Reactions of t-Boc-Protected Amines with Difluorocarbene

The reactions of t-Boc-protected secondary and primary amines with difluorocarbene generated from trimethylsilyl (fluorosulfonyl) difluoroacetate [ Me3SiOC(O) CF2SO2F] (TFDA) in toluene at 110 degrees C results in the replacement of t-Bu by difluoromethyl in the t-Boc group. This reaction can be car...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 51; no. 12; pp. 2579 - 2583
Main Authors Gerasov, Andrii, Shivanyuk, Alexander, Fetyukhin, Volodymyr, Lukin, Oleg
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.06.2019
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
difluoromethylcarbamate
t-Bu/CHF2 replacement
TFDA
t-Boc group
trimethylsilyl ( fluorosulfonyl) difluoroacetate
FACILE
acylation
UNSYMMETRICAL UREAS
urea
EFFICIENT METHOD
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Summary:The reactions of t-Boc-protected secondary and primary amines with difluorocarbene generated from trimethylsilyl (fluorosulfonyl) difluoroacetate [ Me3SiOC(O) CF2SO2F] (TFDA) in toluene at 110 degrees C results in the replacement of t-Bu by difluoromethyl in the t-Boc group. This reaction can be carried out in the presence of CH2Br and COOMe moieties in the structure of the protected amine. In the example of a tBoc- protected amine containing a C= C double bond, replacement of the t-Bu group and/or cyclodifluoropropanation takes place. Difluoromethyl esters are shown to react with primary and secondary amines yielding the corresponding ureas.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0037-1610703