- Cu-catalyzed intermolecular oxyalkylation of styrenes under air: Access to diverse iminolactones
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A practical, simple, and efficient copper-catalyzed highly regioselective oxyalkylation of styrenes and readily available α-bromoacetamides under air is realized. This reaction exhibits a wide range of functional group tolerance in styrenes and α-bromoacetamides to afford iminolactones.
- Lv, Yunhe,Pu, Weiya,Mao, Shukuan,Ren, Xiaoran,Wu, Yingtao,Cui, Hao
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- Erratum: Cu-Catalyzed Three-Component Carboamination of Alkenes (J. Am. Chem. Soc. (2018) 140:1 (58?61) DOI: 10.1021/jacs.7b10529)
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Pages 59 and 60. We have identified an error in the structural analysis of compounds presented in our publication detailing. (Table presented).
- Gockel, Samuel N.,Buchanan, Travis L.,Hull, Kami L.
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supporting information
p. 6019 - 6020
(2021/05/13)
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- Direct α-Tertiary Alkylations of Ketones in a Combined Copper–Organocatalyst System
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Herein, we report an efficient method for the tertiary alkylation of a ketone by using an α-bromocarbonyl compound as the tertiary alkyl source in a combined Cu-organocatalyst system. This dual catalyst system enables the addition of a tertiary alkyl radical to an enamine. Mechanistic studies revealed that the catalytically generated enamine is a key intermediate in the catalytic cycle. The developed method can be used to synthesize substituted 1,4-dicarbonyl compounds containing quaternary carbons bearing various alkyl chains.
- Kurose, Ayako,Ishida, Yuto,Hirata, Goki,Nishikata, Takashi
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supporting information
p. 10620 - 10625
(2021/04/09)
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- Catalytic Redox Chain Ring Opening of Lactones with Quinones to Synthesize Quinone-Containing Carboxylic Acids
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Catalytic ring opening of five- to eight-membered lactones with quinones is achieved through a redox chain mechanism. With low loading of a simple metal triflate Lewis acid catalyst and a chain initiator, C-H bonds of many quinones were efficiently functionalized with carboxylic acid-containing side chains. This method also features 100% atom economy and wide substrate scope. A novel route to the anti-asthma drug Seratrodast was developed. Mechanism study suggests that the redox chain reaction likely undergoes a carbocation intermediate.
- Xu, Xiao-Long,Li, Zhi
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p. 5078 - 5081
(2019/09/03)
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- Regioselective Synthesis of γ-Lactones by Iron-Catalyzed Radical Annulation of Alkenes with α-Halocarboxylic Acids and Their Derivatives
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An abundant and low toxicity iron catalyst has enabled regioselective annulation of alkenes with α-halocarboxylic acids and their derivatives. The reaction proceeds smoothly without any additional ligands, bases, and additives to afford a variety of γ-lactones in good yields. A proposed reaction pathway through radical annulation is supported by some mechanistic studies, involving radical clock and isotope labeling experiments. The present method was applied to the practical iron-powder-promoted synthesis of γ-lactones.
- Iwasaki, Masayuki,Miki, Natsumi,Ikemoto, Yuichi,Ura, Yasuyuki,Nishihara, Yasushi
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supporting information
p. 3848 - 3852
(2018/07/25)
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- Cu-Catalyzed Three-Component Carboamination of Alkenes
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Copper-catalyzed intermolecular carboamination of alkenes with α-halocarbonyls and amines is presented with 42 examples. Electron rich, electron poor, and internal styrenes, as well as α-olefins, are functionalized with α-halocarbonyls and aryl or aliphat
- Gockel, Samuel N.,Buchanan, Travis L.,Hull, Kami L.
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supporting information
p. 58 - 61
(2018/01/17)
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- Visible-Light-Induced C-O Bond Formation for the Construction of Five- and Six-Membered Cyclic Ethers and Lactones
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Visible-light-induced intramolecular C-O bond formation was developed using 2,4,6-triphenylpyrylium tetrafluoroborate (TPT), which allows the regiocontrolled construction of cyclic ethers and lactones. The reaction is likely to proceed through the single-electron oxidation of the phenyl group, followed by the formation of a benzylic radical, thus preventing a competing 1,5-hydrogen abstraction pathway. Detailed mechanistic studies suggest that molecular oxygen is used to trap the radical intermediate to form benzyl alcohol, which undergoes cyclization. This new approach serves as a powerful platform by providing efficient access to valuable five- and six-membered cyclic ethers and lactones with a unified protocol.
- Im, Honggu,Kang, Dahye,Choi, Soyeon,Shin, Sanghoon,Hong, Sungwoo
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supporting information
p. 7437 - 7441
(2018/11/27)
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- Copper-Catalyzed Oxidative Cyclization of Carboxylic Acids
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A method for converting C-H to C-O bonds through oxidative cyclization of carboxylic acids to generate lactone products is described. The reaction employs catalytic amounts of Cu(OAc)2 and potassium persulfate as the terminal oxidant and is performed open to air in an aqueous acetic acid solvent system. Preliminary mechanistic studies suggest that substrate oxidation likely proceeds by sulfate radical anion and that the Cu catalyst has no influence on the product-determining step. These conclusions differ from related investigations that propose the intermediacy of a carboxylate radical.
- Sathyamoorthi, Shyam,Du Bois
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supporting information
p. 6308 - 6311
(2016/12/23)
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- A catalytic approach to the metal-free reaction of epoxides with ketene silyl acetals for accessing γ-lactones
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The first catalytic approach to the nucleophilic addition of silyl ketene acetals 2 to epoxides 1 is reported. The defined protocol is metal-free using tetrabutylammonioum fluoride as the catalyst. It works in a very efficient manner under solvent-free co
- Bonollo, Simona,Ahmady, Amanollah Zarei,Petrucci, Chiara,Marrocchi, Assunta,Pizzo, Ferdinando,Vaccaro, Luigi
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supporting information
p. 5721 - 5723
(2015/02/19)
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- Formation of quaternary carbon centers by highly regioselective hydroformylation with catalytic amounts of a reversibly bound directing group
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Directly opposing Keulemans rule! Phosphinites work as reversibly bound directing groups allowing for the first highly regioselective hydroformylation of 3-substituted homoallylic alcohols to construct quaternary carbon centers. This method enables the at
- Ueki, Yusuke,Ito, Hideto,Usui, Ippei,Breit, Bernhard
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supporting information; experimental part
p. 8555 - 8558
(2011/09/19)
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- Lithium- α-lithioacetate and β-lithiopropionate: Useful intermediates in organic synthesis
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The reaction of chloroacetic acid and 3-chloropropionic acid with a base (LDA or Bu(n)Li, respectively) and then with an excess of lithium and a catalytic amount of 4,4'-di-tert-butylbiphenyl (DTBB, 5%) in the presence of different electrophiles [Bu'CHO, PhCHO, Et2CO, (CH2)5CO, PhCOMe] in THF at -78°C leads, after hydrolysis with water, to the expected hydroxy acids, which in the second case are directly cyclised under acidic conditions to give the expected γ-lactones. (C) 2000 Elsevier Science Ltd.
- Pastor, Isidro M.,Yus, Miguel
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p. 5335 - 5339
(2007/10/03)
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- Novel Type of the Favorskii Rearrangement Combined with Aldol Reaction Leading to γ-Butyrolactone Derivatives
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Reaction of aromatic aldehydes or hetero-aromatic aldehydes with 3-chloro-3-methyl-2-butanone in ethanolic KOH at room temperature gave 3,3-dimethyl-5-aryltetrahydro-2-furanone as a major product.The reaction can be tentatively explained by the combination of Favorskii rearrangement and aldol reaction.
- Sakai, Takashi,Yamawaki, Akitoshi,Katayama, Tsuyoshi,Okada, Hiroshi,Utaka, Masanori,Takeda, Akira
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p. 1067 - 1070
(2007/10/02)
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