Sandra Forbes

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Trimethylamine borane, also known as trimethylamine complex with borane or trimethylamine borane adduct, is a chemical compound with the formula (CH3)3N·BH3. It is a coordination complex formed by the reaction between trimethylamine (N(CH3)3) and borane (BH3).

This compound is notable for its utility in organic synthesis, particularly as a reducing agent. The borane moiety (BH3) is a strong Lewis acid, while trimethylamine (N(CH3)3) serves as a source of nucleophilic nitrogen. The combination of these properties makes trimethylamine borane useful for various organic transformations, including reductions of aldehydes, ketones, and imines to their corresponding alcohols or amines.

Trimethylamine borane is typically handled as a colorless to yellowish solid and is often used in solution in solvents such as diethyl ether or tetrahydrofuran (THF). It is an air-sensitive compound and should be stored and handled under inert conditions to prevent decomposition or oxidation.

In addition to its synthetic applications, trimethylamine borane has found use in various other fields, including as a reagent in the purification of gases, as a hydrogen storage material, and as a precursor for boron-containing compounds.

Recent Literature

The use of trimethylamine-borane facilitates a six-electron reduction of CO2 for a highly selective monomethylation of 2-arylacetonitrile derivatives. Various 2-arylpropionitriles were obtained in good yields.

X. Zhang, S. Wang, C. Xi, J. Org. Chem., 2019, 84, 9744-9749.

DOI: 10.1021/acs.joc.9b01587

Metal-free reductive N-trifluoroethylation and N-trifluoroacetylation of indoles provide trifluoroethylated or trifluoroacetylated indolines depending on the loading of trimethylamine borane as reducing agent and TFA as trifluoroethyl or trifluoroacetyl source, respectively.

Y.-F. Zeng, M.-X. Zhou, Y.-N. Li, X. Wu, Y. Guo, Z. Wang, Org. Lett., 2022, 24, 7440-7445.

DOI: 10.1021/acs.orglett.2c03011

Quoted from: https://www.organic-chemistry.org/chemicals/reductions/trimethylamine-borane.shtm

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