1334709-37-3Relevant academic research and scientific papers
Remote Nickel-Catalyzed Cross-Coupling Arylation via Proton-Coupled Electron Transfer-Enabled C-C Bond Cleavage
Huang, Long,Ji, Tengfei,Rueping, Magnus
supporting information, p. 3532 - 3539 (2020/02/25)
Cross-coupling reactions for carbon-carbon and carbon-heteroatom bond formation are of great importance in modern chemical synthesis. In addition to classical cross-couplings involving preformed or preactivated coupling partners, more recently breakthroughs have been made in the selective, direct coupling of abundant aliphatic carbon-hydrogen bonds using hydrogen atom transfer reactions in which the bond-dissociation energy is the thermodynamic driving force. The more challenging carbon-carbon bond activation is still rather underdeveloped due to the bond inertness. Herein, we report a mild and general strategy for the activation of a diverse set of readily available cyclic alcohols for the remote and site-specific arylation of ketones via the combination of photoredox-mediated multisite concerted proton-electron transfer (MS-PCET) and nickel catalysis. The current cross-coupling proceeds with the generation of an alkoxy radical utilizing bond-dissociation free energy (BDFE) as the thermodynamic driving force. Subsequently, the resulting remote carbon-centered radicals formed by C-C cleavage merge with the nickel catalytic cycle to create the challenging C(sp3)-C(sp2) bonds.
Ligated regioselective PdII catalysis to access β-aryl-bearing aldehydes, ketones, and β-keto esters
Vellakkaran, Mari,Andappan, Murugaiah M. S.,Kommu, Nagaiah
supporting information; experimental part, p. 4694 - 4698 (2012/09/22)
By employing ligands in the PdII-mediated arylative isomerization of allyl alcohols, a milder and regioselective access to the versatile building blocks β-aryl aldehydes and ketones was developed. This new and chelation-controlled protocol enabled the compatibility of wide range of functionalities to generate dihydrochalcones, α-benzyl-α′- alkyl acetones, dihydrocinnamaldehydes, and α-benzyl β-keto esters (from Baylis-Hillman adducts). A practical multigram synthesis of an intermediate for Propafenone was also demonstrated. Copyright
Double arylation of allyl alcohol via a one-pot heck arylation- isomerization-acylation cascade
Colbon, Paul,Ruan, Jiwu,Purdie, Mark,Mulholland, Keith,Xiao, Jianliang
, p. 5456 - 5459 (2011/12/05)
A one-pot, two-step catalytic protocol has been developed. A regioselective Heck coupling between aryl bromides and allyl alcohol leads to the generation of arylated allyl alcohols that in situ isomerize to give aldehydes, which then undergo an acylation reaction with a second aryl bromide. A variety of aryl bromides can be employed in both the initial Heck reaction and the acylation, providing easy access to a wide variety of substituted dihydrochalcones.
