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Published on: January 19, 2016
Preparations of SF(5)- and CF(3)-substituted arenes utilizing the 7-oxabicyclo[2.2.1]hept-2-ene synthones
Maxim V Ponomarenko1, Katrin Lummer, Andrey A Fokin
1School of Engineering and Science, Jacobs University Bremen gGmbH, Campus Ring 1, 28759 Bremen, Germany. m.ponomarenko@jacobs-university.de.
Abstract:
The synthesis of SF5- and CF3-substituted benzenes and naphthalenes from various 7-oxanorbornene derivatives utilizing SF5Cl and CF3I radical addition reactions, followed by dehydrohalogenation and aromatization, is reported. The differences in the behavior of the SF5- and CF3-containing intermediates under basic and acidic conditions are discussed. The experimentally observed high regioselectivities of the formation of 2-RF-substituted-1-naphthols agree well with the ab initio computations, revealing the first example of the SF5···HO hydrogen bonding.
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