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

Synthesis of tetralones


Recent Literature

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.

The organic photocatalyst 4CzIPN, visible light, and N-(acyloxy)phthalimides as radical precursors enable an intramolecular arene alkylation reaction. This reaction provides a diverse set of fused, partially saturated cores which are of high interest in synthetic and medicinal chemistry.
T. C. Sherwood, H.-Y. Xiao, R. G. Bhaskar, E. M. Simmons, S. Zaretsky, M. P. Rauch, R. R. Knowles, T. G. M. Dhar, J. Org. Chem., 2019, 84, 8360-8379.

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.

A CuI·SMe2-mediated homoconjugate addition followed by a decarboxylative Dieckmann cyclization provides arene-fused cyclic β-ketoesters from 2-iodoaryl esters and 1,1-cyclopropane diesters. Various iodoaryl esters and 1,1-cyclopropane diesters were evaluated, and the limitations of both reactions are discussed.
Z. Chen, A. Y. Hong, X. Linhu, J. Org. Chem., 2018, 83, 6225-6234.

Enantioenriched CN-containing all-carbon quaternary stereocenters can be assembled by desymmetrizing cyclization of aryl/alkenyl halide-tethered malononitriles. The use of a silane reductant is crucial to the enantioselectivity and reactivity.
Z.-H. Chen, R.-Z. Sun, F. Yao, X.-D. Hu, L.-X. Xiang, H. Cong, W.-B. Liu, J. Am. Chem. Soc., 2022, 144, 4776-4782.

A proton-coupled electron transfer mediated by an organic photoredox catalyst enables a metal-free ring expansion of cyclopropanols containing a pendant styrene moiety to provide 1-tetralone and 1-benzosuberone derivatives depending on the substitution pattern of the alkene moiety.
T. Kikuchi, K. Yamada, T. Yasui, Y. Yamaoto, Org. Lett., 2021, 23, 4710-4714.