Gore, Babasaheb Sopan; Lin, Jun-Hao; Wang, Jeh-Jeng published the artcile< Unraveling innate substrate-controlled arylation and bicyclization of 1,5-enynes with α,β conjugates: synthesis of substituted benzo[a]fluorenes>, Category: nitriles-buliding-blocks, the main research area is enyne unsaturated ketone arylation arene cyclization Friedel Crafts; benzofluorene aryl regioselective preparation green chem.
A strategy for the aromatic C-H functionalization of electron-rich arenes, such as anisole, phenol, veratrol, toluene or naphthalene, with 1,5-enynes anchored by conjugates, e.g., I (X = CN, EtO2C, Ts, PhCO; R1 = n-Bu, Ph, 3-FC6H4, etc.; R2 = H, 4-Me, 5-F, 4-MeO, etc.; R3 = H, 4-Cl, 3-F, 3-Br, etc.) catalyzed by a Bronsted acid under metal- and solvent-free conditions has been developed. A diverse range of benzo[a]fluorenes, e.g., II [R4 = 4-MeOC6H4, 4-HOC6H4, 3,4-(MeO)2C6H3] [from I (X = CN)] or III (R4 = 4-MeOC6H4, 4-MeC6H4, 1-naphthyl), was obtained in moderate to good yields by using this protocol. This process includes intermol. nucleophilic arene insertion or 6-exo-dig cyclization (depending on the nature of the substrates) followed by a Friedel-Crafts-type reaction and 1,5-H transfer or intermol. nucleophilic arene insertion, resp. In addition, reactions with heterocyclic compounds such as (E)-2-benzoyl-3-(2-(phenylethynyl)pyridin-3-yl)acrylonitrile proceeded smoothly and afforded 11-phenyl-11H-indeno[1,2-h]quinoline-6-carbonitrile. Moreover, solvent recycling experiments were successfully carried out to illustrate green pathways. These reactions feature a readily accessible starting materials, transition metal-free approaches, simple one-pot operations, gram-scale syntheses and wide functional group tolerance.
Green Chemistry published new progress about Alkenynes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, Category: nitriles-buliding-blocks.
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts