“…13 In turn methods developed in last few years utilize more sophisticated reagents designed for direct conversion of carboxylic acids under mild conditions. [14][15][16][17][18][19][20] However, the latter approach usually suffers from high cost of the reagents, low atom economy, and the formation of significant amounts of waste, and thus is only suitable for transformations of more valuable substrates. At the same time, convenient synthesis of simple alkanoyl and aroyl fluorides on a multigram scale remains rather lacking.…”
A series of acyl fluorides was synthesized at 100 mmol scale using phase transfer catalyzed halogen exchange between acyl chlorides and aqueous bifluoride solution. The convenient procedure consists of vigorous stirring of the biphasic mixture at rt, followed by extraction and distillation. Isolated acyl fluorides (usually 7 g to 20 g) display excellent purity, and can be transformed into sterically hindered amides and esters, when treated with lithium amide bases and alkoxides under mild conditions.
“…13 In turn methods developed in last few years utilize more sophisticated reagents designed for direct conversion of carboxylic acids under mild conditions. [14][15][16][17][18][19][20] However, the latter approach usually suffers from high cost of the reagents, low atom economy, and the formation of significant amounts of waste, and thus is only suitable for transformations of more valuable substrates. At the same time, convenient synthesis of simple alkanoyl and aroyl fluorides on a multigram scale remains rather lacking.…”
A series of acyl fluorides was synthesized at 100 mmol scale using phase transfer catalyzed halogen exchange between acyl chlorides and aqueous bifluoride solution. The convenient procedure consists of vigorous stirring of the biphasic mixture at rt, followed by extraction and distillation. Isolated acyl fluorides (usually 7 g to 20 g) display excellent purity, and can be transformed into sterically hindered amides and esters, when treated with lithium amide bases and alkoxides under mild conditions.
“…becoming increasingly important and valuable fluorinating agents due to their unique balance of stability and reactivity. [51][52][53][54] Furthermore, the reaction of 2 with trimethysilyl iodide produces trimethylsilyl fluoride, a silylating agent for ketones, alcohol, terminal alkynes and various lithiated precursors. 55-59 2 also reacted with BCl3 to produce a series of commercially relevant Lewis acids.…”
<b>The room-temperature activation of SF<sub>6</sub>, a potent greenhouse gas, is reported using a monovalent aluminium(I) reagent to form well-defined aluminium(III) fluoride and aluminium(III) sulfide products. New reactions have been developed to utilise the aluminium(III) fluoride and aluminium(III) sulfide as a nucleophilic source of F<sup>–</sup> and S<sup>2– </sup>for a range of electrophiles. The overall reaction sequence results in the net transfer of fluorine or sulfur atoms from an environmentally detrimental gas to useful organic products.</b>
“…Acyl fluorides are becoming increasingly important and valuable fluorinating agents due to their unique balance of stability and reactivity. [51][52][53][54] Furthermore, the reaction of 2 with trimethysilyl iodide produces trimethylsilyl fluoride, a silylating agent for ketones, alcohol, terminal alkynes and various lithiated precursors. 55-59 2 also reacted with BCl3 to produce a series of commercially relevant Lewis acids.…”
The room-temperature activation of SF6, a potent greenhouse gas, is reported using a monovalent aluminium(I) reagent to form well-defined aluminium(III) fluoride and aluminium(III) sulfide products. New reactions have been developed...
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