- Copper-catalyzed intramolecular C(sp3)-H and C(sp2)-H amidation by oxidative cyclization
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The first copper-catalyzed intramolecular C(sp3)-H and C(sp 2)-H oxidative amidation has been developed. Using a Cu(OAc) 2 catalyst and an Ag2CO3 oxidant in dichloroethane solvent, C(sp3)-H
- Wang, Zhen,Ni, Jizhi,Kuninobu, Yoichiro,Kanai, Motomu
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supporting information
p. 3496 - 3499
(2014/04/03)
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- Sulfoximine assisted Pd(II)-catalyzed bromination and chlorination of primary β-C(sp3)-H bond
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S-Methyl-S-2-pyridyl-sulfoximine (MPyS) directed bromination and chlorination of the 1°-β-C(sp3)-H bond of MPyS-N-amides is realized under the influence of N-Br/Cl-phthalimides and a Pd(II)-catalyst. The sequential halogenation and acetoxylation of α-dimethyl MPyS-N-amides constructs highly functionalized α-trisubstituted aliphatic acid derivatives. The MPyS directing group is cleaved from the halogenated products and recovered. (Chemical Equation Presented).
- Rit, Raja K.,Yadav, M. Ramu,Ghosh, Koushik,Shankar, Majji,Sahoo, Akhila K.
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supporting information
p. 5258 - 5261
(2015/01/09)
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- β-Arylation of carboxamides via iron-catalyzed C(sp3)-H bond activation
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A 2,2-disubstituted propionamide bearing an 8-aminoquinolinyl group as the amide moiety can be arylated at the β-methyl position with an organozinc reagent in the presence of an organic oxidant, a catalytic amount of an iron salt, and a biphosphine ligand at 50 C. Various features of selectivity and reactivity suggest the formation of an organometallic intermediate via rate-determining C-H bond cleavage rather than a free-radical-type reaction pathway.
- Shang, Rui,Ilies, Laurean,Matsumoto, Arimasa,Nakamura, Eiichi
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supporting information
p. 6030 - 6032,3
(2013/05/22)
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- Highly regioselective carbonylation of unactivated C(sp3)-H bonds by ruthenium carbonyl
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The regioselective carbonylation of unactivated C(sp3)-H bonds of aliphatic amides was achieved using Ru3(CO)12 as a catalyst. The presence of a 2-pyridinylmethylamine moiety in the amide is crucial for a successful reaction. The reaction shows a preference for C-H bonds of methyl groups as opposed to methylene C-H bonds and tolerates a variety of functional groups. The stoichiometric reaction of an amide with Ru 3(CO)12 gave a dinuclear ruthenium complex in which the 2-pyridinylmethylamino moiety was coordinated to the ruthenium center in an N,N manner.
- Hasegawa, Nao,Charra, Valentine,Inoue, Satoshi,Fukumoto, Yoshiya,Chatani, Naoto
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supporting information; experimental part
p. 8070 - 8073
(2011/07/08)
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- Indium-catalyzed coupling reaction between silyl enolates and alkyl chlorides or alkyl ethers
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The coupling reactions of alkyl chlorides with silyl enolates catalyzed by InBr3, and the coupling reactions of alkyl ethers with silyl enolates catalyzed by the combined Lewis acid of InBr3/Me3SiBr are described. In both reaction systems, various types of silyl enolates were used to give corresponding α-alkylated esters, ketones, carboxylic acids, amides, thioesters, and aldehydes.
- Nishimoto, Yoshihiro,Saito, Takahiro,Yasuda, Makoto,Baba, Akio
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experimental part
p. 5462 - 5471
(2009/12/01)
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- Coupling reaction of alkyl chlorides with silyl enolates catalyzed by indium trihalide
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Indium(III) halide catalyzed not only the coupling of alkyl chlorides with silyl enolates derived from esters, ketones, and aldehydes to give a variety of α-alkylated carbonyl compounds but also one-pot, three-component reactions of aldehyde enolate, alkyl chloride, and allylsilane or alkynylsilane.
- Nishimoto, Yoshihiro,Yasuda, Makoto,Baba, Akio
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p. 4931 - 4934
(2008/03/27)
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- Radical Substitution on the Sulphur of Thioester Group
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Intermolecular reaction of an organo-radical with thioester gives the sulphide, which is formed by the sulphur centred substitution of acyl groups with a nucleophilic organo-radical, but no displacement of S-alkyl groups with the organo-radical takes place.
- Tada, Masaru,Uetake, Tomohiro,Matsumoto, Mitsuhiro
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p. 1408 - 1409
(2007/10/02)
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- Indaneacetic acid derivatives
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This invention provides new compounds of formula I, STR1 wherein R1 is lower alkyl, R2 is hydrogen or lower alkyl, R3 is hydrogen or lower alkyl, R4 is hydrogen or lower alkyl, R5 is hydrogen, chlorine or lower alkyl, and each of R6 and R7 is hydrogen, or, when R5 is hydrogen, R6 may also be chlorine or lower alkyl, and R7 chlorine or lower alkyl, Useful as anti-phlogistic and anti-arthritic agents.
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