- Nickel-Catalyzed Arylative Carboxylation of Alkynes with Arylmagnesium Reagents and Carbon Dioxide Leading to Trisubstituted Acrylic Acids
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Nickel-catalyzed arylcarboxylation of alkynes with arylmagnesium reagents and carbon dioxide (CO2, 1 atm) was realized in one pot. Various trisubstituted acrylic acids within an aryl group at the β-position have been prepared efficiently with good regioselectivity under mild conditions. The resulting products could be further transformed to benzoannelated cycles retaining CO2 as a one-carbon synthon.
- Wang, Sheng,Xi, Chanjuan
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supporting information
p. 4131 - 4134
(2018/07/15)
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- Synthesis of coumarins via PIDA/I2-mediated oxidative cyclization of substituted phenylacrylic acids
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A variety of functionalized coumarins were synthesized from substituted phenylacrylic acids via PIDA/I2-mediated and irradiation-promoted oxidative carbon-oxygen bond formation. Our studies show that the oxygen in the pendant carboxylic acid group cyclizes favorably to the aryl ring that is cis to it. The main advantages of this method include good functional group tolerance and the transition-metal-free characteristic. The Royal Society of Chemistry 2013.
- Li, Jinming,Chen, Huiyu,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
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p. 4311 - 4320
(2013/04/24)
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- Stereoselective olefination of unfunctionalized ketones via ynolates
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Ynolates react with ketones at room temperature to afford α,β,β,-trisubstituted acrylates (tetra-substituted olefins) with 2:1-8:1 geometrical selectivities. This can be regarded as a new olefination reaction of ketones giving tetrasubstituted olefins in good yield, even in the case of sterically hindered substrates. The reaction mechanism involves cycloaddition of ynolates with a carbonyl group and subsequent thermal electrocyclic ring-opening of the resulting β-lactone enolates. The stereoselectivity is determined in the ring-opening, which is regulated by torquoselectivity. In this paper, we describe the scope and limitations of olefination of ketones via ynolates and discuss the stereocontrol mechanism.
- Shindo, Mitsuru,Sato, Yusuke,Yoshikawa, Takashi,Koretsune, Ryoko,Shishido, Kozo
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p. 3912 - 3916
(2007/10/03)
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- Practical synthesis of ynolate anions: Naphthalene-catalyzed reductive lithiation of α,α-dibromo esters
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Reductive lithiation of α,α-dibromo esters using lithium naphthalenide afforded ester dianions leading to ynolate anions in good yields. Naphthalene-catalyzed reductive lithiation was also accomplished. This is a convenient, economical and practical method for the preparation of ynolate anions.
- Shindo, Mitsuru,Koretsune, Ryoko,Yokota, Wakako,Itoh, Kotaro,Shishido, Kozo
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p. 8357 - 8360
(2007/10/03)
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- Synthesis and biological evaluation of 3-(Prop-2-enyl)- and 3-(Prop-2-ynyl)pyrrolidine-2,5-dione derivatives as potential aromatase inhibitors
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3-(4'-Aminophenyl)pyrrolidine-2,5-dione (WSP3), a known reversible inhibitor of P450 aromatase, was modified using molecular graphics and our model of reversible inhibitor and substrate binding to resemble 10β-prop-2-ynylestr-4-ene-3,17-dione (PED), a mec
- Barrell,Woo,Ahmadi,Smith,Nicholls
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p. 154 - 159
(2007/10/03)
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- Ac2O/Et3N Induced Condensation of o-Hydroxybenzophenone with Phenylacetic Acid: A Study of the Mechanism of Coumarin Formation
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The mechanism of coumarin formation from o-hydroxybenzophenone and phenylacetic acid in the presence of Ac2O/Et3N has been investigated.Intermolecular hydrogen bonding of o-hydroxy leads to partial carbonium ion formation thereby facilitating nucleophilic
- Sharma, Indra,Ray, Suprabhat
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p. 374 - 375
(2007/10/02)
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