221103-69-1Relevant articles and documents
Palladium-catalyzed chemoselective aminomethylative cyclization and aromatizing allylic amination: Access to functionalized naphthalenes
Yu, Bangkui,Yu, Houjian,Huang, Hanmin
, p. 8962 - 8966 (2020/11/13)
A palladium-catalyzed chemoselective aminomethylative cyclization and aromatizing allylic amination of enyne-tethered allylic alcohols with aminals is described. Under the reaction conditions, the cationic vinyl allylpalladium species undergoes selective migratory insertion of alkenes rather than reductive elimination with nucleophiles. This strategy provides an efficient and unique approach to the construction of functionalized naphthalenes, which are important building blocks in synthetic organic chemistry. Mechanistic studies have revealed that the selective sequential migratory insertion of enyne and alkene is crucial for the cyclization.
Synthetic and Mechanistic Investigation of an Oxime Ether Electrocyclization Approach to Heteroaromatic Boronic Acid Derivatives
Mora-Radó, Helena,Sotorríos, Lia,Ball-Jones, Matthew P.,Bialy, Laurent,Czechtizky, Werngard,Méndez, María,Gómez-Bengoa, Enrique,Harrity, Joseph P. A.
, p. 9530 - 9534 (2018/07/14)
A range of functionalized heteroaromatic boronic acid derivatives are readily accessed by a diboration/6π-electrocyclization sequence. This study revealed the surprising observation that there is a direct relationship between oxime ether stereochemistry and reactivity towards electrocyclization. Specifically, E-oxime ethers are found to be significantly more reactive than their Z-counterparts (stereochemistry relative to azatriene scaffold). In contrast, the configuration at the azatriene alkene terminus has little impact on reaction rates. Computational analysis offers a rationale for this observation; a Nlone pair→C=C π* orbital interaction lowers the energy of the transition state in the electrocyclization of E-oxime ethers. Finally, unreactive Z-oxime ethers can be converted to the corresponding heterocyclic products by a photolytically promoted E→Z isomerization and electrocyclization sequence.
One-pot synthesis of aromatic fused 2,3-dihydroindanone by tandem Pauson-Khand/Michael/Henry reaction
Li, Mingming,Xing, Ping,Huang, Zuogang,Jiang, Biao
, p. 49 - 54 (2013/08/24)
The intermolecular Pauson-Khand reaction between 2-ethynylbenzaldehyde and ethylene promoted by dimethyl sulfide can be utilized to synthesize 2-(2-formylphenyl)cyclopentenone efficiently. This compound and its derivatives undergo a cascade process of Michael addition reaction followed by Henry reaction with nitromethane to construct substituted aromatic fused 2,3-dihydroindanones. Furthermore, direct one-pot synthesis of aromatic fused 2,3-dihydroindanones from 2-ethynylbenzaldehyde is achieved. Copyright
