38858-73-0Relevant academic research and scientific papers
Trialkylaluminum-Alkylidene Iodide. A Powerful Cyclopropanation Agent with Unique Selectivity
Maruoka, Keiji,Fukutani, Yoshimi,Yamamoto, Hisashi
, p. 4412 - 4414 (1985)
A highly convenient and versatile method for the synthesis of cyclopropanes has been described which involves treatment of olefins with a variety of trialkylaluminiums and alkylidene iodide under mild conditions.
Iron-Catalyzed Ring-Opening Reactions of Cyclopropanols with Alkenes and TBHP: Synthesis of 5-Oxo Peroxides
Lou, Chenhao,Wang, Xin,Lv, Leiyang,Li, Zhiping
supporting information, p. 7608 - 7612 (2021/10/02)
The ring opening of cyclopropanols is rarely used in multicomponent reactions. Herein we report the three-component reaction of cyclopropanols with alkenes and tert-butyl hydroperoxide (TBHP) catalyzed by an iron catalyst. This protocol enables the incorporation of both the β-carbonyl fragment and a peroxy unit across the C=C double bond regioselectively, thus allowing an efficient, facile access to 5-oxo peroxides. Modification of the biologically active molecules and various downstream derivatizations of the peroxides are also demonstrated.
Aryl Pyrazoles from Photocatalytic Cycloadditions of Arenediazonium
Cardinale, Luana,Neumeier, Michael,Majek, Michal,Jacobi Von Wangelin, Axel
supporting information, p. 7219 - 7224 (2020/10/02)
A photocatalytic synthesis of 1,5-diaryl pyrazoles from arenediazoniums and arylcyclopropanols is reported. The reaction proceeded under mild conditions (rt, 20 min) with catalytic [Ru(bpy)3]2+ under blue-light irradiation and exhibited compatibility with several functional groups (e.g., I, SF5, SO2NH2, N3, CN) and perfect levels of regiocontrol. Mechanistic studies (luminescence spectroscopy, CV, DFT, radical trapping, quantum yield determination) documented an initial oxidative quenching of the excited photocatalyst and the operation of a radical-chain mechanism.
Visible-Light-Induced Alkoxyl Radical Generation Enables Selective C(sp3)-C(sp3) Bond Cleavage and Functionalizations
Jia, Kunfang,Zhang, Fuyuan,Huang, Hanchu,Chen, Yiyun
supporting information, p. 1514 - 1517 (2016/02/20)
The alkoxyl radical is an important reactive intermediate in mechanistic studies and organic synthesis; however, its current generation from alcohol oxidation heavily relies on transition metal activation under strong oxidative conditions. Here we report the first visible-light-induced alcohol oxidation to generate alkoxyl radicals by cyclic iodine(III) reagent catalysis under mild reaction conditions. The β-fragmentation of alkoxyl radicals enables selective C(sp3)-C(sp3) bond cleavage and alkynylation/alkenylation reactions with various strained cycloalkanols, and for the first time with linear alcohols.
Iron- or silver-catalyzed oxidative fluorination of cyclopropanols for the synthesis of β-fluoroketones
Ren, Shichao,Feng, Chao,Loh, Teck-Peng
supporting information, p. 5105 - 5109 (2015/05/13)
The FeIII- or AgI-catalyzed oxidative fluorination of cyclopropanols via radical rearrangement is disclosed. This process features a straightforward and highly effective protocol for the site-specific synthesis of β-fluoroketones and represents an expedient method for the synthesis of γ-, δ- and ε-fluoroketones. Notably, this reaction proceeds at room temperature and tolerates a diverse array of cyclopropanols.
Stereospecific construction of chiral tertiary and quaternary carbon by nucleophilic cyclopropanation with bis(iodozincio)methane
Nomura, Kenichi,Matsubara, Seijiro
supporting information; experimental part, p. 147 - 152 (2010/04/23)
The reaction of a ketone having a leaving group at the aposition, such as a,bepoxy ketone or asulfonyloxy ketone, with bis(iodozincio) methane affords a zinc alkoxide of cyclopropanol. The reaction proceeds by nucleophilic addition of the dizinc to the carbonyl group and a sequential intramolecular nucleophilic substitution of the introduced iodozinciomethyl group to the adjacent electrophilic carbon that has a leaving group. When an optically active a,β-epoxy ketone or asulfonyloxy ketone is treated with the dizinc, a zinc alkoxide of cyclopropanol having a chiral tertiary or quaternary carbon in the cyclopropane ring is obtained, and the obtained zinc alkoxide of cyclopropanol acts as a chiral ho-moenolate. When it is treated with an electrophile in the presence of copper cyanide, it gives an optically active a-tertiary or -quaternary ketone that retains high optical purity.
Allylic fluorides via the cleavage of tertiary cyclopropyl silyl ethers with diethylaminosulfur trifluoride
Kirihara, Masayuki,Kambayashi, Toshihiro,Momose, Takefumi
, p. 1103 - 1104 (2007/10/03)
Treatment of tertiary cyclopropyl silyl ethers with diethylaminosulfur trifluoride (DAST) causes ring opening to give allylic fluorides in moderate to high yields.
A facile cyclopropanol synthesis from β-halo ester with Grignard reagent-samarium(II) diiodide couple
Fukuzawa,Niimoto,Sakai
, p. 7691 - 7694 (2007/10/02)
Transformation of α,β-halo ester to the cyclopropanols by a coupled reagent of samarium(II) diiodide with Grignard reagent in tetrahydrofuran-hexamethylphosphoric triamide was very successful under mild conditions.
Reaction of Enol Ethers with Zinc Carbenoid Reagents. Cyclopropanation and Subsequent Isomerization to Allylic Ethers
Ryu, Ilhyong,Aya, Tomoyuki,Otani, Shoji,Murai, Shinji,Sonoda, Noboru
, p. 279 - 290 (2007/10/02)
The reactions of enol ethers (ROC=C, R= alkyl, silyl) with zinc carbenoid reagents were found to give allylic ethers in several cases along with the expected cyclopropyl etehrs.The ratio of these two products was highly dependent on the concentration of t
