24401-39-6Relevant articles and documents
Metal-Free Oxidative Decarbonylative [3+2] Annulation of Terminal Alkynes with Tertiary Alkyl Aldehydes toward Cyclopentenes
Zou, Hua-Xu,Li, Yang,Yang, Xu-Heng,Xiang, Jiannan,Li, Jin-Heng
, p. 8581 - 8588 (2018)
A new metal-free oxidative decarbonylative [3+2] annulation of terminal alkynes with tertiary alkyl aldehydes is presented, which features broad substrate scope and excellent selectivity. The selectivity of this reaction toward cyclopentenes and indenes relies on the nature of the aldehyde substrates. While treatment of tertiary γ,δ-unsaturated aldehydes with common terminal alkynes assembles cyclopentenes, 2-methyl-2-arylpropanals succeed in accessing indenes.
Nickel-Catalyzed α-Allylation of Aldehydes and Tandem Aldol Condensation/Allylation Reaction with Allylic Alcohols
Bernhard, Yann,Thomson, Brodie,Ferey, Vincent,Sauthier, Mathieu
supporting information, p. 7460 - 7464 (2017/06/13)
An additive-free nickel-catalyzed α-allylation of aldehydes with allyl alcohol is reported. The reaction is promoted by 1 mol % of in situ formed nickel complex in methanol, and water is the sole by-product of the reaction. The experimental conditions allow the conversion of various α-branched aldehydes and α,β-unsaturated aldehydes as nucleophiles. The same catalyst and reaction conditions enabled a tandem aldol condensation of aldehyde/α-allylation reaction.
Activation of alcohols with carbon dioxide: Intermolecular allylation of weakly acidic pronucleophiles
Lang, Simon B.,Locascio, Theresa M.,Tunge, Jon A.
supporting information, p. 4308 - 4311 (2014/11/08)
The direct coupling of allyl alcohols with nitroalkanes, nitriles, and aldehydes using catalytic Pd(PPh3)4 has been accomplished via activation of C-OH bonds with CO2. The in situ formation of carbonates from alcohols and CO2 facilitates oxidative addition to Pd to form reactive π-allylpalladium intermediates. In addition, the formation of a strong base activates nucleophiles toward the reaction with the π-allylpalladium electrophile. Overall, this atom economical reaction provides a new C-C bond without the use of an external base and generates water as the only byproduct.