- Direct carboxylation of allylic halides with carbon dioxide in the presence of indium
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A highly regioselective indium-mediated allylation of carbon dioxide starting from simple allylic halides (X = I, Br, Cl) has been developed. No transition metal catalyst is needed and an inert atmosphere is not necessary. The reaction tolerates a wide range of synthetically attractive functional groups with a very high branched regioselectivity. The Royal Society of Chemistry 2014.
- Miao, Bukeyan,Ma, Shengming
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supporting information
p. 3285 - 3287
(2014/03/21)
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- Copper-catalyzed difluoromethylation of β,γ-unsaturated carboxylic acids: An efficient allylic difluoromethylation
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Not one but two! A new strategy for the regiospecific construction of compounds with allylic CF2H groups has been developed. The decarboxylative (phenylsulfonyl)difluoromethylation of β,γ- unsaturated carboxylic acids is catalyzed by a Lewis acid (CuCl 2·2 H2O), and the resulting product easily undergoes desulfonylation. Copyright
- He, Zhengbiao,Hu, Mingyou,Luo, Tao,Li, Lingchun,Hu, Jinbo
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supporting information
p. 11545 - 11547
(2013/01/15)
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- Rh-catalyzed highly enantioselective synthesis of 3-arylbutanoic acids
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(Chemical Equation Presented) It's in the mix: The reaction conditions - catalyst, additive, and solvent - have been optimized for the asymmetric hydrogenation of 3-aryl-3-butenoic acids. The rigid, chiral bisphospholane ligand (SP,RC)-DuanPhos is crucial to achieving high enantioselectivity.
- Sun, Xianfeng,Zhou, Le,Wang, Chun-Jiang,Zhang, Xumu
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p. 2623 - 2626
(2008/02/13)
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- Palladium-catalyzed cross-coupling of 3-iodobut-3-enoic acid with organometallic reagents. Synthesis of 3-substituted but-3-enoic acids
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3-Substituted but-3-enoic acids were obtained in good yields under mild experimental conditions by palladium-catalyzed cross-coupling of 3-iodobut-3-enoic acid with organozinc or organotin compounds using PdCl2(MeCN)2 as catalyst and DMF as solvent.
- Abarbri,Parrain,Kitamura,Noyori,Duchene
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p. 7475 - 7478
(2007/10/03)
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- 3-Aryl-3-butenoic Acids and Their Esters: Practical Synthesis from Diketene by the Palladium-Catalyzed Grignard Coupling Reaction and Application as Monomers for the Radical Copolymerization with Styrene
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Treatment of arylmagnesium bromide with an equimolar amount of zinc chloride followed by the reaction with diketene in the presence of a catalytic amount of PdCl2(PPh3)2 provided an improved synthetic method for 3-aryl-3-butenoic acid in a large scale.App
- Itoh, Kenji,Harada, Tatsumi,Nagashima, Hideo
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p. 3746 - 3748
(2007/10/02)
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- Optimization of asymmetric hydrogenation of 3-phenyl-3-butenoic acid catalyzed by rhodium(I)-4,5-bis-2,2-dimethyldioxolane (DIOP)
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Enantioselective, homogeneous hydrogenation of 3-phenyl-3-butenoic acid (1) has extensively been examined in the presence of the rhodium(I)/4,5-bis-2,2-dimethyldioxolane (DIOP) catalyst systems.Optimization of the reaction conditions was undertaken mainly by controlling effects of added tertiary amines as well as solvent polarities on the enantio-selectivity of the product.The best asymmetric yield (85.1percent e.e.) was attained when the hydrogenation was carried out in the presence of triethylamine (5 molpercent) in 75percent aqueous methanol using a neutral rhodium-DIOP catalyst.
- Yamamoto, Keiji,Ikeda, Kiyoshi,Yin, Leong Kwai
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p. 319 - 332
(2007/10/02)
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- Studies on Ketene and Its Derivatives. CXVIII. Nickel- or Palladium-Catalyzed Reaction of Diketene with Organometallics. Synthesis of 3-Substituted 3-Butenoic Acids
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The reaction of diketene (1) with some organometallics was investigated.The reaction of 1 with benzyl Grignard reagents in the presence of nickel(II) chloride afforded 3-benzyl-3-butenoic acids 2a-e.In the presence of dichloronickel, primary alkylmagnesium bromides reacted with 1 to give 3-methylenealkanoic acids 2g-i. (E)-1-Alkenyldiisobutylaluminiums, in the presence of Pd(O)-catalyst, reacted with 1 to give 3-methylene-4-alkenoic acids 5a-c.Similarly, alkynyl- and aryl-zinc chlorides gave 3-methylene-4-alkynoic acids 7a-d and 3-aryl-3-butenoic acids 8a-c, respectively.Keywords - diketene: Grignard reagent; alkenylaluminium; alkynylzinc chloride; arylzinc chloride; palladium-catalyst; nickel-catalyst; 3-butenoic acid; 3-substituted 3-butenoic acid
- Abe, Yoshihito,Sato, Masayuki,Goto, Hiroyuki,Sugawara, Rie,Takahashi, Eri,Kato, Tetsuzo
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p. 4346 - 4354
(2007/10/02)
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