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    Digest: Reduction methods in organic synthesis   Please login to post  

 
    Lego
(Hive Bee)
11-09-04 20:39
No 512224
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      Reduction methods in organic synthesis
(Rated as: excellent)
    

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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