Mild and Convenient Method for Reduction of Carbonyl Compounds with the NaBH4/Charcoal System in Wet THF

2006 ◽  
Vol 61 (10) ◽  
pp. 1275-1281 ◽  
Author(s):  
Davood Setamdideh ◽  
Behzad Zeynizadeh
Keyword(s):  
Convenient Method ◽  
Carbonyl Compounds ◽  
Aprotic Solvent ◽  
Reduction Reactions ◽  
Unsaturated Aldehydes ◽  
Aldehydes And Ketones

The NaBH4/C (charcoal) system reduces a variety of carbonyl compounds such as aldehydes, ketones, acyloins and α-diketones to their corresponding alcohols in high to excellent yields. Reduction reactions were carried out in wet THF at r. t. In addition, regioselective 1,2-reduction of α,β - unsaturated aldehydes and ketones was achieved perfectly with this reducing system. By decreasing the amount of aprotic solvent, all reductions took place fast and efficiently under solid-gel condition

NaBH4/NaHSO4·H2O a Heterogeneous Acidic System for a Mild and Convenient Reduction of Carbonyl Compounds under Protic Condition

2005 ◽  
Vol 60 (4) ◽  
pp. 453-457 ◽  
Author(s):  
Behzad Zeynizadeh ◽  
Tarifeh Behyar
Keyword(s):  
Carbonyl Compounds ◽  
Room Temperature ◽  
Reduction Reactions ◽  
Heterogeneous Condition ◽  
Unsaturated Aldehydes ◽  
Sodium Bisulfate ◽  
Aldehydes And Ketones ◽  
Acidic Reagent

NaBH4 in the presence of sodium bisulfate (NaHSO4·H2O), a weakly acidic reagent, efficiently reduces a variety of carbonyl compounds such as aldehydes, ketones, α,β -unsaturated aldehydes and ketones, α-diketones and acyloins to their corresponding alcohols in acetonitrile under heterogeneous condition. Reduction reactions were accomplished at room temperature or under reflux condition

Decarboxylative Umpolung Synthesis of Amines from Carbonyl Compounds

Synlett ◽  
2020 ◽  
Vol 31 (16) ◽  
pp. 1543-1550
Author(s):  
Baoguo Zhao ◽  
Wen-Wen Chen
Keyword(s):  
Carbonyl Compounds ◽  
Aromatic Aldehydes ◽  
High Reactivity ◽  
Mild Conditions ◽  
Intramolecular Reaction ◽  
Unsaturated Aldehydes ◽  
Recent Advances ◽  
Intermolecular Reaction ◽  
Aldehydes And Ketones

2-Azaallyl anions are valuable intermediates which have versatile applications in functionalization with various electrophiles. Decarboxylation of the imines formed from aromatic aldehydes and α,α-diphenylglycine provides an interesting and efficient way to generate delocalized 2-azaallyl anions, which display high reactivity toward different electrophiles with excellent regioselectivity at the diphenylketimino aryl carbon of the 2-azaallyl anions. The transformation produces various amines in good yields under very mild conditions. This Synpacts article highlights the recent advances on the decarboxylative umpolung synthesis of amines from carbonyl compounds.1 Introduction2 Decarboxylative Umpolung Reactions of Carbonyl Compounds with Different Electrophiles2.1 Reaction with π-Allyl–Pd(II) Species2.2 Reaction with Morita–Baylis–Hillman Adducts2.3 Reaction with Imines2.3.1 Intermolecular Reaction with N-Ts Imines2.3.2 Intramolecular Reaction with Chiral N-tert-Butanesulfinyl Imines2.4 Reaction with Aldehydes and Ketones3 Decarboxylative Umpolung Reaction of α,β-Unsaturated Aldehydes with Aldehydes4 Conclusion

scholarly journals Reduction of carbonyl compounds via hydrosilylation catalyzed by well-defined PNP-Mn(I) hydride complexes

2021 ◽  
Author(s):  
Stefan Weber ◽  
Dina Iebed ◽  
Mathias Glatz ◽  
Karl Kirchner
Keyword(s):  
Carbonyl Compounds ◽  
Hydrogen Donor ◽  
Synthetic Chemistry ◽  
Double Bonds ◽  
Reduction Reactions ◽  
Hydride Complexes ◽  
Unsaturated Compounds ◽  
Aldehydes And Ketones ◽  
Hydrogenation Reactions

AbstractReduction reactions of unsaturated compounds are fundamental transformations in synthetic chemistry. In this context, the reduction of polarized double bonds such as carbonyl or C=C motifs can be achieved by hydrogenation reactions. We describe here a highly chemoselective Mn(I)-based PNP pincer catalyst for the hydrosilylation of aldehydes and ketones employing polymethylhydrosiloxane (PMHS) as inexpensive hydrogen donor. Graphic abstract

New Zinc Catalyst for Hydrosilylation of Carbonyl Compounds

Synthesis ◽  
2019 ◽  
Vol 51 (17) ◽  
pp. 3305-3312 ◽  
Author(s):  
Iryna D. Alshakova ◽  
Georgii I. Nikonov
Keyword(s):  
Carbonyl Compounds ◽  
Zinc Complex ◽  
Allylic Alcohols ◽  
Reaction Conditions ◽  
Unsaturated Aldehydes ◽  
Substoichiometric Amount ◽  
Aldehydes And Ketones ◽  
Catalytic Hydrosilylation ◽  
Catalyst Load

A new zinc complex was synthesized and applied in the catalytic hydrosilylation of carbonyl compounds. Optimization of the reaction conditions showed that the presence a substoichiometric amount of methanol accelerates the process significantly. The reaction can proceed at very low catalyst load (down to 0.1 mol%) under mild reaction conditions. The reaction tolerates the presence of C=C bonds, and thus can be useful for the synthesis of allylic alcohols from α,β-unsaturated aldehydes and ketones.

Überraschende Selektivitäten bei der Cycloaddition von a ,ß - ungesättigten Aldehyden und Ketonen an trifluormethyl-substituierte Hetero-1.3 -diene / Unexpected Selectivity Phenomena in Cycloaddition Reactions of a,/?-Unsaturated Aldehydes and Ketones to Trifluoromethyl Substituted Hetero-l,3-dienes

1982 ◽  
Vol 37 (12) ◽  
pp. 1669-1671 ◽  
Author(s):  
Klaus Burger ◽  
Wolfgang Schöntag ◽  
Ulrike Wassmuth
Keyword(s):  
Double Bond ◽  
Carbonyl Compounds ◽  
Cycloaddition Reactions ◽  
Unsaturated Aldehydes ◽  
Aldehydes And Ketones

[4+2]-Cycloaddition reactions of 4,4-bis- (trifluoromethyl)-substituted hetero-1,3-dienes (1-3) to a, β-unsaturated carbonyl compounds (acroleine, methacroleine, cinnamaldehyde, phenylacetylenecarbaldehyde, methylvinylketone) were found to occur across the CO double bond exclusively.

Phosphonium-Based Ionic Liquids as Efficient Borane Carriers

2006 ◽  
Vol 59 (5) ◽  
pp. 298 ◽  
Author(s):  
Taramatee Ramnial ◽  
Michelle K. Hauser ◽  
Jason A. C. Clyburne
Keyword(s):  
Ionic Liquids ◽  
Porous Materials ◽  
Convenient Method ◽  
Carbonyl Compounds ◽  
Gas Transport ◽  
Boron Hydrides ◽  
Reduction Reactions ◽  
Reactive Gas

Phosphonium-based ionic liquids form new ionic liquids when treated with borane (BH3), and these ionic liquids are useful for reduction reactions involving carbonyl compounds. Alane (AlH3) reacts with the phosphonium cation, nevertheless the resulting solutions are capable of reducing esters to aldehydes. Phosphonium-based ionic liquids may serve as useful materials for reactive gas transport, and hence may serve as a fluid alternative to porous materials and may provide a convenient method of safely transporting boron hydrides for a variety of applications.

Cyanoethylations and Michael additions. V. The synthesis of allylic cyclohexenols by γ-cyanoethylation of α,β-unsaturated aldehydes and ketones. Part V

1970 ◽  
Vol 48 (21) ◽  
pp. 3425-3439 ◽  
Author(s):  
Ch. R. Engel ◽  
V. S. Salvi ◽  
L. Ruest
Keyword(s):  
Reaction Time ◽  
Steric Hindrance ◽  
Carbonyl Compounds ◽  
Transfer Reaction ◽  
Main Reaction ◽  
Reaction Products ◽  
Enol Ethers ◽  
Michael Additions ◽  
Unsaturated Aldehydes ◽  
Aldehydes And Ketones

It is shown that the cyanoethylation of 3β-acetoxy-21-methyl-5α-pregn-17-en-21-one results in part in the addition of acrylonitrile to the γ-position, with concomitant cyclization, and that therefore the cyclo-γ-cyanoethylations of α,β-unsaturated carbonyl compounds reported previously were not confined to aldehydes. However, the main reaction products of the conjugated ketone were α-cyanoethylated derivatives. A variation of the reaction time did not affect the proportion of α- and γ-cyanoethylated products; the implications of this finding on mechanistic considerations are discussed; in particular, an explanation based on the assumption of an equilibrium between reactants and α- and γ-cyanoethylated products is ruled out. It is shown that the γ-additions observed, particularly in the case of α,β-unsaturated aldehydes, are not due to steric hindrance, neither to an abnormal charge distribution in the anion. It is further shown that in the presence of base the propionitrile moiety of oxygen-cyanoethylated α,β-unsaturated aldehydes with a suitable geometry is transferred to the γ-position of the original aldehyde and that cyclization occurs so that the same products are obtained from such cyano-enol ethers as in the direct cyanoethylation of the free aldehydes. On the basis of this finding, a mechanism for the cyclo-γ-cyanoethylations of α,β-unsaturated carbonyl compounds, involving such a transfer reaction, can be tentatively proposed.

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