Categories: C-C Bond Formation > Arenes, Cyclic Compounds > Benzocycloalkenes
Synthesis of benzocyclohexenes (tetrahydronaphthalenes)
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Recent Literature
Copper-catalyzed cascade reactions between alkenes or alkynes and diaryliodonium
salts form carbocyclic products. The reactions proceed via arylation of the
unsaturated functional group, formation of a carbocation intermediate that
facilitates hydride shift pathways to translocate the positive charge to a
remote position, and Friedel-Crafts-type ring formation.
F. Zhang, S. Das, A. J. Wlkinshaw, A. Casitas, M. Taylor, M. G. Suero, M. J.
Gaunt, J. Am. Chem. Soc., 2014,
136, 8851-8854.
An intramolecular, Pd-catalyzed C-H alkylation of arenes and heteroarenes is
successful with various unactivated primary and secondary alkyl halides,
including those with β-hydrogens. The mild, catalytic reaction conditions are
highly functional group tolerant and facilitate access to a broad range of
synthetically and medicinally interesting carbocyclic and heterocyclic systems.
A. R. O. Venning, P. T. Bohan, E. J. Alexanian, J. Am. Chem. Soc., 2015,
137, 3731-3734.
Re2O7 or HReO4 catalyze highly efficient
intramolecular hydroarylations of styrene derivatives for the facile synthesis
of substituted 1-aryltetralin structures. This method is characterized by mild
reaction conditions, broad substrate scope, high chemical yields, and high atom
economy. An efficient total synthesis of an isoCA-4 analogue is described.
R. Gul, L. Hu, Y. Liu, Y. Xie, J. Org. Chem., 2023, 88,
12079-12086.
2-[(Trimethylsilyl)methyl]benzyl methanesulfonates give o-quinodimethanes
in the presence of potassium fluoride and a catalytic amount of 18-crown-6 at
room temperature. A subsequent reaction with electron-deficient olefins affords
[4+2] cycloadducts in good yields.
H. Shirakawa, H. Sano, Synthesis, 2014, 46,
1788-1792.
An operational simple iron(III)-catalyzed strategy toward functionalized
tetrahydronaphthalenes in high yields takes advantage of a unique reactivity
observed for simple aryl ketone precursors . Detailed mechanistic investigations
identified pyrans as reactive intermediates that afford the desired
tetrahydronaphthalenes upon iron(III)-catalyzed Friedel-Crafts alkylation.
R. B. Watson, C. S. Schindler Org. Lett.,
2018, 20, 68-71.
An oxetane intermediate during a direct aldol reaction can be trapped with an
internal aryl group to yield trans-tetraline products.
T. Kuri, Y. Mizukami, M. Shimogaki, M. Fujita,
Org. Lett., 2020, 22, 7613-7616.
A cationic rhodium(I)/BINAP complex-catalyzed decarboxylative [2 + 2 + 2]
cycloaddition of 1,6- and 1,7-diynes with commercially available vinylene
carbonate enables a new route to substituted phenols.
H. Hara, M. Hirano, K. Tanaka, Org. Lett., 2009,
11, 1337-1340.
A ligand-enabled nickel-catalyzed intramolecular hydroalkenylation of imines
with unactivated alkenes provides various five- and six-membered cyclic allylic
amines in high yields. The use of both wide-bite-angle diphosphine ligand and
Brønsted acid is crucial for realizing the reaction.
W.-M. Feng, T.-Y. Li, L.-J. Xiao, Q.-L. Zhou, Org. Lett., 2021, 23,
7900-7904.
Benzyne-[2+2] cycloadditions with enamides enabled the development of a
highly stereoselective tandem [2+2] cycloaddition-pericyclic
ring-opening-intramolecular-N-tethered-[4+2] cycloaddition for rapid
assembly of nitrogen heterocycles.
J. B. Feltenberge, R. Hayashi, Y. Tang, E. S. C. Babiash, R. P. Hsung, Org. Lett., 2009,
11, 3666-3669.