285571-20-2Relevant academic research and scientific papers
Direct intramolecular arylation of aldehydes promoted by reaction with IPy2BF4/HBF4: Synthesis of benzocyclic ketones
Barluenga, Jose,Trincado, Monica,Rubio, Eduardo,Gonzalez, Jose M.
, p. 3140 - 3143 (2007/10/03)
(Chemical Equation Presented) Iodine helps: Aldehydes acylate arenes upon treatment at low temperature with IPy2BF4 and HBF 4. This reaction is exploited in a novel intramolecular approach to the preparation of benzocyclic ketones (see scheme). A plausible mechanistic rational is also given.
New synthetic approaches to polycyclic aromatic hydrocarbons and their carcinogenic oxidized metabolites: Derivatives of benzo[s]picene, benzo[rst]pentaphene, and dibenzo[b,def]chrysene
Zhang, Fang-Jie,Cortez, Cecilia,Harvey, Ronald G.
, p. 3952 - 3960 (2007/10/03)
A new synthetic approach to polycyclic aromatic compounds is described that entails in the key steps double Suzuki coupling of PAH bisboronic acid derivatives with o-bromoaryl aldehydes to furnish aryl dialdehydes that are converted to larger polycyclic aromatic ring systems by either (a) conversion to diolefins by Wittig reaction followed by photocyclization or (b) reductive cyclization with triflic acid and 1,3-propanediol. This synthetic method provides convenient access to as many as three different polycyclic aromatic ring systems from a single Suzuki coupled intermediate. It was utilized to synthesize substituted derivatives of benzo[s]picene, benzo[rst]pentaphene, dibenzo-[b,def]chrysene, and 13,14-dihydro-benz[g]indeno[2,1-a]fluorene, as well as the putative carcinogenic bisdihydrodiol metabolites of benzo[s]picene, benzo[rst]pentaphene, and dibenzo[b,def]chrysene.
