- Chemo-, regio-, and stereoselective hydroboration of conjugated enyne alcohol/amine: Facile synthesis of Z,Z-/Z,E-1,3-dien-1/2-ylboronic ester bearing hydroxyl/amino group
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Hydroboration of conjugated enyne alcohol/amine is studied by using copper salts and bis(pinacolato)diboron as pre-catalysts and boron source respectively. It is suggested that the chemo-selectivity is derived from a combined electronic influence of the heteroatoms on the substrate and the ligand on the transition metal. The regioselectivity is probably dominated mainly by electronic effect of the alkyne substituent. This study resulted in a highly selective protocol to access Z,Z-/Z,E-1,3-dien-1/2-ylboronic ester bearing hydroxyl/amino group.
- Xu, Hua-Dong,Wu, Hao,Jiang, Chun,Chen, Peng,Shen, Mei-Hua
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supporting information
p. 2915 - 2918
(2016/06/14)
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- The coupling of butylvinyltellurides with organometallic reagents catalysed by nickel complexes
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Vinylic tellurides couple efficiently with sp, sp2 and sp3 hybridised organometallic compounds (Li, MgX and Zn species) in the presence of dichloro-bis(triphenylphosphine)nickel(II) as catalyst.
- Raminelli, Cristiano,Gargalaka Jr., Jo?o,Silveira, Cláudio C.,Comasseto, Jo?o V.
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p. 8801 - 8809
(2008/02/10)
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- Assembly of conjugated enynes and substituted indoles via CuI/amino acid-catalyzed coupling of 1-alkynes with vinyl iodides and 2- bromotrifluoroacetanilides
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(Chemical Equation Presented) Cross-coupling of 1-alkynes with vinyl iodides occurs at 80°C in dioxane catalyzed by CuI/N,N-dimethylglycine to afford conjugated enynes in good to excellent yields. Heating a mixture of 2-bromotrifluoroacetanilide, 1-alkyne, 2 mol % of CuI, 6 mol % of L-proline, and K2CO3 in DMF at 80 °C leads to the formation of the corresponding indole. This conversion involves a CuI/L-proline-catalyzed coupling between aryl bromide and the 1-alkyne followed by a CuI-mediated cyclization process. An ortho-substituent effect directed by NHCOCF3 enables me reaction to proceed under these mild conditions. Both aryl acetylenes and O-protected propargyl alcohol can be applied, leading to 5-, 6-, or 7-substituted 2-aryl and protected 2-hydroxymethyl indoles in good yields. With simple aliphatic alkynes, however, lower yields were observed.
- Liu, Feng,Ma, Dawei
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p. 4844 - 4850
(2008/02/05)
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- Coupling of butyl vinyl tellurides with metal acetylides catalyzed by nickel complexes
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Z-Vinylic tellurides react with metal acetylides under nickel complexes catalysis to give Z-enynes and Z-enediynes in good yields.
- Raminelli, Cristiano,Gargalaka Jr., Jo?o,Silveira, Cláudio C.,Comasseto, Jo?o V.
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p. 4927 - 4930
(2007/10/03)
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- One-pot oxidation and Wittig olefination of alcohols using o-iodoxybenzoic acid and stable Wittig ylide
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Benylic, allylic, and propargylic alcohols, as well as diols, can be oxidized with o-iodoxybenzoic acid (IBX) in the presence of stabilized Wittig ylide to generate α,β-unsaturated ester in one pot. This is useful when the intermediate aldehydes are unsta
- Maiti,Yadav
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p. 1499 - 1506
(2007/10/03)
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- Lewis acid-promoted alkylations of arenes and 1-trimethylsilylalkynes with β-chloro-β-thiopropanoic esters
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Ethyl 3-chloro-3-(3,4-dichlorophenylthio)propanoate (8) reacted with electron-rich arenes in the presence of titanium tetrachloride to give the Friedel-Crafts products 10a-13a. Reactions of 8 with 1-trimethylsilylalkynes 14a-d were effected with aluminum chloride to afford the substitution products 15a-d. Some chemical transformations of the products are also described.
- Ishibashi,Mino,Sakata,Inada,Ikeda
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p. 1148 - 1151
(2007/10/02)
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- A Stereoselective Synthesis of Ethyl (2E,4Z)-2,4-Decadienoate: Pear Ester
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A stereoselective synthesis of ethyl (2E,4Z)-2,4-decadienoate (1) is reported from E-pent-2-en-4-yn-1-ol in five steps.
- Sharma, G.V.M.,Rajagopal, D.
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p. 633 - 636
(2007/10/02)
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- A STEREOSELECTIVE SYNTHESIS OF PEAR ESTER VIA ARSENIC YLIDE
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The paper describes a four-step synthesis of ethyl (2E,4Z)-2,4-decadienoate (pear ester) from propargyl alcohol with a 50percent total yield.It also gives the synthesis of ethyl (2E,4E)-2,4-decadienoate.In both cases arsenic ylides were used to give the satisfactory results.
- Zhengming, Li,Tiansheng, Wang,Diankun, Zhang,Zhengheng, Gao
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