Allene C(sp(2))-H Activation and Alkenylation Catalyzed by Palladium
dc.contributor.author
Schreib, Benedikt S.
dc.contributor.author
Son, Mina
dc.contributor.author
Aouane, Françoise
dc.contributor.author
Baik, Mu-Hyun
dc.contributor.author
Carreira, Erick M.
dc.date.accessioned
2022-04-19T07:50:28Z
dc.date.available
2021-12-31T03:42:51Z
dc.date.available
2022-04-19T07:50:28Z
dc.date.issued
2021-12-29
dc.identifier.issn
0002-7863
dc.identifier.issn
1520-5126
dc.identifier.other
10.1021/jacs.1c11528
en_US
dc.identifier.uri
http://hdl.handle.net/20.500.11850/522501
dc.description.abstract
The selective transition-metal-mediated activation of C(sp(2))-H bonds of allenes is a formidable challenge because of the competitive, intrinsic reactivity of cumulated double bonds. Herein, we report a Pd-catalyzed C-H alkenylation of electronically unbiased allenes, affording penta-1,2,4-triene products in up to 94% yield. A picolinamide directing group enables the formation of putative allenyl-palladacycles, which subsequently participate in a turnover-limiting Heck-type reaction with electron-deficient alkene coupling partners. This mechanistic proposal is consistent with experimental and computational investigations. Additionally, we report for the first time the use of picolinamide N,O-acetals as readily removable auxiliaries for C-H activation reactions, allowing the efficient alkenylation of allenyl carbinol derivatives. Successful removal of the directing groups without affecting the reactive penta-1,2,4-triene substructure of the products is demonstrated.
en_US
dc.language.iso
en
en_US
dc.publisher
American Chemical Society
dc.title
Allene C(sp(2))-H Activation and Alkenylation Catalyzed by Palladium
en_US
dc.type
Journal Article
dc.date.published
2021-12-16
ethz.journal.title
Journal of the American Chemical Society
ethz.journal.volume
143
en_US
ethz.journal.issue
51
en_US
ethz.journal.abbreviated
J. Am. Chem. Soc.
ethz.pages.start
21705
en_US
ethz.pages.end
21712
en_US
ethz.identifier.wos
ethz.identifier.scopus
ethz.publication.place
Washington, DC
ethz.publication.status
published
en_US
ethz.date.deposited
2021-12-31T03:43:48Z
ethz.source
WOS
ethz.eth
yes
en_US
ethz.availability
Metadata only
en_US
ethz.rosetta.installDate
2022-04-19T07:50:35Z
ethz.rosetta.lastUpdated
2024-02-02T16:42:19Z
ethz.rosetta.versionExported
true
ethz.COinS
ctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.atitle=Allene%20C(sp(2))-H%20Activation%20and%20Alkenylation%20Catalyzed%20by%20Palladium&rft.jtitle=Journal%20of%20the%20American%20Chemical%20Society&rft.date=2021-12-29&rft.volume=143&rft.issue=51&rft.spage=21705&rft.epage=21712&rft.issn=0002-7863&1520-5126&rft.au=Schreib,%20Benedikt%20S.&Son,%20Mina&Aouane,%20Fran%C3%A7oise&Baik,%20Mu-Hyun&Carreira,%20Erick%20M.&rft.genre=article&rft_id=info:doi/10.1021/jacs.1c11528&
Files in this item
Files | Size | Format | Open in viewer |
---|---|---|---|
There are no files associated with this item. |
Publication type
-
Journal Article [133575]