- Photo-Organocatalysis of Atom-Transfer Radical Additions to Alkenes
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We have found that an organic molecule as simple as p-anisaldehyde efficiently catalyzes the intermolecular atom-transfer radical addition (ATRA) of a variety of haloalkanes onto olefins, one of the fundamental carbon-carbon bond-forming transformations i
- Arceo, Elena,Montroni, Elisa,Melchiorre, Paolo
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- SYNTHESIS OF ESTERS OF 2-SUBSTITUTED 4-KETOPENTANOIC ACIDS BY THE ALKYLATION OF CH-ACIDS USING CHLOROACETONE UNDER PHASE TRANSFER CATALYSIS CONDITIONS
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An improved method was developed for the synthesis of ethyl esters of 2-substituted 4-ketopentanoic acids by the alkylation of CH2(X)CO2Et using chloroacetone in the liquid-solid KOH (K2CO3 or Na2CO3)-DMF-PhCH2(Et)3NCl system.
- Sizov, A. Yu.,Yanovskaya, L. A.,Dombrovskii, V. A.
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- Gold N-Heterocyclic Carbene Catalysts for the Hydrofluorination of Alkynes Using Hydrofluoric Acid: Reaction Scope, Mechanistic Studies and the Tracking of Elusive Intermediates
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An efficient and chemoselective methodology deploying gold-N-heterocyclic carbene (NHC) complexes as catalysts in the hydrofluorination of terminal alkynes using aqueous HF has been developed. Mechanistic studies shed light on an in situ generated catalyst, formed by the reaction of Br?nsted basic gold pre-catalysts with HF in water, which exhibits the highest reactivity and chemoselectivity. The catalytic system has a wide alkyl substituted-substrate scope, and stoichiometric as well as catalytic reactions with tailor-designed gold pre-catalysts enable the identification of various gold species involved along the catalytic cycle. Computational studies aid in understanding the chemoselectivity observed through examination of key mechanistic steps for phosphine- and NHC-coordinated gold species bearing the triflate counterion and the elusive key complex bearing a bifluoride counterion.
- Bédard, Sandrine,Cavallo, Luigi,Falivene, Laura,Gauthier, Rapha?l,Nolan, Steven P.,Paquin, Jean-Fran?ois,Saab, Marina,Tzouras, Nikolaos V.,Van Hecke, Kristof,Zhang, Ziyun
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supporting information
(2021/12/09)
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- Copper-Catalyzed Cross-Nucleophile Coupling of β-Allenyl Silanes with Tertiary C-H Bonds: A Radical Approach to Branched 1,3-Dienes
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Described herein is a distinctive approach to branched 1,3-dienes through oxidative coupling of two nucleophilic substrates, β-allenyl silanes, and hydrocarbons appending latent functionality by copper catalysis. Notably, C(sp3)-H dienylation proceeded in a regiospecific manner, even in the presence of competitive C-H bonds that are capable of occurring hydrogen atom transfer process, such as those located at benzylic and other tertiary sites, or adjacent to an oxygen atom. Control experiments support the intermediacy of functionalized alkyl radicals.
- Shan, Qi-Chao,Hu, Lu-Min,Qin, Wei,Hu, Xu-Hong
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supporting information
p. 6041 - 6045
(2021/08/03)
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- Cu(OAc)2-Triggered Cascade Reaction of Malonate-Tethered Acyl Oximes with Indoles, Indole-2-alcohols, and Indole-2-carboxamides
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A Cu(OAc)2-promoted cascade reaction of malonate-tetherd acyl oximes with indoles, indole-2-alcohols, or indole-2-carboxmides provides facile access to polysubstituted 3-pyrrolin-2-ones. The reaction features the generation of two adjacent elec
- Mao, Peng-Fei,Zhou, Li-Jin,Zheng, An-Qi,Miao, Chun-Bao,Yang, Hai-Tao
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supporting information
p. 3153 - 3157
(2019/05/10)
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- METHOD OF CONTROLLING PLANTS
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The present invention provides a method of controlling plants comprising applying to the plants, or to the locus of the plants a composition comprising (A) a compound of formula (I) selected from the group consisting of: Formula(I), or an N-oxide or salt form thereof, and (B) one or more further herbicides.
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Page/Page column 29
(2018/02/28)
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- HERBICIDAL PYRIDAZINONE COMPOUNDS
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The present invention relates to compounds of Formula (I), or an agronomically acceptable salt of said compounds wherein R1a, R1b, R2, X, A, Ra, Rb, Rc, Rd and m are as defined herein. The invention further relates to herbicidal compositions which comprise a compound of Formula (I), to their use for controlling weeds. The invention further relates to intermediate compounds used to produce compounds of Formula (I).
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Page/Page column 25
(2018/05/24)
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- HERBICIDAL PYRIDAZINONE COMPOUNDS
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The present invention relates to compounds of Formula (I), or an agronomically acceptable salt of said compounds wherein A1, R1, Ra, Rb, Rc and Rd are as defined herein. The invention further relates to herbicidal compositions which comprise a compound of Formula (I), to intermediate compounds used to produce compounds of Formula (I), to processes for producing compounds of Formula (I) and to the use of compounds of Formula (I) for controlling weeds, in particular in crops of useful plants.
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Page/Page column 57
(2017/11/10)
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- Tin-free radical alkylation of ketones via N-silyloxy enamines
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The radical alkylation of ketones is achieved by their conversion into corresponding N-silyloxy enamines, followed by a radical reaction with alkyl halides bearing electron-withdrawing groups. The Royal Society of Chemistry 2006.
- Song, Hyun-Ji,Lim, Che Jo,Lee, Sunggi,Kim, Sunggak
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p. 2893 - 2895
(2008/09/18)
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- Reactions of per-O-acetylglucosyl isothiocyanate with carbon bases. A new method for the stereocontrolled syntheses of nucleosides and glucosylaminothiophenes
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Reaction of 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate 5 with diethyl malonate in a basic medium gave the corresponding glucopyranosyl thioamide without significant deacetylation. This thioamide in solution presents Z-anti as the sole configuration. Reactions of 5 with carbanions which have an ethoxycarbonyl group are a way to prepare anomerically pure N- nucleoside derivatives of pyrrole and tetrahydropyridine. Reactions of 5 with carbanions stabilized by one cyano group are used to prepare glucosylamino thiophenes with only the β-configuration. Some other stereochemical aspects of the prepared compounds are discussed.
- Fuentes, Jose,Molina, Jose L.,Pradera, M. Angeles
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p. 2517 - 2532
(2007/10/03)
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- Cyclohexenone derivatives
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Cyclohexenone derivatives I STR1 The cyclohexenone derivatives I are suitable as herbicides and for regulating plant growth.
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- Furanyl insecticide
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The present invention relates to novel (tetrahydro-3-furanyl)methylamino derivatives of the following formula (1): STR1 wherein the variables are defined in the specification, which are useful as insecticides.
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- Preparation and Reactivities of (η3-1- and 2-Trimethylsiloxyallyl)Fe(CO2)NO Complexes. Intermediates Functioning as Equivalents of β- and α-Acyl Carbocations and Acyl Carbanions
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(η3-1- and 2-Trimethylsiloxyallyl)Fe(CO)2NO complexes were prepared by the reaction of the corresponding siloxyallylic halides with Bu4N.These complexes reacted with both of carbon nucleophiles and carbon electrophiles preferentially at the less hindered sites of the allylic ligands.In these reactions, (η3-1-trimethylsiloxyallyl)Fe(CO)2NO complexes served as synthetically equivalent synthons for both of β-acyl carbocations and β-acyl carbanions and (η3-2-trimethylsiloxyallyl)Fe(CO)2NO complexes as both of α-acyl carbocations and α-acyl carbanions.The stereochemical courses of the reactions are described.
- Itoh, Keiji,Nakanishi, Saburo,Otsuji, Yoshio
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p. 2965 - 2977
(2007/10/02)
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- 3-Chloro-2-(trimethylsiloxy)-1-propene as an Electrophilic Acetonyl Equivalent. A Novel Regioselective Synthesis of 1,4-Dicarbonyl Compounds
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α-Metalated imines, hydrazones, and activated methylene compounds are acetonylated with 3-chloro-2-(trimethylsiloxy)-1-propene in high yield.Highly regioselective acetonylation at either the tertiary or secondary α-carbon of 2-methylcyclohexanone can be carried out by selecting the reaction conditions.
- Hosomi, Akira,Shirahata, Akihiko,Araki, Yoshitaka,Sakurai, Hideki
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p. 4631 - 4633
(2007/10/02)
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- Malonate Anion Induced Favorskii Type Rearrangement. 21. Reaction of Acyclic α-Halo Ketones with Carbanions Leading to Cyclopropanols2
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The reaction of 3-bromo-3-methyl-2-butanone (6a) with ethyl sodiomalonate (2) in refluxing THF gave 1--2,2-dimethylcyclopropanol (9a), the Favorskii-type intermediate, in 51percent yield.Similar reactions of acyclic halo ketones such as 2-bromo-2-methyl-3-pentanone (6b), 1-acetyl-1-bromocyclohexane (6c), and 1-acetyl-1-bromocyclopentane (6d) with 2 also gave the corresponding cyclopropanols 9b-d in 42-56percent yields.On the contrary, the α-halo ketones (6f-l) possessing a primary or secondary carbon atom at the α position afforded the SN2 products10f-l.The behavior of 3-chloro-3-methyl-2-butanone (6e) was quite different from that of its bromo homologue 6a, giving a mixture (16:45:39) of 9a, 1,1-bis-2,2-dimethylcyclopropane (14), and 1--2,2-dimethyl-1-cyclopropane (15) in 75percent total yield.Hydrolysis of 9a with 0.2 N NaOH at room temperature gave the acid ester 18, which afforded a mixture of 3-carboxy-4,5,5-trimethyl-2(5H)-furanone (22a, 27percent yield) and its ethyl ester (22b, 39percent yield) on heating.When the hydrolysis was carried out in 2 N NaOH at 10 deg C, 9a gave 1-(dicarboxymethyl)-2,2-dimethylcyclopropanol (23, 60percent yield) together with 22a (27percent yield).Similar hydrolysis of 9a at 30 deg C afforded 4,4-dimethyl-3-oxopentanoic acid (24, 38percent yield) and 3,3-dimethyl-2-butanone (25, 18percent yield).The bromination of 9a with Br2 caused the ring opening to give ethyl 5-bromo-4,4-dimethyl-2-(ethoxycarbonyl)-3-oxopentanoate (30) in 76percent yield.The ester 30 was cyclized to the oxetane 31 in 77percent yield.
- Sakai, Takashi,Katayama, Tsuyoshi,Takeda, Akira
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p. 2924 - 2931
(2007/10/02)
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