Hydrogen fluoride triethylamine complex

The 5 (or 6) hydrogen fluoride/triethylamine complex can also be used as a mild and selective hydrofluorination agent for preparing tertiary alkyl fluorides. ... 

Removal of the TBDPS ether in intermediate 71.1 en route to Myxovirescin A1 [Scheme 4.71] gave the desired alcohol 71.2 along with the acyl migration product 7U. 2 With TBAF, a 1 1 mixture of 71.2 and 71J was obtained but the rearrangement was minimised to 10% using the hydrogen fluoride-triethylamine complex at room temperature. 

The trimethylsilyl protecting group can be removed by routine deprotection with triethylamine -hydrogen fluoride complex. 

Hydrazones are transformed into gcw-difluoro compounds by treatment with a combination of 60% hydrogen fluoride/pyridine or 59% hydrogen fluoride/poly-4-vinylpyridine and N-bromosuccinimide yields are satisfactory.170 The electrochemical reaction of diarylketone hydrazones 1 in the presence of triethylamine trisfhydrogen fluoride) complex in dichloromethane solution (current density 1.3 mA cm"2) gives mainly the monofluorinated products 2 besides only very small amounts of difluorides 3.332... 

Elimination of hydrogen fluoride from vinylic fluoride 16. using the triethylamine-boron trifluoride complex, yields the allene 17.96... 

Methyl perfluoromethacrylate reacts with allyl and propargyl alcohols to give the Michael addition products 19 and 20, respectively these eliminate hydrogen fluoride in the presence of the boron trifluoride-triethylamine complex and rearrange to acyl fluorides 21 and 22. Hydrolysis of the acyl fluorides with base results in decarboxylation to give the 2-(trifluoromethyl) esters 23 and 24.11... 

The bromofluorination of norbornadiene using A-bromosuccinimide in the presence of triethylamine-tris(hydrogen fluoride) complex (EtjN 3HF), a highly versatile and easy to handle source of fluoride ions, gave in near quantitative yield a mixture of exo-3-bromo-... 

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