一个小前驱体的偶联和裂解一步生成脱取代菲

IF 2.7 3区化学 Q2 CHEMISTRY, ORGANIC European Journal of Organic Chemistry Pub Date : 2025-02-11 DOI:10.1002/ejoc.202401326

Ki F. Finch, Prof. Dr. Alex McSkimming, Dr. Xiaodong Zhang, Dr. Qi Zhao, Mingshu Xie, Prof. Dr. Robert A. Pascal Jr.

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引用次数: 0

摘要

当8 -溴- 1,2,3,4,5,6,7 -庚苯基- 1,4 -二氢- 1,4 -环氧萘(5)与铜粉在340℃氩气下加热时，主要产物为1,8 -二苯甲酰- 2,3,4,5,6,7,9,10 -八苯基菲(6)，收率高达68%。该反应似乎涉及5的乌尔曼偶联和两分子二苯乙炔的排出，得到一个十苯基二（异苯并呋喃），然后经历分子内环化和裂解，产生菲6。

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One-Step Formation of a Decasubstituted Phenanthrene by Coupling and Fragmentation of a Smaller Precursor

When 8-bromo-1,2,3,4,5,6,7-heptaphenyl-1,4-dihydro-1,4-epoxynaphthalene (5) is heated with copper powder and no solvent at 340 °C under argon, the chief product is 1,8-dibenzoyl-2,3,4,5,6,7,9,10-octaphenylphenanthrene (6) in yields as high as 68 %. The reaction appears to involve Ullmann coupling of 5 and expulsion of two molecules of diphenylacetylene to give a decaphenyl bis(isobenzofuran) which then undergoes intramolecular cyclization and fragmentation to yield phenanthrene 6.

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来源期刊

European Journal of Organic Chemistry 化学-有机化学

CiteScore

5.40

自引率

3.60%

发文量

752

审稿时长

1 months

期刊介绍： The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.