Categories: C-C Bond Formation > Arenes, Cyclic Compounds >
Synthesis of indanones
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Recent Literature
Cyclization of electron-rich 2-alkyl-1-ethynylbenzene derivatives was catalyzed
by TpRuPPh3(CH3CN)2PF6 in hot
toluene to form 1-substituted-1H-indene and 1-indanone products. The
cyclization mechanism involves a 1,5-hydrogen shift of an initial
metal-vinylidene intermediate.
A. Odedra, S. Datta, R.-S. Liu, J. Org. Chem., 2007,
72, 3289-3292.
A catalytic amount of SbF5 efficiently converted a mixture of
phenylalkynes and aldehydes to indanone compounds in one pot in the presence of
EtOH as an additive, and the reaction afforded the corresponding
2,3-disubstituted indanones as a single trans-isomer.
A. Saito, M. Umakoshi, N. Yagyu, Y. Hanzawa, Org. Lett., 2008,
10, 1783-1785.
Indanones and 2-cyclopentenones have been successfully prepared in good to
excellent yields by the palladium-catalyzed carbonylative cyclization of
unsaturated aryl iodides and dienyl triflates, iodides, and bromides,
respectively. The mechanism is discussed.
S. V. Gagnier, R. C. Larock, J. Am. Chem. Soc., 2003,
125, 4804-4807.
The preparation of indanones by the intramolecular acylation of 3-arylpropanoic
acids or halides requires the use of noncatalytic acid promoters. In the
presence of a catalytic amount FeCl3, in situ generated dimethyl
acetals of (E)-2-alkylcinnamaldehydes cyclize to 1-methoxy-2-alkyl-1H-indenes
in good-to-high yields. The 1-methoxyindenes were converted in high yield into
2-alkylindanones.
G. B. Womack, J. G. Angeles, V. E. Fanelli, C. A. Heyer, J. Org. Chem.,
2007,
72, 7046-7049.
A new palladium(0)-catalyzed three-component reaction of salicylic aldehyde
triflates, ethylene glycol vinyl ether, and various secondary nucleophilic
amines involving an initial internal Heck arylation, iminium ion formation, and
subsequent tandem cyclization gives tertiary 3-aminoindan acetals.
A. Arefalk, M. Larhed, A. Hallberg, J. Org. Chem., 2005, 70,
938-942.
