1332452-83-1Relevant academic research and scientific papers
Synthesis of substituted helicenes by Ir-catalyzed annulative coupling of biarylcarboxylic acid chlorides with alkynes
Kamikawa, Ken,Den, Hiroakira,Tsurusaki, Akihiro,Nagata, Tomoya,Miura, Masahiro
, p. 1069 - 1074 (2018)
A series of substituted [4] and [5]helicenes were synthesized in moderate to good yields by an Ir-catalyzed annulative coupling of biarylcarboxylic acid chlorides with internal alkynes, which involves facile C-H bond cleavage and decarbonylation. The double annulative coupling of 1, 1′:5′, 1″-ternaphthalene- 2, 2″-dicarboxylic acid dichloride with 4-octyne was also accomplished to give rise to an S-shaped double helicene. Unexpectedly, a π-extended benzofluoranthene-merged [5]- helicene was constructed through the annulative coupling and the successive C(aryl)-C(aryl) bond forming reaction when 1, 1′:4′, 1″-ternaphthalene-2, 2″-dicarboxylic acid dichloride was employed as the substrate. The crystal structure and the optical properties of the latter unique product were also investigated.
METHOD FOR PREPARING CHEMICAL COMPOUNDS OF INTEREST BY NUCLEOPHILIC AROMATIC SUBSTITUTION OF AROMATIC CARBOXYLIC ACID DERIVATIVES SUPPORTING AT LEAST ONE ELECTRO-ATTRACTIVE GROUP
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Page/Page column 18-19, (2013/02/27)
Method for preparing carboxylic acid derivatives by aromatic nucleophilic substitution, in which a carboxylic acid derivative having a single carboxyl functional group, or one of the salts thereof, the carboxylic acid derivative having, in the ortho posit
Ortho-lithium/magnesium carboxylate-driven aromatic nucleophilic substitution reactions on unprotected naphthoic acids
Aissaoui, Regadia,Nourry, Arnaud,Coquel, Ariane,Dao, Thi Thanh Ha,Derdour, Aicha,Helesbeux, Jean-Jacques,Duval, Olivier,Castanet, Anne-Sophie,Mortier, Jacques
experimental part, p. 718 - 724 (2012/02/16)
Substitution of an ortho-fluoro or methoxy group in 1- and 2-naphthoic acids furnishing substituted naphthoic acids occurs in good to excellent yields upon reaction with alkyl/vinyl/aryl organolithium and Grignard reagents, in the absence of a metal catalyst without the need to protect the carboxyl (CO 2H) group. This novel nucleophilic aromatic substitution is presumed to proceed via a precoordination of the organometallic with the substrate, followed by an addition/elimination.
