Carboxylate-Catalyzed C-Silylation of Terminal Alkynes
Year of publication
2024
Authors
Bannykh, Anton; Pihko, Petri M.
Abstract
A carboxylate-catalyzed, metal-free C-silylation protocol for terminal alkynes is reported using a quaternary ammonium pivalate as the catalyst and commercially available N,O-bis(silyl)acetamides as silylating agents. The reaction proceeds under mild conditions, tolerates a range of functionalities, and enables concomitant O- or N-silylation of acidic OH or NH groups. A Hammett ρ value of +1.4 ± 0.1 obtained for para-substituted 2-arylalkynes is consistent with the proposed catalytic cycle involving a turnover-determining deprotonation step.
Show moreOrganizations and authors
Publication type
Publication format
Article
Parent publication type
Journal
Article type
Original article
Audience
ScientificPeer-reviewed
Peer-ReviewedMINEDU's publication type classification code
A1 Journal article (refereed), original researchPublication channel information
Journal/Series
Publisher
Volume
26
Issue
10
Pages
1991-1995
ISSN
Publication forum
Publication forum level
2
Open access
Open access in the publisher’s service
Yes
Open access of publication channel
Partially open publication channel
Self-archived
Yes
Article processing fee (EUR)
4013
Year of payment for the open publication fee
2024
Other information
Fields of science
Chemical sciences
Keywords
[object Object],[object Object],[object Object]
Publication country
United States
Internationality of the publisher
International
Language
English
International co-publication
No
Co-publication with a company
No
DOI
10.1021/acs.orglett.3c04213
The publication is included in the Ministry of Education and Culture’s Publication data collection
Yes