196-62-3Relevant academic research and scientific papers
Palladium-catalyzed cocyclotrimerization of arynes with a pyramidalized alkene
Alonso, José M.,Quiroga, Sabela,Codony, Sandra,Turcu, Andreea L.,Barniol-Xicota, Marta,Pérez, Dolores,Guitián, Enrique,Vázquez, Santiago,Pe?a, Diego
, p. 5996 - 5999 (2018)
The metal-catalyzed [2+2+2] cocycloaddition of arynes with pyramidalized alkenes is presented. The generation of a highly reactive pyramidalized alkene in the presence of a large excess of in situ-produced arynes led to the corresponding cocyclotrimerization (1:2)-adducts in good yields, establishing the first example of a palladium-based reaction of a pyramidalized alkene.
Highly diastereoselective synthesis of a novel functionalized triepoxytrinaphthylene
Erdo?an, Musa,E?siz, Sel?uk,Fabris, Fabrizio,Da?tan, Arif
, p. 125 - 134 (2018)
The high yielding synthesis of a novel benzocyclotrimer is herein presented. The syn-diastereomer is obtained as major product, presumably in virtue of the presence of an oxa-bridge of the bicylic components. The three oxa-bridges can be used for further functionalization, as well as the six bromine atoms of the three aromatic rings, as demonstrated in the aromatization of a mixture of anti-1 and syn-1 (3:7) leading to trinaphthylene.
Access to polysubstituted naphthalenes and anthracenes via a retro-Diels–Alder reaction
Akin, Esra Turan,Erdogan, Musa,Dastan, Arif,Saracoglu, Nurullah
supporting information, p. 5537 - 5546 (2017/08/22)
Naphthalene and anthracene nuclei are present in several natural and synthetic compounds. Due to their unique physical and chemical properties, access to functionalized naphthalenes and anthracenes has attracted the attention of both synthetic and medicinal chemists over the decades. In this study, successive Diels–Alder/retro-Diels–Alder reactions of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate with various bicyclic alkenes in one pot to yield naphthalene and anthracene derivatives are reported. Using anti- and syn-cyclotrimers derived from the cyclotrimerization of benzobarrelene as alkene partner enabled efficient synthesis of trinaphthylene.
Use of 2-bromophenylboronic esters as benzyne precursors in the Pd-catalyzed synthesis of triphenylenes
Garcia-Lopez, Jose-Antonio,Greaney, Michael F.
supporting information, p. 2338 - 2341 (2014/05/20)
ortho-Substituted aryl boronates are introduced as aryne precursors for transition-metal-catalyzed transformations. On treatment with tBuOK and Pd(0), metal-bound aryne intermediates are formed that undergo effective trimerization to form useful triphenylene compounds. For meta-substituted arynes, the 3:1 product ratio in favor of non-C3 symmetric material is indicative of a benzyne mechanism.
