- Anion ligand promoted selective C-F bond reductive elimination enables C(sp2)-H fluorination
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A detailed mechanism study on the anion ligand promoted selective C-H bond fluorination is reported. The role of the anion ligand has been clarified by experimental evidence and DFT calculations. Moreover, the nitrate promoted C-F bond reductive elimination enabled a selective C-H bond fluorination of various symmetric and asymmetric azobenzenes to access diverse o-fluoroanilines.
- Mao, Yang-Jie,Luo, Gen,Hao, Hong-Yan,Xu, Zhen-Yuan,Lou, Shao-Jie,Xu, Dan-Qian
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supporting information
p. 14458 - 14461
(2019/12/09)
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- Iron(III)-Catalyzed Chlorination of Activated Arenes
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A general and regioselective method for the chlorination of activated arenes has been developed. The transformation uses iron(III) triflimide as a powerful Lewis acid for the activation of N-chlorosuccinimide and the subsequent chlorination of a wide range of anisole, aniline, acetanilide, and phenol derivatives. The reaction was utilized for the late-stage mono- and dichlorination of a range of target compounds such as the natural product nitrofungin, the antibacterial agent chloroxylenol, and the herbicide chloroxynil. The facile nature of this transformation was demonstrated with the development of one-pot, tandem, iron-catalyzed dihalogenation processes allowing highly regioselective formation of different carbon-halogen bonds. The synthetic utility of the resulting dihalogenated aryl compounds as building blocks was established with the synthesis of natural products and pharmaceutically relevant targets.
- Mostafa, Mohamed A. B.,Bowley, Rosalind M.,Racys, Daugirdas T.,Henry, Martyn C.,Sutherland, Andrew
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p. 7529 - 7537
(2017/07/26)
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- Under the conditions of a solvent-free method of hydrogenation to synthesize haloarylamine
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The invention provides a method for synthesising halogenated aromatic amine through hydrogenation in a solvent-free condition. The method comprises the following step of: carrying out a liquid-phase hydrogenation reaction on the halogenated aromatic nitro compound shown in formula (I) under the action of hydrogen, in the absence of a solvent and a dehalogenation inhibitor under the action of a carbon-supported large-particle-size precious metal catalyst to prepare the halogenated aromatic amine shown in formula (II). The method provided by the invention is capable of achieving the effect of inhibiting a hydrogenation dehalogenation side reaction in the case of not adding a dehalogenation inhibitor, is high in target product selectivity, and is capable of remarkably increasing the reaction speed.
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Paragraph 0050-0053
(2017/03/21)
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- Regioselective chlorination and bromination of unprotected anilines under mild conditions using copper halides in ionic liquids
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By using ionic liquids as solvents, the chlorination or bromination of unprotected anilines at the para-position can be achieved in high yields with copper halides under mild conditions, without the need for potentially hazardous operations such as supplementing oxygen or gaseous HCl.
- Wang, Han,Wen, Kun,Nurahmat, Nurbiya,Shao, Yan,Zhang, He,Wei, Chao,Li, Ya,Shen, Yongjia,Sun, Zhihua
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supporting information; experimental part
p. 744 - 748
(2012/06/30)
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- Facile synthesis and herbicidal activities of new isoxazole derivatives via 1,3-dipolar cycloaddition reaction
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A series of cycloadducts via 1,3-dipolar cycloaddition reactions of generated nitrile oxides with N-(4-chloro-2-fluorophenyl) maleimides were described. The reaction of N-(4-chloro-2-fluorophenyl) maleimides with nitrile oxides gave 3,5-diaryl-3a,6a-dihydropyrroio[3,4-d]isoxazole-4,6-diones through syn-addition pattern. The title compounds were characterized by 1H NMR, IR, MS, and elemental analysis or HRMS. The single crystal structure of 6i was determined by X-ray diffraction. The herbicidal activities of the title compounds were evaluated. Some of them exhibited certain herbicidal activities against barnyardgrass and rape.
- Zhang, Chuan-Yu,Wang, Bao-Lei,Liu, Xing-Hai,Li, Yong-Hong,Wang, Su-Hua,Li, Zheng-Ming
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experimental part
p. 397 - 404
(2010/03/24)
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- Electrophilic aromatic fluorination with fluorine: meta-Directed fluorination of anilines
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Anilines are mainly or selectively fluorinated in the meta-position with F2 when dissolved in triflic acid, sometimes in the presence of small quantities of antimony pentafluoride. The regioselectivity is increased when an electron-donating substituent is present at the para-position.
- Alric,Marquet,Billard,Langlois
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p. 661 - 667
(2007/10/03)
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- SUBSTITUTED QUINAZOLINE DERIVATIVES AND THEIR USE AS INHIBITORS
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The use of a compound of formula (I) 1 or a salt, ester or amide thereof; where X is O, or S, S(O) or S(O)2, or NR6 where R6 is hydrogen or C1-6 alkyl,; R5 is an optionally substituted 5-membered heteroaromatic ring, R1, R2 ,R3, R4 are independently selected from various specified moieties, in the preparation of a medicament for use in the inhibition of aurora 2 kinase. Certain compounds are novel and these, together with pharmaceutical compositions containing them are also described and claimed
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- Herbicidal aryl triazolinones
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Herbicidal compounds of the formula STR1 in which, for example, X is Br, Cl or F; Y is Cl or Br, R2 is CHF2, R3 is CH3, R is alkyl, dialkylamino, carboxymethyl, hydroxy, haloalkyl, or aryl, and R1 is H, Na, lower alkyl or --SO2 R.
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- Herbicidal aryl triazolinones
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Herbicidal compounds of the formula STR1 in which, for example, X is Br, Cl or F; Y is Cl or Br, R2 is CHF2, R3 is CH3 R is lower alkyl and R1 is H,Na, lower alkyl or --SO2 R.
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- Substituted amino acids
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Esters and thiolesters of amino acids, intermediates therefor, synthesis thereof, and the use of said esters and thiolesters and compositions for the control of pests.
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- Cycloalkanapyrazole-3-carbonitrile herbicides
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Herbicidal cycloalkanapyrazoles of the formula: STR1 where N IS 3, 4 OR 5; R1 is hydrogen or methyl; X is fluorine, chlorine, bromine, iodine, cyano, or methoxy; Y is hydrogen, fluorine, or chlorine; Z is hydrogen or fluorine; and V is hydrogen, fluorine, chlorine or methoxy; provided that (a) when n is 3, R1 must be hydrogen; (b) when n is 5, R1 must be hydrogen, Y must be hydrogen or fluorine, Z and V must both be hydrogen, and X must be fluorine, chlorine or bromine; (c) when V is methoxy, X and Y must be chlorine, and Z must be hydrogen; and (d) when V is fluorine or chlorine, X must be fluorine, chlorine or bromine, and Z must be hydrogen.
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- Alkyl-substituted cycloalkanapyrazole herbicides
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Herbicidal alkyl-substituted cycloalkanapyrazoles of the formula: STR1 where N IS 3, 4 OR 5; R1 is hydrogen or methyl; Q is methyl; X is fluorine, chlorine, bromine, iodine, cyano or methoxy; Y is hydrogen, fluorine or chlorine; Z is hydrogen or fluorine; V is hydrogen, fluorine, chlorine or OR; and R is alkyl of 1 to 4 carbon atoms; with the proviso that A. when n is 3, R1 is hydrogen; B. when n is 5, R1 is hydrogen, Y is hydrogen or fluorine, Z and V are hydrogen and X is fluorine, chlorine or bromine; C. when V is OR, X and Y are chlorine and Z is hydrogen; D. when V is fluorine or chlorine, X is fluorine, chlorine or bromine and Z is hydrogen. Preferred for their higher activity or favorable cost or both are those compounds of formula I where, independently, 1. R1 is hydrogen and n is 4, 2. Y is hydrogen or fluorine, V is hydrogen and Z is hydrogen. Most preferred for their outstanding herbicidal activity are those compounds of formula I where n is 4, R1 is hydrogen, X is fluorine, chlorine or bromine, Y is hydrogen or fluorine, V is hydrogen and Z is hydrogen.
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- Cycloalkanapyrazole herbicides
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Herbicidal cycloalkanapyrazoles of the formula: STR1 where N IS 3, 4 OR 5; R1 is hydrogen or methyl; Q is fluorine, chlorine, bromine or iodine; X is fluorine, chlorine, bromine, iodine, cyano, methoxy or nitro; Y is hydrogen, fluorine, or chlorine; Z is hydrogen or fluorine; and V is hydrogen, fluorine, chlorine or methoxy with the proviso that A. when n is 5, R1 must be hydrogen, Q must be chlorine or bromine, Z and V must both be hydrogen and Y must be hydrogen or fluorine; B. when n is 3 or 4 and Q is fluorine or iodine, R1, Z and V must be hydrogen and Y must be hydrogen or fluorine; C. when n is 3 and R1 is methyl, Q must be chlorine or bromine, Y must be hydrogen or fluorine and Z and V must both be hydrogen; and, D. when V is other than hydrogen, X must be fluorine, chlorine or bromine and Z must be hydrogen.
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- 2-(Substituted-phenyl)-hexahydro- and tetrahydro-3-(2H)-cinnolinones as herbicides
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This invention relates to herbicidal 2-(substituted-phenyl)-hexahydro- and tetrahydro-3-(2H)-cinnolinones, to agricultural compositions containing such compounds, and to the method of use of these compounds as pre- and post-emergence herbicides.
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- 2-Aryl-3-chloro-2,4,6,7-tetrahydrothiopyrano[4,3-c]-pyrazoles
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Compounds of the formula STR1 where N IS 0, 1, OR 2; Q is chlorine or bromine; X is fluorine, chlorine, bromine, or cyano; Y is hydrogen, fluorine, or chlorine; and V is hydrogen, fluorine, chlorine or alkoxy of 1 to 3 carbon atoms.
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- Herbicidal 2-arylaminocarbonyl-1-cyclohexene-1-carboxylic acids and salts thereof
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This invention relates to herbicidal 2-arylaminocarbonyl-1-cyclohexene-1-carboxylic acids and salts thereof. These compounds may be used for selective weed control in certain crops or for total vegetation control.
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- 2-Aryl-5,6,7,8-tetrahydroimidazo[1,5a]-pyridine-1,3(2H,8aH)-diones as herbicides
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This invention relates to novel 2-Aryl-5,6,7,8-tetrahydroimidazo[1,5a]-pyridine-1,3(2H,8aH)-diones and their use as herbicides. These novel compounds may be used for selective weed control in certain crops or for total vegetation control.
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- Herbicidal isoindol-1-one derivatives
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This invention relates to herbicidal isoindol-1-one derivatives. These compounds have the general formulae: SPC1 Wherein R1 is hydrogen or methyl; R2 is hydrogen or alkyl of 1 to 4 carbons; X is fluorine, chlorine or bromine; Y is hydrogen or fluorine; Z is hydrogen or fluorine, provided that when Y and Z are both fluorine, X must also be fluorine; and A is --(CH2)4 -- or --CH=CH--CH=CH--, provided that when A is --CH=CH--CH=CH-- and Y is hydrogen, Z must be fluorine. Both geometric isomers, Formulae IIa and IIb, are encompassed by this invention. In particular, these compounds have demonstrated that they are active pre- and post-emergence herbicides and tend to do minimal damage to certain desirable crops, e.g., corn and wheat.
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- Herbicidal isobenzofuranones
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This invention relates to herbicidal isobenzofuranones. These compounds may be used for selective weed control in certain crops or for total vegetation control.
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- Herbicidal 2-(substituted aryl)-3a,4,5,6,7,7a-hexahydro-1H-isoindole-1,3(2H)-diones
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This invention relates to herbicidal 2-(substituted aryl)-3a,4,5,6,7,7a-hexahydro-1H-isoindole-1,3(2H)-diones. These compounds may be used for selective weed control for certain crops or for total vegetation control. In particular, the compounds may be utilized as rice herbicides and have the formula SPC1 Wherein X is Cl, Br or F, and Y is H or F, provided that when Y is F, X is F.
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