Remote Alkynylation of Aliphatic Amines

Advancements in transition metal catalyzed C-H activation/functionalization cascades have allowed the synthetic chemist's toolbox to be significantly expanded. Despite this, protocols for the remote alkynylation of linear aliphatic amines still remain limited. Herein, a palladium-catalyzed directing-group approach to alkynylation of aliphatic amines is disclosed. The synthetic utility was demonstrated with a gram-scale reaction and a functional group compatibility test.

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Publication Details

Journal
Organic Letters
Published
2024-11-27
DOI
https://doi.org/10.1021/acs.orglett.4c03468
Citations
3
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.75
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article

Remote Alkynylation of Aliphatic Amines

Peter D. Smith, Rachel H. Munday, Elizabeth M. Dauncey, Tom D. Sheppard
3 citations
Organic Letters
Catalytic C–H Functionalization Methods
0.75
article

Remote Alkynylation of Aliphatic Amines

Peter D. Smith, Rachel H. Munday, Elizabeth M. Dauncey, Tom D. Sheppard
article en
3 citations

Abstract

Advancements in transition metal catalyzed C-H activation/functionalization cascades have allowed the synthetic chemist's toolbox to be significantly expanded. Despite this, protocols for the remote alkynylation of linear aliphatic amines still remain limited. Herein, a palladium-catalyzed directing-group approach to alkynylation of aliphatic amines is disclosed. The synthetic utility was demonstrated with a gram-scale reaction and a functional group compatibility test.

Organic LettersVol. 26(49)
AstraZeneca (Singapore) (SG), AstraZeneca (Poland) (PL), University College London (GB)
Openalex Percentile: Top 31%
Catalytic C–H Functionalization Methods
0.75
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