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1 2003

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Zastosowanie trietyloaminy w syntezie organicznej

Kowalski P., Sikorska-Jarosz J.

Wiadomości Chemiczne

2003

[Z] 57, 11-12

1133--1162

This review shows examples of application of Et3N in oxidations, eliminations, substitutions, and addition reactions. Triethylamine (Et3N) appears to be most popular organic amine base in organic synthetic chemistry. The popularity comes from its low price along with easiness of removal by distillation. However, Et3N is a very dangerous fire hazard when exposed to the heat, flame, or oxidizers. Their salts with inorganic acids are somewhat insoluble in most organic solvents of low polarity and for that reason may by removed from the reaction media by simple filtration. Examples of application of Et3N in oxidation reactions are shown in ozonolysis of cycloalkene 1-8 [3-5] (figs 1-4-5), and figs 1-6-8 show oxidation of 1-14, 1-16, and 1-18 alcohols, employing activated DMSO [6-12]. Various oxidation processes of hydrazones with iodide in the presence of Et3N are presented in fig. 1-9 [13]. Elimination reactions, concerned mainly with dehydrohalogenations, are described in examples of halogen derivatives of lactone 2-1 [17], ketone 2-3 [18,19], sulfone 2-6 [20], and acids 2-9 and 2-11 [21,22] (figs 2-1-5). Dehalogenation of 2-13 [23], 2-17 [26-28], and 2-22 [31-37] acid chlorides are presented in figs 2-6-8, while formation of nitrile oxides in figs 2-11-13 [38-42]. Competitive dehydrobromination and dehydrochlorination reaction occurs in the presence of Et3N in 1,1,1-trichloro-3-bromo-3-fenylopropane (2-35) is described in fig. 2-15 [44]. Mechanizm and examples of transformation of chlorosulfonyl chlorides are presented in figs 2-17-20 [47-51], and dimerization of aldiminium salts [63] in fig. 2-25 as well. Applications of Et3N in carbon-carbon bond formation in an intramolecular Heck reaction are shown in fig. 3-1 [70-74]. Example of use of Et3N in enolboronation of carbonyl compounds is described in fig. 3-2 [75-78], and additionally, in synthesis of silyl enol ethers can be found in figs 3-3-6 [89-104]. Application of Et3N as the base in neutralizing the acids liberated in preparing diazo ketones and mixed anhydrides are indicated in fig. 3-7 [105-107] and fig. 3-8 [108-117] respectively, while in protecting of hydroxy group in figs 3-9-11 [118-126]. Use of Et3N as the effective catalyst in cyjanoethylation reaction of active methyl group in acetylacetone (4-2) [130] and alkylpyridine methiodides 4-4-5, 4-8-9 [131] are shown in figs 4-1-3, and in isomerization reaction of pyrazolines 4-14 [133] and cycloaddition of indane-1,3-dione (4-16) [134] in figs.4-5?6.