- Iron-Catalyzed Ring Expansion of Cyclobutanols for the Synthesis of 1-Pyrrolines by Using MsONH3OTf
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The synthesis of 1-pyrrolines from cyclobutanol derivatives and an aminating reagent (MsONH3OTf) has been developed. This one-pot procedure achieves C–N bond/C═N bond formation via ring expansion. A series of 1-pyrroline derivatives are synthes
- Zhuang, Daijiao,Gatera, Tharcisse,An, Zhenyu,Yan, Rulong
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supporting information
p. 771 - 775
(2022/01/20)
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- Nickel-Catalyzed Favorskii-Type Rearrangement of Cyclobutanone Oxime Esters to Cyclopropanecarbonitriles
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A nickel-catalyzed base-promoted rearrangement of cyclobutanone oxime esters to cyclopropanecarbonitriles was developed. The ring opening of cyclobutanone oxime esters occurs at the sterically less hindered side. A base-promoted nickelacyclobutane intermediate, formed in situ, is assumed to be involved in the formation of the product.
- Fang, Ping,Mei, Tian-Sheng,Shuai, Bin
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supporting information
p. 1637 - 1641
(2021/10/02)
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- Rhodium-Catalyzed Ring-Opening Hydroacylation of Alkylidenecyclopropanes with Chelating Aldehydes for the Synthesis of γ,δ-Unsaturated Ketones
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The first intermolecular ring-opening hydroacylation of alkylidenecyclopropanes with chelating aldehydes through a rhodium-catalyzed acrylamide-promoted protocol is reported. This highly efficient catalytic system enables the direct synthesis of a diverse
- Li, Hong-Shuang,Lu, Shi-Chao,Chang, Zhi-Xin,Hao, Liqiang,Li, Fu-Rong,Xia, Chengcai
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supporting information
p. 5145 - 5150
(2020/07/04)
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- Transition Metal-Free Difunctionalization of C?C Bond with Sodium Sulfinates and Water Leading to (E)-1-Phenyl-4-sulfonylbut-1-enes
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Without using any transitionmetal and base, an eco-friendly, practical and economical protocol has been established for the one-pot synthesis of diverse (E)-1-phenyl-4-sulfonylbut-1-enes from easily accessible starting materials. This strategy features a wide substrate scope, tolerates a broad range of functional groups, employs a less expensive oxidant, is operationally simple, and can be easily scaled-up. (Figure presented.).
- Wang, Qiao-Lin,Chen, Zan,Zhou, Quan,Zhou, Cong-Shan,Xiong, Bi-Quan,Zhang, Pan-Liang,Yang, Chang-An,Liu, Yu,Tang, Ke-Wen
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supporting information
p. 2315 - 2320
(2019/04/13)
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- Visible-Light-Catalyzed C-C Bond Difunctionalization of Methylenecyclopropanes with Sulfonyl Chlorides for the Synthesis of 3-Sulfonyl-1,2-dihydronaphthalenes
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A novel visible-light-catalyzed sulfonylation/arylation of carbon-carbon σ-bond with sulfonyl chlorides for the synthesis of 3-sulfonylated 1,2-dihydronaphthalenes is developed. This difunctionalization proceeds via a sequence of C=C bond sulfonylation, C-C σ-bond cleavage, and intramolecular cyclization, and the experiment result shows that the C-C σ-bond difunctionalization reaction includes a radical process. This strategy provides a simple and convenient route for difunctionalization of C-C bonds with an aromatic carbon and a sulfonyl radical by one-pot construction of a C-S bond and a new C-C bond.
- Liu, Yu,Wang, Qiao-Lin,Chen, Zan,Zhou, Quan,Li, Hua,Zhou, Cong-Shan,Xiong, Bi-Quan,Zhang, Pan-Liang,Tang, Ke-Wen
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p. 2829 - 2839
(2019/03/07)
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- Visible light-induced palladium-catalyzed ring opening β-H elimination and addition of cyclobutanone oxime esters
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A palladium catalyst under visible light irradiation activates cyclobutanone oxime ester through single electron transfer to induce radical ring opening to generate hybrid cyanoalkyl Pd(i) radical species. Hybrid cyanoalkyl Pd(i) radical species can undergo either β-H elimination to deliver (E)-4-arylbut-3-enenitrile or undergo radical addition with silyl enol ether and enamide to generate δ-cyano ketones. A dual ligand system composed of two phosphine ligands is essential for the high reactivity.
- Xing, Wei-Long,Shang, Rui,Wang, Guang-Zu,Fu, Yao
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supporting information
p. 14291 - 14294
(2019/12/02)
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- Cu-Catalyzed Redox-Neutral Ring Cleavage of Cycloketone O-Acyl Oximes: Chemodivergent Access to Distal Oxygenated Nitriles
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A chemodivergent copper-catalyzed ring opening of cycloketone oximes via radical-mediated C-C bond cleavage under redox-neutral conditions is described. This method allows the divergent synthesis of γ- and δ-acyloxylated, alkoxylated, and hydroxylated nitriles while avoiding the use of toxic cyanide reagents. Moreover, these reactions proceed under very mild conditions with good functional group tolerance. Notably, ring-opening reactions of the less-strained substrate cyclopentanone oxime also proceeded well under the established conditions.
- Ai, Wenying,Liu, Yaqian,Wang, Qian,Lu, Zhonglin,Liu, Qiang
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supporting information
p. 409 - 412
(2018/01/27)
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- Synthesis of Spiro[2.2]pentanes and Spiro[2.3]hexanes Employing the Me3Al/CH2I2 Reagent
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Substituted alkylidenecyclopropanes reacted with 5 equivalents each of Me3Al and CH2I2 at room temperature in hexane to give 1-mono- and 1,1-disubstituted spiro[2.2]pentanes in high yields. Surprisingly, the same reaction
- Ramazanov, Ilfir R.,Kadikova, Rita N.,Zosim, Tat'yana P.,Dzhemilev, Usein M.,de Meijere, Armin
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p. 7060 - 7067
(2017/12/28)
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- Difluoroalkylation/C-H Annulation Cascade Reaction Induced by Visible-Light Photoredox Catalysis
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We report the first example of difluoroalkylation/C-H annulation cascade reactions of cyclopropyl olefins induced by visible-light photoredox catalysis regioselectively affording partially hydrogenated naphthalenes and quinolines with a variety of difluorinated side chains. The alkylation reagent could be extended to monofluoro and trifluoro reagents, nitrile and malonate. The regioselectivity was investigated by means of density functional theory calculations.
- Li, Jin,Chen, Jingzhi,Jiao, Wei,Wang, Guoqiang,Li, Ying,Cheng, Xu,Li, Guigen
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p. 9992 - 10001
(2016/10/31)
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- Copper(I)-Catalyzed Intramolecular Trifluoromethylation of Methylenecyclopropanes
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Copper(I)-catalyzed intramolecular trifluoromethylation of methylenecyclopropanes has been developed to produce a variety of CF3-substituted dihydronaphthalenes in moderate to good yields, relying on the construction of C(sp2)-CFsub
- Zhu, Zi-Zhong,Chen, Kai,Yu, Liu-Zhu,Tang, Xiang-Ying,Shi, Min
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supporting information
p. 5994 - 5997
(2016/01/09)
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- Synthesis of benzylidenecyclopropanes from γ-halopropyl pentachlorophenyl sulfones using a Julia-Kocienski olefination
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Simple, one-step synthesis of benzylidenecyclopropanes from γ-halopropyl pentachlorophenyl sulfones using a Julia-Kocienski olefination is reported. Georg Thieme Verlag Stuttgart.
- Ma?kosza, Mieczys?aw,Bujok, Robert
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p. 586 - 588
(2008/12/22)
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- Enantioselective synthesis of γ-aryl-γ-butyrolactones by sequential asymmetric epoxidation, ring expansion, and Baeyer-Villiger oxidation
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(Chemical Equation Presented) This paper describes an enantioselective synthesis of γ-butyrolactones, using the N-tolyl-substituted oxazolidinone-containing ketone as catalyst and Oxone as oxidant via a sequential asymmetric epoxidation of benzylidenecyclopropanes, ring expansion, and Baeyer-Villiger oxidation. Up to 91% ee was obtained. Optically active cyclobutanones can also be obtained by suppressing the Baeyer-Villiger oxidation with use of more ketone catalyst and less Oxone.
- Wang, Bin,Shen, Yu-Mei,Shi, Yian
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p. 9519 - 9521
(2007/10/03)
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- A General Procedure for Preparing α-Lithiosilanes. Generalization of the Peterson Olefination
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A particularly convenient method for the preparation of α-lithiosilanes consists of the reductive lithiation of diphenyl thioacetals or thioketals with lithium 1-(dimethylamino)naphthalenide, treatment of the resulting anion with trimethylsilyl chloride,
- Cohen, Theodore,Sherbine, James P.,Matz, James R.,Hutchins, Robert R.,McHenry, Barry M.,Willey, Paul R.
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p. 3245 - 3252
(2007/10/02)
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- Reactions of the Cyclopropanone Hemiketal Magnesium Salt with Some Nucleophilic Reagents
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Cyclopropanol (5), 1-(arylethynyl)cyclopropanol (7), 1-(3-hydroxypropyl)cyclopropanol derivative 10, 1-(2-propynyl)cyclopropanol (14), cyclopropanone cyanohydrin (19), 1-(aminomethyl)cyclopropanol (21) derivatives, benzylidenecyclopropanes 32, and ethyl cyclopropylideneacetate (38) have been prepared from the magnesium salt of cyclopropanone hemiketal 3. 3-Cyclopropylidene-1-propanol (12) and 3-cyclopropylidene-1-propyne (16) have been obtained from the cyclopropanols 10 and 14, respectively. Some reactions of this new synthon were specific. On the other hand, 3 did not undergo the nucleophilic addition of sulfur and nitrogen ylides; it underwent oxidizing ring opening with BrZnCH2COOEt and induced the decomposition of diazomethane.
- Salauen, Jacques,Bennani, Fatima,Compain, Jean-Claude,Fadel, Antoine,Ollivier, Jean
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p. 4129 - 4135
(2007/10/02)
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