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Chemistry Discourse | Thread: Previous Forum index Next | |
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Digest: Reduction methods in organic synthesis | Please login to post | |
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Lego (Hive Bee) 11-09-04 20:39 No 512224 
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Reduction methods in organic synthesis (Rated as: excellent) |
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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-Bonds reduction of C=C bond in nitrostyrenes Zinc borohydride: Post 510437 (Rhodium: "Nitroalkene Reduction with Zinc Borohydride", Novel Discourse) MeOH/NaBH4: 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) NaBH4/PTC: Post 426052 (Barium: "Novel high-yielding C=C reduction of nitrostyrenes", Novel Discourse) RhCl3/H2/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 methods PdCl2/H2: Post 470158 (azole: "reductions with NaAlH4 in hydrocarbon media", Russian HyperLab) 2) Reduction of C-O Bonds Reduction of carboxylic acids & esters to aldehydes Sodium bis-(2-methoxy-ethoxy) aluminium hydride/saccharine: Post 405255 (GC_MS: "acid > aldehyde", Novel Discourse) PdCl2/H2/N-ethylmorpholine/2-chloro-4,6-dimethoxy[1,3,5]triazine: Post 430441 (Lego: "Reduction of carboxylic acids to aldehydes", Novel Discourse) NaH2PO2/Pd(OAc)2/tricyclohexylphospine/pivalic anhydride: Post 304273 (karel: "Aldehydes from carboxylic acids", Serious Chemistry) Reduction of carboxylic acids & esters to alcohols Zinc borohydride: Post 485626 (Lego: "Zn(BH4)2/Pyridine also reduces COOH, Pt. 1", Novel Discourse) NaAlH4: Post 470158 (azole: "reductions with NaAlH4 in hydrocarbon media", Russian HyperLab) LiBH4: Post 413088 (Rhodium: "Reduction of esters to alcohols w/ in situ LiBH4", Novel Discourse) Reduction of carboxylic acids & esters to hydrocarbons LiAlH4/AlCl:3 Post 476162 (Rhodium: "A One-Step Ester to Hydrocarbon Reduction", Novel Discourse) Triethylsilane/B(C6F5)3: Post 194986 (Rhodium: "First published direct reduction of COOH to CH3", Serious Chemistry) Reduction of carboxylic acid chlorides to aldehydes Na4/pyridine: Post 509148 (Rhodium: "NaBH4:Pyridine: Acid Chlorides to Aldehydes", Chemistry Discourse) Na4/PCC: Post 491806 (Vitus_Verdegast: "benzoylchloride -> benzaldehyde w NaBH4/PCC", Chemistry Discourse) HCOOH: Post 464426 (Lilienthal: "acid chlorides to aldehydes with formic acid", Tryptamine Chemistry) Reduction of carboxylic acid chlorides to alcohols Reduction of carboxylic acid chlorides to hydrocarbons Reduction of aldehydes & acetals to alcohols Zinc borohydride: Post 435043 (Rhodium: "Zn(BH4)2/Pyridine reduces carbonyl compounds", Novel Discourse) Reduction of aldehydes & acetals to hydrocarbons CTH/NH4HCOO: Post 507520 (Rhodium: "CTH reduction of various functional groups", Novel Discourse) PMHS-B(C6F5)3:Post 529706 (Rhodium: "Carbonyl Group to Methylene with PMHS-B(C6F5)3", Chemistry Discourse) Reduction of alcohols to hydrocarbons HI/RP: Post 511694 (Rhodium: "HI/RP reduction of aminoalcohols", Stimulants) Me3SiCl-NaI-CH3CN: Post 507401 (Rhodium: "Me3SiCl-NaI-MeCN: Benzylic Alcohol Deoxygenation", Novel Discourse) 3) Reduction of C-N Bonds Reduction of imines to amines PMHS: Post 505083 (Lego: "Asymetric reduction of imines with PMHS", Chemistry Discourse) Reduction of enamines to amines Reduction of nitriles to amines Bu4BH4: Post 507503 (Rhodium: "Nitriles and Amides to Amines with n-Bu4BH4", Novel Discourse) CoCl2/NaBH4: Post 507524 (Rhodium: "Reduction of Nitrile/Nitro/Amide to Primary Amines", Novel Discourse) Reduction of amides to amines Bu4BH4: Post 507503 (Rhodium: "Nitriles and Amides to Amines with n-Bu4BH4", Novel Discourse) CoCl2/NaBH4: Post 507524 (Rhodium: "Reduction of Nitrile/Nitro/Amide to Primary Amines", Novel Discourse) Thioamides to amines Post 470674 (Lego: "Reduction of secondary thioamide with Zn/HCl", Serious Chemistry) 4) Reductive functional group conversion Reductive amination - ketone/aldehyde to amine Zinc borohydride: Post 481426 (dioulasso: "N-methylation of amines with Zn(BH4)2", Novel Discourse) Titanium(IV)isopropoxide/NaBH4: Post 364157 (Rhodium: "Titanium(IV)isopropoxide reductive amination", Novel Discourse), Post 485344 (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) Cl3SiH/DMF: Post 458268 (Rhodium: "Trichlorosilane-DMF for Reductive Amination", Novel Discourse) Alcohol to amine (no real reduction) Nitroalkenes to ketone/aldehyde Chromium 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 amine Zn/ammonium formate: Post 351892 (foxy2: "Reduction of nitro groups w. Zinc/Ammonium formate", Chemistry Discourse) Zinc borohydride: Post 435007 (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 (Lego: "Selective reduction of nitro compounds with Ti(II)", Novel Discourse) NaBH4/NiCl2: 505481 CHT/NH4HCOO: 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) CoCl2/NaBH4: Post 507524 (Rhodium: "Reduction of Nitrile/Nitro/Amide to Primary Amines", Novel Discourse) Azides to amines Zn/NH4Cl: Post 399263 (endo1: "The reduction of azides to amines w zinc/amoniumCl", Novel Discourse) Nitroalkenes to aldoximes/ketoximes CoCl2: Post 512099 (Rhodium: "Varma&Kabalka: Cr(II) Nitrostyrene Reduction", Novel Discourse) SnCl2: Post 507809 (Rhodium: "Varma & Kabalka: SnCl2 Nitroalkene -> Oxime", Methods Discourse) CTH/NaH2PO2: Post 509830 (Rhodium: "Hypophosphite CTH: Nitroalkenes to Oximes", Novel Discourse) Nitroalkenes to aminoalkanes BH3·THF: Post 511296 (Rhodium: "Nitroalkenes to Amines w/ BH3·THF made in situ", Methods Discourse) LiAlH4: Post 506993 (Rhodium: "Mescaline, Amphetamine etc. by LAH reduction", Novel Discourse) Oximes to amines Mg/NH4HCOO: Post 498659 (demorol: "Reduction of Oximes using Mg/Ammonium Formate", Novel Discourse) Zn/NH3: Post 413177 (Lego: "Reduction of ketoximes with Zn/NH3", Novel Discourse) Sulphonic acids to thiols/thiophenols 6) Various Reviews Nitroalkenes: 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 groups Mg/hydrazinium monoformate: Post 499259 (Rhodium: "Great, Demorol!", Novel Discourse) The tendency is to push it as far as you can |
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