Tetrabutylammonium fluoride-induced conversion of tresylates to mesylates

Seong Choe Yearn; John A. Katzenellenbogen

doi:10.1016/0040-4039(93)85011-K

Tetrabutylammonium fluoride-induced conversion of tresylates to mesylates

Seong Choe Yearn
, John A. Katzenellenbogen

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Reaction of secondary 2,2,2-trifluoroethanesulfonate ester (tresylates) with tetrabutylammonium flouride (TBAF) gives methanesulfonate esters (mesylates) in yields of 60-65%. A possible mechanism for this reaction includes TBAF-induced dehydroflourination followed by hydration and hydrolysis effected by the water in TBAF (1 M in THF), and subsequently decarboxylation. This study show some limitations on the use of tresylates as leaving groups for flourine substitution in nucleophilic displacement reactions.

Original language	English (US)
Pages (from-to)	1579-1580
Number of pages	2
Journal	Tetrahedron Letters
Volume	34
Issue number	10
DOIs	https://doi.org/10.1016/0040-4039(93)85011-K
State	Published - Mar 5 1993

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/0040-4039(93)85011-K

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title = "Tetrabutylammonium fluoride-induced conversion of tresylates to mesylates",

abstract = "Reaction of secondary 2,2,2-trifluoroethanesulfonate ester (tresylates) with tetrabutylammonium flouride (TBAF) gives methanesulfonate esters (mesylates) in yields of 60-65\%. A possible mechanism for this reaction includes TBAF-induced dehydroflourination followed by hydration and hydrolysis effected by the water in TBAF (1 M in THF), and subsequently decarboxylation. This study show some limitations on the use of tresylates as leaving groups for flourine substitution in nucleophilic displacement reactions.",

author = "Yearn, \{Seong Choe\} and Katzenellenbogen, \{John A.\}",

note = "In conclusion, we report a limitation on the use of tresylates as activating, groups for secondary alcohols . Under conditions known to effect the displacement of primary tresylates by fluoride ion (TBAF),9 secondary tresylates are instead converted to mesylates. Acknowledgment. We are grateful for support of this research through a grant from the Department of Energy (DE FG02 86ER60401) .",

year = "1993",

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doi = "10.1016/0040-4039(93)85011-K",

language = "English (US)",

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journal = "Tetrahedron Letters",

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number = "10",

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T1 - Tetrabutylammonium fluoride-induced conversion of tresylates to mesylates

AU - Yearn, Seong Choe

AU - Katzenellenbogen, John A.

N1 - In conclusion, we report a limitation on the use of tresylates as activating, groups for secondary alcohols . Under conditions known to effect the displacement of primary tresylates by fluoride ion (TBAF),9 secondary tresylates are instead converted to mesylates. Acknowledgment. We are grateful for support of this research through a grant from the Department of Energy (DE FG02 86ER60401) .

PY - 1993/3/5

Y1 - 1993/3/5

N2 - Reaction of secondary 2,2,2-trifluoroethanesulfonate ester (tresylates) with tetrabutylammonium flouride (TBAF) gives methanesulfonate esters (mesylates) in yields of 60-65%. A possible mechanism for this reaction includes TBAF-induced dehydroflourination followed by hydration and hydrolysis effected by the water in TBAF (1 M in THF), and subsequently decarboxylation. This study show some limitations on the use of tresylates as leaving groups for flourine substitution in nucleophilic displacement reactions.

AB - Reaction of secondary 2,2,2-trifluoroethanesulfonate ester (tresylates) with tetrabutylammonium flouride (TBAF) gives methanesulfonate esters (mesylates) in yields of 60-65%. A possible mechanism for this reaction includes TBAF-induced dehydroflourination followed by hydration and hydrolysis effected by the water in TBAF (1 M in THF), and subsequently decarboxylation. This study show some limitations on the use of tresylates as leaving groups for flourine substitution in nucleophilic displacement reactions.

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U2 - 10.1016/0040-4039(93)85011-K

DO - 10.1016/0040-4039(93)85011-K

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JO - Tetrahedron Letters

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IS - 10

ER -

Tetrabutylammonium fluoride-induced conversion of tresylates to mesylates

Abstract

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