrOH/mol sieves:
Post 413690
(Lego: "Red. amination with Zn/iPrOH and mol. sieves", Novel Discourse)NaBH(OAc)
3:
Post 503100
(Rhodium: "NaBH(OAc)3 in Reductive Amination", Novel Discourse)Cl
3SiH/DMF:
Post 458268
(Rhodium: "Trichlorosilane-DMF for Reductive Amination", Novel Discourse)Alcohol to amine (no real reduction)Nitroalkenes to ketone/aldehydeChromium chloride:
Post 512099
(Rhodium: "Varma&Kabalka: Cr(II) Nitrostyrene Reduction", Novel Discourse)5) Reduction of other functional groups, e.g. nitro groups, sulphur containing groups, ...Nitro to amineZn/ammonium formate:
Post 351892
(foxy2: "Reduction of nitro groups w. Zinc/Ammonium formate", Chemistry Discourse)Zinc borohydride:
Post 435007 (missing)
(Lego: "Zn(BH4)2/Pyridine reduces nitro compounds", Novel Discourse)Mg/Hydrazinium Monoformate:
Post 512087
(Rhodium: "Nitro -> Amine with Mg/Hydrazinium Monoformate", Novel Discourse)Titan(II):
Post 474130 (missing)
(Lego: "Selective reduction of nitro compounds with Ti(II)", Novel Discourse) NaBH
4/NiCl
2: 505481
CHT/NH
4HCOO:
Post 507520
(Rhodium: "CTH reduction of various functional groups", Novel Discourse)Sn complex:
Post 508071
(Rhodium: "Reduction of Nitro/Azide groups with Sn complex", Chemistry Discourse)CoCl
2/NaBH
4:
Post 507524
(Rhodium: "Reduction of Nitrile/Nitro/Amide to Primary Amines", Novel Discourse)Azides to aminesZn/NH
4Cl:
Post 399263
(endo1: "The reduction of azides to amines w zinc/amoniumCl", Novel Discourse)Nitroalkenes to aldoximes/ketoximesCoCl
2:
Post 512099
(Rhodium: "Varma&Kabalka: Cr(II) Nitrostyrene Reduction", Novel Discourse)SnCl
2:
Post 507809
(Rhodium: "Varma & Kabalka: SnCl2 Nitroalkene -> Oxime", Methods Discourse)CTH/NaH
2PO
2:
Post 509830
(Rhodium: "Hypophosphite CTH: Nitroalkenes to Oximes", Novel Discourse)Nitroalkenes to aminoalkanesBH
3·THF:
Post 511296
(Rhodium: "Nitroalkenes to Amines w/ BH3·THF made in situ", Methods Discourse)LiAlH
4:
Post 506993
(Rhodium: "Mescaline, Amphetamine etc. by LAH reduction", Novel Discourse)Oximes to aminesMg/NH
4HCOO:
Post 498659 (missing)
(demorol: "Reduction of Oximes using Mg/Ammonium Formate", Novel Discourse)Zn/NH
3:
Post 413177
(Lego: "Reduction of ketoximes with Zn/NH3", Novel Discourse)Sulphonic acids to thiols/thiophenols6) VariousReviewsNitroalkenes:
Post 510333
(Rhodium: "Nitroalkene Synthesis & Reduction Review", Novel Discourse),
Post 509994
(Rhodium: "Varma & Kabalka: Nitroalkene Reduction Review", Novel Discourse) Hydrides:
Post 502900
(Rhodium: "Comprehensive Hydride Reduction Review", Novel Discourse)Clemmens reduction:
Post 508503
(Rhodium: "Organic Reactions: The Clemmensen Reduction", Novel Discourse)Wolff-Kishner Reduction:
Post 508584
(Rhodium: "Organic Reactions: The Wolff-Kishner Reduction", Novel Discourse) Removal of protecing groupsMg/hydrazinium monoformate:
Post 499259
(Rhodium: "Great, Demorol!", Novel Discourse)
