Decarboxylative Umpolung Synthesis of Amines from Carbonyl Compounds

Synlett ◽  
2020 ◽  
Vol 31 (16) ◽  
pp. 1543-1550
Author(s):  
Baoguo Zhao ◽  
Wen-Wen Chen

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

1969 ◽  
Vol 47 (19) ◽  
pp. 3705-3707 ◽  
Author(s):  
D. V. Ramana ◽  
C. N. Pillai

Alumina containing about 2.2% by weight of Na+ has been found to be an effective catalyst for the vapor phase reduction of carbonyl compounds by alcohols and for the reverse reaction, the oxidation of the alcohols by carbonyl compounds. The reduction of a number of aliphatic and aromatic aldehydes and ketones by isopropyl alcohol and the oxidation of a number of primary and secondary alcohols by ketones like acetone and cyclohexanone are reported.


2006 ◽  
Vol 61 (10) ◽  
pp. 1275-1281 ◽  
Author(s):  
Davood Setamdideh ◽  
Behzad Zeynizadeh

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


2021 ◽  
Vol 8 (7) ◽  
pp. 210142
Author(s):  
Melina C. Ontivero ◽  
Teodoro S. Kaufman ◽  
Iván Cortés ◽  
Andrea B. J. Bracca

Methoximes are important as a class of intermediates and products, among fine chemicals and specialties. The development of a new, facile and efficient method for their synthesis is reported. The methoximes were properly accessed from the corresponding aromatic aldehydes and ketones in good to excellent yields, under mild conditions, employing the inexpensive and environmentally friendly MnCl 2 .4H 2 O as a catalyst (at low loading and without the addition of ligand), in EtOH at 50°C. The scope of the process was systematically assessed.


2005 ◽  
Vol 60 (4) ◽  
pp. 453-457 ◽  
Author(s):  
Behzad Zeynizadeh ◽  
Tarifeh Behyar

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


Synthesis ◽  
2019 ◽  
Vol 51 (17) ◽  
pp. 3305-3312 ◽  
Author(s):  
Iryna D. Alshakova ◽  
Georgii I. Nikonov

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.


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