- Selective Activation of Unstrained C(O)-C Bond in Ketone Suzuki-Miyaura Coupling Reaction Enabled by Hydride-Transfer Strategy
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A Rh(I)-catalyzed ketone Suzuki-Miyaura coupling reaction of benzylacetone with arylboronic acid is developed. Selective C(O)-C bond activation, which employs aminopyridine as a temporary directing group and ethyl vinyl ketone as a hydride acceptor, occurs on the alkyl chain containing a β-position hydrogen. A series of acetophenone products were obtained in yields up to 75%.
- Zhong, Jing,Zhou, Wuxin,Yan, Xufei,Xia, Ying,Xiang, Haifeng,Zhou, Xiangge
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supporting information
p. 1372 - 1377
(2022/02/23)
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- Dealkenylative Ni-Catalyzed Cross-Coupling Enabled by Tetrazine and Photoexcitation
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A new and general method to functionalize the C(sp3)-C(sp2) bond of alkyl and alkene linkages has been developed, leading to the dealkenylative generation of carbon-centered radicals that can be intercepted to undergo Ni-catalyzed C(sp3)-C(sp2) cross-coupling. This one-pot protocol leverages the easily procured alkene feedstocks for organic synthesis with excellent functional group compatibility without the need for a photoredox catalyst.
- Cao, Yuhui,Che, Jinteng,Chen, Han,Chen, Si-Cong,Fang, Xianhe,Guo, Yinliang,Guo, Zhixian,Kong, Lingran,Li, Chen,Lu, Jia-Tian,Luo, Tuoping,Zhang, Nan,Zhu, Qi
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supporting information
p. 14046 - 14052
(2021/09/13)
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- Terminal-Selective C(sp3)-H Arylation: NiH-Catalyzed Remote Hydroarylation of Unactivated Internal Olefins
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A terminal-selective migratory hydroarylation of unactivated olefins has been developed though a NiH-catalyzed alkene isomerization-hydroarylation relay process. This sp3C-H arylation was achieved with a simple pyrox ligand under mild conditions. The practicality and synthetic flexibility of the method is highlighted by the successful regioconvergent conversion of isomeric mixtures of alkenes to value-added linear arylation products on a gram scale.
- He, Yuli,Han, Bo,Zhu, Shaolin
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supporting information
p. 2253 - 2264
(2021/05/05)
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- Nickel-Catalyzed Reductive Cross-Coupling of Aryl Halides with Monofluoroalkyl Halides for Late-Stage Monofluoroalkylation
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A combinatorial nickel-catalyzed monofluoroalkylation of aryl halides with unactivated fluoroalkyl halides by reductive cross-coupling has been developed. This method demonstrated high efficiency, mild conditions, and excellent functional-group tolerance, thus enabling the late-stage monofluoroalkylation of diverse drugs. The key to success was the combination of diverse readily available bidentate and monodentate pyridine-type nitrogen ligands with nickel, which in situ generated a variety of readily tunable catalysts to promote fluoroalkylation with broad scope with respect to both coupling partners. This combinatorial catalysis strategy offers a solution for nickel-catalyzed reductive cross-coupling reactions and provides an efficient way to synthesize fluoroalkylated druglike molecules for drug discovery.
- Sheng, Jie,Ni, Hui-Qi,Zhang, Hao-Ran,Zhang, Kai-Fan,Wang, Yi-Ning,Wang, Xi-Sheng
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supporting information
p. 7634 - 7639
(2018/06/26)
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- INTERMEDIATES AND PROCESS FOR THE PREPARATION OF HIGH PURITY FINGOLIMOD HYDROCHLORIDE
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The present invention relates to a simple and commercially feasible preparation of Fingolimod hydrochloride with high purity of greater than 99.9%. The.present invention also provides novel intermediates for the preparation of Fingolimod Hydrochloride of Formula 1.
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- Synthesis, insecticidal evaluation of novel 1,3,4-thiadiazole chrysanthemamide derivatives formed by an EDCI/HOBt condensation
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A series of novel pesticides with two components derived from a 1,3,4-thiadiazole and chrysanthemic acid were synthesised via an EDCI/HOBt condensation. These 1,3,4-thiadiazole chrysanthemamides were identified by IR, 1H NMR and elemental analyses. Their insecticidal activity was also evaluated.
- Yu, Peng,Hu, Jun,Zhou, Tao-Yu,Wang, Peng,Xu, Yan-Hua
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p. 703 - 706
(2012/03/10)
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- Nickel-catalyzed reductive cross-coupling of aryl halides with alkyl halides
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(Chemical Equation Presented) The direct reductive cross-coupling of alkyl halides with aryl halides is described. The transformation is efficient (equimolar amounts of the starting materials are used), generally high-yielding (all but one between 55 and 88% yield), highly functional-group-tolerant [OH, NHBoc, NHCbz, Bpin, C(O)Me, CO2Et, and CN are all tolerated], and easy to perform (uses only benchtop-stable reagents, tolerates small amounts of water and oxygen, changes color when complete, and uses filtration workup). The reaction appears to avoid the formation of intermediate organomanganese species, and a synergistic effect was found when a mixture of two ligands was employed.
- Everson, Daniel A.,Shrestha, Ruja,Weix, Daniel J.
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supporting information; experimental part
p. 920 - 921
(2010/03/31)
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- Method for producing Suzuki coupling compound catalysed by a nickel compound
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There are disclosed a method for producing a cross-coupling compound of formula (3):(Y-)(n-1)R1-R2-(R1)(n'-L) ???wherein R1 represents ???a substituted or unsubstituted, linear, branched, or cyclic hydrocarbon group, and ???n and n' each represent 1 or 2, ???provided that when n and n' are the same, both n and n' are not 2, ???R2 represents a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl or substituted or unsubstituted alkenyl group, ???and ???Y represents R2 or X1, wherein R2 is as defined above, and X1 represents a chlorine, bromine or iodine atom, ???which method comprises reacting ???an organic halide of formula (1):n'(R1X1?n), ???wherein R1 is as defined above and carbon atoms at the α and β positions relative to X1 are sp3 carbon atoms, and X1, n and n' are as defined above, ???with a boron compound of formula (2):m{R2(BX2?2)n'}, ???wherein R2 and n' are as defined above, ???X2 independently represents a hydroxyl group or an alkoxy or aryloxy group, or X22 together form an alkoxy or aryloxy group, and m represents 1 or 2, and m≤n, and the boron atom is bonded with an sp2 carbon atom of R2 group, or a boronic acid trimer anhydride thereof, in the presence of a base and a catalyst comprising a nickel compound and a compound of formula (i): ???wherein R3 represents a substituted or unsubstituted alkyl group, ???R4 represents a hydrogen atom or a substituted or unsubstituted alkyl group, ???1 represents an integer of 1 to 3, and ???p and q each represents an integer of 0 to 2; and a catalyst.
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- Tetraphosphine/palladium catalysed Suzuki cross-coupling reactions of aryl halides with alkylboronic acids
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Through the use of [PdCl(C3H5)]2/cis,cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane as a catalyst, a range of aryl bromides and chlorides undergoes Suzuki cross-coupling with alkylboronic acids in good yields. Several alkyl substituents such as ethyl, n-butyl, n-octyl, isobutyl or 2,2-dimethylpropyl on the alkylboronic acids have been successfully used. The functional group tolerance on the aryl halide is remarkable; substituents such as fluoro, methyl, methoxy, acetyl, formyl, benzoyl, nitro or nitrile are tolerated. Furthermore, this catalyst can be used at low loading, even for reactions of sterically hindered aryl bromides.
- Kondolff, Isabelle,Doucet, Henri,Santelli, Maurice
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p. 3813 - 3818
(2007/10/03)
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- Syndiospecific synthesis of longer p-n-alkyl-substituted polystyrenes using monocyclopentadienyl-type titanium catalysts
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Substituted styrenes with linear alkyl substituents (C6 to C12) at the para position on the ring were synthesized and polymerized using the (Me)5CpTi(OMe)3/MAO catalytic system. Increased polymerization activiti
- Quirk, Roderic P.,Ok, Myung-Ahn
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p. 3976 - 3982
(2007/10/03)
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- Highly active catalyst for the heterogeneous Suzuki-Miyaura reaction: Assembled complex of palladium and non-cross-linked amphiphilic polymer
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An assembled insoluble catalyst, PdAS, prepared from palladium ((NH 4)2PdCl4 (1)) and non-cross-linked amphiphilic copolymer poly(N-isopropylacrylamide-co-4-diphenylstyrylphosphine) (2) was developed. It was found that PdAS is an excellent catalyst for the Suzuki-Miyaura reaction on three points: (1) The use of 8 × 10 -7 to 5 × 10-4 mol equiv of PdAS afforded the coupling products efficiently after easy workup, with the turnover number reaching up to 1 250 000. (2) The catalyst was reusable many times without loss of catalytic activity. (3) PdAS showed good stability in any reaction medium (i.e., water or aqueous or anhydrous organic solvents). Analytical study of PdAS indicates that the phosphines in 2 coordinate to palladium to form PdCl2(PPh2Ar)2 species.
- Yamada, Yoichi M. A.,Takeda, Koji,Takahashi, Hideyo,Ikegami, Shiro
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p. 7733 - 7741
(2007/10/03)
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- Production of 2-amino-2-[2-(4-C2-20-alkyl-phenyl)ethyl]propane-1,3-diols
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Disclosed is a process for the production of 2-amino-2-[2-(4-C2-20-alkyl-phenyl)ethyl]propane-1,3-diols.
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- Polystyrene anion exchange polymer pharmaceutical composition
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Polystyrene polymers having a quaternised ammonium group and their use in a method of treatment of hypercholesterolaemia. A particular compound of the invention is (N,N-dimethyl-N-dodecyl-ammoniomethylstyrene-ethyl methacrylate-divinylbenzene co-polymer,
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- Polymer compounds
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Polymers of structure (I) in which X is a co-monomer unit; X1 is a cross-linking unit; R1 is a saturated or unsaturated C6 to C20 alkyl group; R2 and R3 are the same or different and are each C1 4alky
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- A wide range of organosilicon compounds couples with enol and aryl triflates in the presence of Pd catalyst and fluoride ion
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Under the influence of tetrakis(triphenylphosphine)palladium and tetrabutylammonium fluoride, the title reaction took place with alkenyl, alkynyl, aryl, and alkylsilanes to give the corresponding coupled products in good yields with high chemoselectivity and stereospecificity.
- Hatanaka, Yasuo,Hiyama, Tamejiro
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p. 2719 - 2722
(2007/10/02)
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- The Synthesis of 3-Aryl-6-alkylpyridazines
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Nine compounds of general structure R-X-Y-R' where X is a para-disubstituted phenyl ring and Y is a 3,6-disubstituted-pyridazine ring were synthesized.These can be used as liquid crystal dopents.A general procedure for their synthesis was developed.N-Alkyl benzene and ethyl butyrylacetate were used as starting materials.The purification of reaction intermediates was not necessary if preparative hplc was used to purify the final products.Very pure materials were obtained with good yield.Their structure was confirmed by carbon 13 nmr.
- Liang, Jason
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p. 1297 - 1299
(2007/10/02)
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- Multiple Melting Behaviour in Square-planar trans-Bis-(1-p-n-alkylphenylbutane-1,3-dionato)copper(II) - The Effect of Alkyl Chain Length
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The title complexes having different n-alkyl groups from methyl to dodecyl have synthesized.All these complexes exhibit solid polymorphism.The number of polymorphs depends on the length of the alkyl chain: two for n (the number of carbon atoms) = 0-2, three for n = 3-5 and 12, and four for n = 6-11, respectively.Each polymorphic form except those with the highest m.p.s. exhibits multiple melting behaviour: double melting for n = 0-5,8, and 12, and triple melting for n = 6-11 except 8.The m.p.s. of the complexes with alkyl groups of odd carbon atoms are higher than those with even atoms, while the respective ligand solids show the opposit e even-odd effect in their m.p.s.
- Ohta, Kazuchika,Jiang, Guang-Jie,Yokoyama, Masaaki,Kusabayashi, Shigekazu,Mikawa, Hiroshi
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p. 283 - 294
(2007/10/02)
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- Study of the Influence of Molecular Length on the Characteristics of the Ordered Smectic Phase.
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Study of DTA and X-rays of p-phenyl-benzylidene-p'-alkylanilines of mesomorphic phases demonstrates the predominant role of the aliphatic chain length. In effect, it governs the appearance of the different phases; the correlation between layers decreases for greater chain lengths. The nonlinear variations of SmB layer thickness for these compounds shows clearly the importance of steric effects coupled with the molecular length with respect to the dipolar effect.
- Benattar,Levelut,Strzelecki
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p. 1233 - 1240
(2007/10/05)
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- MESOMORPHIC TRANSITION METAL COMPLEXES.
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The synthesis of two dithiolato nickel complexes carrying aliphatic substituents is described. Both compounds exhibit mesomorphic properties.
- Giroud,Mueller-Westerhoff
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