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First Pd-catalyzed C(sp2)–H / C(sp2)–H coupling of Limonene

08 January 2024, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Limonene undergoes a regioselective Pd(II)-catalyzed C(sp2)–H / C(sp2)–H coupling with acrylic acid esters and amides, alpha,beta-unsaturated ketones, styrenes and allyl acetate, affording novel 1,3-dienes. DFT computations gave results in accord with the experimental results and allowed to formulate a plausible mechanism. The post-functionalization of one of the coupled products was achieved via a large-scale Sonogashira reaction conducted under micellar catalysis.

Keywords

C–H activation
Palladium
Limonene
Silver
DFT

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Version History

Jan 08, 2024 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2024-nzkq1
D O I: 10.26434/chemrxiv-2024-nzkq1 [opens in a new tab]

Funding

European Union’s Horizon 2020 ITN
860762
Fundação para a Ciência e Tecnologia
UIDB/00100/2020
Fundação para a Ciência e Tecnologia
LA/P/0056/2020
Fundação para a Ciência e Tecnologia
UIDP/00100/2020

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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