PMID: 11312967Apr 21, 2001Paper

Copper(II)-mediated oxidative coupling of 2-aminonaphthalene homologues. Competition between the straight dimerization and the formation of carbazoles

The Journal of Organic Chemistry
S VyskocilP Kocovský

Abstract

Whereas the Cu(II)-mediated oxidative coupling of 2-aminonaphthalenes 7a and 7b results in the clean formation of 1,1'-binaphthyls 13a and 13b, respectively, their higher homologues and congeners 8-12 have been found to exhibit a different reaction pattern. Thus, 2-aminoanthracene (8) gave a approximately 1:1 mixture of the expected bianthryl derivative 15 and the carbazole 16, whereas the 9-aminophenanthrene (10), 3-phenyl-1-aminonaphthalene (11), and 2-aminochrysene (12) produced almost exclusively the corresponding carbazoles 19, 20, and 21, respectively. By contrast, the isomeric 3-aminophenanthrene (9) gave rise to the azo compound 17 as a result of the preferential oxidation on the nitrogen. The carbazoles have been shown to arise directly from the coupling reactions rather than from the primarily formed binaphthyls. Alternatively, carbazole 19 can also be prepared from 1b on reaction with hydrazine. On the other hand, treatment of 3a with hydrazine resulted in the formation of a approximately 2:7 mixture of amine 11 and arylhydrazine 22. 2,2'-Diamino-1,1'-bianthryl (15) has been resolved into enantiomers via cocrystallization with (-)-N-benzylcinchonidinium chloride and shown to have (R)-(-)-15 configuration by X-ray cry...Continue Reading

References

Jan 1, 1995·Acta Crystallographica. Section A, Foundations of Crystallography·R H Blessing
Oct 25, 2001·The Journal of Organic Chemistry·Scott E. DenmarkJun Young Choi

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Citations

Jun 22, 2013·Chemical Reviews·Scott E AllenMarisa C Kozlowski
Nov 7, 2008·Chemistry : a European Journal·Louis AdriaenssensFilip Teplý
Apr 25, 2019·Chemistry, an Asian Journal·Satoru Hiroto
Sep 12, 2012·Angewandte Chemie·Kiyohiko GotoHiroshi Shinokubo
Nov 2, 2018·Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan·Kenji Matsumoto
May 16, 2019·Organic & Biomolecular Chemistry·Jan OtevrelPavel Bobal
Mar 26, 2010·Organic Letters·Ameneh TatarBohumil Dolenský
Aug 14, 2003·Chemical Reviews·Pavel KocovskýMartin Smrcina
Apr 3, 2018·Organic Letters·Hagit ForkoshDoron Pappo
Nov 11, 2011·The Journal of Organic Chemistry·Malapaka ChandrasekharamB Sridhar
Sep 23, 2014·Organic Letters·Kenji MatsumotoMitsuru Shindo

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