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(Difluoromethyl)trimethylsilane (TMSCHF2): A Useful Difluoromethylating Nucleophilic Source

Authors: Miele M.; Pace V.;

(Difluoromethyl)trimethylsilane (TMSCHF2): A Useful Difluoromethylating Nucleophilic Source

Abstract

Significant advancements have been achieved due to the excellent versatility of the commercially available (difluoromethyl)trimethylsilane (TMSCHF2) as a competent donor of the CHF2 group under nucleophilic regime.[2] It is a commercially or easily accessible liquid documenting excellent experimental manipulability due to its relatively high boiling point. Researchers have used TMSCHF2 for the delivery of the CHF2 unit to Weinreb amides en route to difluoromethyl-ketones. The activation of TMSCHF2 with potassium tertamylate (t-AmOK) ensured higher yields compared with different Lewis bases, enabling an efficient synthesis of these ketones under full chemocontrol, as evidenced in the case of variously functionalized acylating linchpins. Taking advantage of the versatility of using isocyanates and isothiocyanates in forging (thio)-amidic linkages, researchers used TMSCHF2 activated with t-AmOK for preparing in a single synthetic operation difluoromethyl analogues with very high chemoselectivity.

Country
Italy
Keywords

cross-coupling; difluoromethyl; fluorination; fluorine; nucleophilic addition; nucleophilic substitution; organosilicon compounds; silicon

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    influence
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selected citations
These citations are derived from selected sources.
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
13
Top 10%
Average
Top 10%
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