2009
DOI: 10.1016/j.tetlet.2009.02.191
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Synthesis of acenes via coupling of 1,4-dilithiobutadienes with diiodoarenes in the presence of CuCl

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Cited by 32 publications
(10 citation statements)
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“…Considering that 1,4‐M 2 can be readily prepared from the corresponding 1,4‐X 2 and, in particular, the structural variation of available 1,2‐X 2 is much broader than that of 1,2‐M 2 : thus mode B‐type annulation could greatly expand the repertoire of accessible PAHs. However, the precedents of mode B‐type annulation were limited to only the reactions of 2,2′‐diborylbiphenyls,4a zirconacyclopentadienes,4bd [Zr(2,2′‐biphenyldilyl) 3 ][Li⋅(THF) 4 ] 2 ,4eg 2,2′‐distannylbinaphthyl,4h and 1,4‐dilithiobutadienes4j with 1,2‐dihalobenzenes, and there is still much room for improvement in the scope of the substrates and reagents, yields, and reaction conditions.…”
Section: Methodsmentioning
confidence: 99%
“…Considering that 1,4‐M 2 can be readily prepared from the corresponding 1,4‐X 2 and, in particular, the structural variation of available 1,2‐X 2 is much broader than that of 1,2‐M 2 : thus mode B‐type annulation could greatly expand the repertoire of accessible PAHs. However, the precedents of mode B‐type annulation were limited to only the reactions of 2,2′‐diborylbiphenyls,4a zirconacyclopentadienes,4bd [Zr(2,2′‐biphenyldilyl) 3 ][Li⋅(THF) 4 ] 2 ,4eg 2,2′‐distannylbinaphthyl,4h and 1,4‐dilithiobutadienes4j with 1,2‐dihalobenzenes, and there is still much room for improvement in the scope of the substrates and reagents, yields, and reaction conditions.…”
Section: Methodsmentioning
confidence: 99%
“…Thus, the cycloaddition of 45 with electron‐deficient alkynes or alkenes has been applied to the synthesis of functionalized dihydroacenes of type 46 , which can be converted either into the corresponding acenes 47 by dehydrogenation or into larger hydroacene derivatives through an iterative sequence (Scheme ) . Moreover, the iodination/lithiation of 45 gives rise to 1,4‐dilithiobutadienes 49 , which can be coupled with diiodoarenes in the presence of CuCl to afford dihydroacenes of type 50 …”
Section: Acenes From Hydroacenesmentioning
confidence: 99%
“…Accordingly, the chemists continue to devise new synthetic methods to efficiently construct these structural motifs. Among various synthetic routes to π-conjugated naphthalenes, homologation of mono- or difunctionalized arenes have attracted much attention. Cyclotrimerization of arynes, benzannulation of biaryls, and cyclization of certain diarylethenes are developed synthetic strategies to phenanthrenes as well .…”
mentioning
confidence: 99%