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Categories: C-C Bond Formation > Arenes, Cyclic Compounds > Benzocycloalkenones

Synthesis of tetralones

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1,1,1,3,3,3-hexafluoro-2-propanol promotes an intramolecular Friedel-Crafts acylation of a broad range of arylalkyl acid chlorides without additional catalysts or reagents. This reaction is operationally trivial.
H. F. Motiwala, R. H. Vekariya, J. Aubé, Org. Lett., 2015, 17, 5484-5487.


A catalyst generated in situ from [Rh(COD)Cl]2, (R)-DTBM-SEGPHOS, and NaBARF promotes an endo- and enantioselective hydroacylation of ortho-allylbenzaldehydes. These rhodium-catalyzed processes generate the 3,4-dihydronaphthalen-1(2H)-one products in good yields with excellent enantioselectivities with minimal formation of byproducts from competitive alkene isomerization and ene/dehydration pathways.
K. F. Johnson, A. C. Schmidt, L. M. Stanley, Org. Lett., 2015, 17, 4654-4657.


Brønsted acid-mediated cyclizations of siloxyalkynes with simple arenes and alkenes afforded substituted tetralone and cyclohexenone derivatives. A wide range of substrates can be employed in these carbocyclizations.
L. Zhang, S. A. Kozmin, J. Am. Chem. Soc., 2004, 126, 10204-10205.