Categories: C-C Bond Formation > Arenes, Cyclic Compounds >
Synthesis of indenones
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Recent Literature
In the presence of a rhodium catalyst, paraformaldehyde enables a CO gas-free
carbonylative cyclization of alkynes with 2-bromophenylboronic acids to yield
indenone derivatives. Rhodium-catalyzed decarbonylation of formaldehyde is
followed by carbonylation of alkynes with 2-haloboronic acids, respectively,
leading to efficient whole carbonylation.
T. Morimoto, K. Yamasaki, A. Hirano, K. Tsutusmi, N. Kagawa, K. Kakiuchi, Y.
Harada, Y. Fukukomoto, N. Chatani, T. Nishioka, Org. Lett., 2009,
11, 1777-1780.
An iron-promoted oxidative tandem alkylation/cyclization of ynones with
4-alkyl-substituted 1,4-dihydropyridines provides 2-alkylated indenones with
excellent selectivity under mild conditions. The process occurs via oxidative
homolysis of a C-C σ-bond in 1,4-dihydropyridines to generate an alkyl radical
followed by its addition to the C-C triple bond and an intramolecular
cyclization.
F.-T. Xiong, B.-H. He, Y. Liu, Q. Zhou, J.-H. Fan, J. Org. Chem., 2022, 87,
8599-8610.
An efficient gold-catalyzed cyclization of 2-alkynylaldehyde cyclic acetals
enables the synthesis of or a braod range of indenone derivatives in very good
yields. The cyclic acetal group promotes a 1,5-H shift by activating the
benzylic C-H bond and preventing the migration of the alkoxy group by tethering
both alkoxy groups.
T. Yamada, K. Park, T. Tachikawa, A. Fujii, M. Rudoplf, A. S. K. Hashmi, H.
Sajiki,
Org. Lett., 2020, 22, 1883-1888.
A facile, efficient, and large-scale strategy for the synthesis of N-(1-Oxo-1H-inden-2-yl)benzamide
derivatives via domino reaction between aryl aldehydes, hippuric acid, and
acetic anhydride is catalyzed by HPW@nano-SiO2 under microwave
irradiation. The reaction conditions are very simple and offer convenient
isolation of the product. Moreover, the catalyst can be re-used up to five times
after simple filtration.
M. Rostami, A. R. Khosropour, V. Mirkhani, I. Mohammadpoor-Baltork, M. Moghadam,
S. Tangestaninejad, Synlett, 2011,
1677-1682.
An efficient rhodium-catalyzed C-H activation and multistep cascade reaction of
benzimidates and alkenes enables the synthesis of diverse difunctionalized
indenones in the presence of Mn(OAc)2. The transformation involves
the cleavage and formation of multiple bonds in one pot under mild reaction
conditions.
N. Lv, Z. Chen, Y. Liu, Z. Liu, Y. Zhang, Org. Lett.,
2017, 19, 2588-2591.
One-pot tandem Meyer-Schuster rearrangement of arylpropynols and successive
radical cyclization with disulfides enables the synthesis of 2-sulfenylindenone
derivatives in good yields. The reaction tolerates a number of functional groups.
X.-S. Zhang, J.-Y. Jiao, X.-H. Zhang, B.-L. Hu, X.-G. Zhang, J. Org. Chem.,
2016,
81, 5710-5716.
An electrooxidative direct arylsulfonlylation of ynones with sulfinic acids via
a radical tandem cyclization strategy enables the construction of sulfonated
indenones under oxidant-free conditions in very good yields. Notably, this
reaction could be easily scaled up with good efficiency.
J. Wen, W. Shi, F. Zhang, D. Liu, S. Tang, H. Wang, X.-M. Lin, A. Lei, Org. Lett.,
2017, 19, 3131-3134.