131190-07-3Relevant academic research and scientific papers
THF: An efficient electron donor in continuous flow radical cyclization photocatalyzed by graphitic carbon nitride
Wonica, Magdalena,Chaoui, Nicolas,Taabache, Soraya,Blechert, Siegfried
, p. 14624 - 14628 (2014)
Mesoporous graphitic carbon nitride (mpg-C3N4) was found to be an efficient heterogeneous photocatalyst for the metal-free radical cyclization of 2-bromo-1,3-dicarbonyl compounds. Reactions leading to functionalized cyclopentanes pro
Pd-catalyzed intramolecular addition of active methylene compounds to alkynes with subsequent cross-coupling with (hetero)aryl halides
B?ocka, Aleksandra,Wo?nicki, Pawe?,Stankevi?, Marek,Cha?adaj, Wojciech
, p. 40152 - 40167 (2019/12/25)
We report an efficient protocol for tandem Pd-catalyzed intramolecular addition of active methylene compounds to alkynes, followed by subsequent cross-coupling with (hetero)aryl bromides and chlorides. The reaction proceeds under mild conditions, providing excellent functional group tolerance, including unprotected OH, NH2 groups, enolizable ketones, or a variety of heterocycles. Mechanistic studies point towards a catalytic cycle involving oxidative addition, intramolecular nucleophilic addition to the Pd(ii)-activated alkyne, and reductive elimination, with 5-exo-dig cyclization being the rate limiting step.
An X- (X = I, Br)-triggered ring-opening cyclization of cyclopropenyl-substituted alkyl halides or mesylates: An efficient and highly regioand stereoselective approach to (E)-haloalkylidene 4-7-membered cyclic compounds
Chen, Jie,Ma, Shengming
supporting information; experimental part, p. 5595 - 5598 (2009/12/03)
(Chemical Equation Presented) Polyfunctionalized (E)-haloalkylidene cyclic products were efficiently synthesized in moderate to excellent yields via a regio- and stereoselective X- (X = I or Br)-triggered ring-opening intramolecular trapping of
The synthesis of (E)-arylidene and allylidene cyclopentanes by means of a pallodium(0)-catalyzed complex
Fournet,Balme,Gore
, p. 6293 - 6304 (2007/10/02)
When treated with an unsaturated halide in a palladium-catalyzed process, the anions from γ-acetylenic malonates 4 and 5 stereospecifically lead to cyclopentanes having an exo tri- or tetra-substituted double bond. This reaction which forms simultaneously two carbon-carbon bonds is believed to proceed by nucleophilic attack of the anion on the triple bond activated by the σ-aryl or σ-vinyl palladium complex.
Stereospecific synthesis of arylidene and allylidene cyclopentanes by a palladium-catalyzed cylisation
Fournet, Guy,Balme, Genevieve,Van Hemelryck, Bruno,Gore, Jacques
, p. 5147 - 5150 (2007/10/02)
Vinyl and aryl halides react with ε-acetylenic β-diesters, β-keto esters and βsulfonylesters in the presence of a Pd(o) catalyst leading in good yields to the title compounds. The acetylenic homolog containing an additional carbon leads in the same conditions to a cyclohexane, but this process then competes with the arylation of the terminal acetylenic carbon.
