Efficient Synthesis of Symmetrical 2,5-Disubstituted Benzoquinones via Palladium-Catalyzed Double Negishi Coupling

Journal of Organic Chemistry

Volumn 63, Issue 11, 1998, Pages 3764-3768

  Palmgren, Andreas ^a   Thorarensen, Atli ^a   Bäckvall, Jan E ^a,b  

^a UPPSALA UNIVERSITY   (Sweden)

^b STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000568291     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9721812     Document Type: Article

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37. 13 for the 1,4-oxidation of 2-phenyl-1,3-cyclohexadiene (7) afforded 3,6-diacetoxy-1-phenylcyclohexane (8) in moderate yield (43%) with a cis/trans ratio of 86/14. Disappointingly, the cis and the trans product were obtained as racemates. The interesting observation is that the cis/trans selectivity (86/14) is reversed compared to any previously employed ligands in the reaction under chloride-free conditions (see: Grennberg, H.; Langer, V.; Bäckvall, J. E. J. Chem. Soc., Chem. Commun. 1991, 1190). This high cis selectivity in the oxidation indicates a bis-chelation of the ligand to palladium during the activation of the π-allyl complex. The bis-coordination prevents coordination of acetate to palladium, and as a result, mainly external attack by acetate occurs, affording the cis-product.
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