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ACS Omega

ACS Omega

IF: 3.7
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Density Functional Theory Study on the Selective Reductive Amination of Aldehydes and Ketones over Their Reductions to Alcohols Using Sodium Triacetoxyborohydride

Published:19 August 2022 DOI: 10.1021/acsomega.2c04056 PMID: 36061668
Shannon J. Oliphant, ?and?, Robert H. Morris*, 

Abstract

Reductive amination is one of the most important methods to synthesize amines, having a wide application in the pharmaceutical, fine chemicals, and materials industries. In general, the reaction begins with dehydration between a carbonyl compound and an amine compound, forming an imine, which is then reduced to an alkylated amine product. Sodium triacetoxyborohydride (STAB) is a popular choice for the reducing agent as it shows selectivity for imines over aldehydes and ketones, which is particularly important in direct reductive amination where the imine and carbonyl compounds are present concurrently. Here, we analyze the reaction pathways of acid-catalyzed direct reductive amination in 1,2-dichloroethane (DCE) with acetaldehyde and methylamine. We find that the transition states for the formation and subsequent reduction of Z-methylethylideneimine (resultant aldimine from acetaldehyde and methylamine) have lower energies than the reduction of acetaldehyde. Transition state structures for the hydride transfers are organized by the Lewis-acidic sodium ion. Additionally, reduction reactions with formaldehyde and acetone and their imine derivatives (with methylamine) are investigated, and again, the hydride transfer to the resultant aldimine or ketimine is lower in energy than that of their parent carbonyl compound.

Substances (4)

Related products
Procduct Name CAS Molecular Formula Supplier Price
Formaldehyde 50-00-0 CH2O 902 suppliers $10.00-$1760.00
Sodium triacetoxyborohydride 56553-60-7 C6H10BNaO6 727 suppliers $10.00-$8250.00
1,2-Dichloroethane 107-06-2 C2H4Cl2 505 suppliers $12.70-$1190.00
Acetaldehyde 75-07-0 C2H4O 474 suppliers $14.00-$5150.00

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