17645-29-3Relevant academic research and scientific papers
Bromo Radical-Mediated Photoredox Aldehyde Decarbonylation towards Transition-Metal-Free Hydroalkylation of Acrylamides at Room Temperature
Sun, Zhaozhao,Huang, Huawen,Wang, Qiaolin,Deng, Guo-Jun
, p. 453 - 458 (2021/12/03)
Herein, we report a visible-light-mediated hydroalkylation reaction of alkenes using easily available aldehydes as alkyl sources via bromo radical-promoted photoredox decarbonylation. This protocol provides an alternative entry to C(sp3)?C(sp3) bond formation and features considerable advantages including mild and clean reaction conditions, obviation for transition-metal catalyst, and good functional group compatibility.
Stereospecific Electrophilic Fluorocyclization of α,β-Unsaturated Amides with Selectfluor
Fei, Haiyang,Fu, Yao,Jalani, Hitesh B.,Li, Guigen,Lu, Hongjian,Wu, Hongmiao,Xu, Zheyuan,Zhu, Lin
, (2020/03/30)
An efficient fluorocyclization of α,β-unsaturated amides through a formal halocyclization process is developed. The reaction proceeds under transition-metal-free conditions and leads to the formation of fluorinated oxazolidine-2,4-diones with excellent regio- and diastereoselectivity. The evaluation of the reaction mechanism based on preliminary experiments and density functional theory calculations suggests that a synergetic syn-oxo-fluorination occurs and is followed by an anti-oxo substitution reaction. The reaction opens a new window in the field of stereospecific fluorofunctionalization.
All-carbon-substituted quaternary carbon atoms in oxindoles by an aerobic palladium(II)-catalyzed ring closure onto tri- and tetrasubstituted double bonds
Schiffner, Julia A.,Oestreich, Martin
supporting information; experimental part, p. 1148 - 1154 (2011/04/15)
Oxidative palladium(II)-catalyzed cyclization of α,β-unsaturated amides derived from electron-rich anilines is reported. The aerobic ring closure of tri- and tetrasubstituted alkenes yields oxindoles with congested all-carbon-substituted quaternary carbon atoms. The ring-size selectivity is excellent. Selected unsymmetrically substituted arenes cyclize with perfect regioselectivity. Experimental evidence indicates that the mechanism is likely to involve Friedel-Crafts-type electrophilic substitution rather than direct C-H bond activation. Oxindoles are formed in an aerobic palladium(II)-catalyzed cyclization of tri- and tetrasubstituted double bonds at relatively low catalyst loading. The mechanism likelyinvolves a Friedel-Crafts-type electrophilic substitution rather than direct C-H bond activation.
Oxindole synthesis by palladium-catalysed aromatic C-H alkenylation
Ueda, Satoshi,Okada, Takahiro,Nagasawa, Hideko
supporting information; experimental part, p. 2462 - 2464 (2010/08/13)
A strategy involving palladium-catalysed aromatic C-H functionalisation/ intramolecular alkenylation provides a convenient and direct synthesis of 3-alkylideneoxindoles. In the presence of 5 mol% of PdCl2MeCN 2 and AgOCOCF3, a wide variety of N-cinnamoylanilines gave 3-alkylideneoxindoles in moderate to good yield. The Royal Society of Chemistry.
Tin for Organic Synthesis, 11. A Mild and Effective Synthesis of α,β-unsaturated Carboxamides and Sulfonamides by Electrophilic Substitution of Alkenylstannanes with Isocyanates
Niestroj, Michael,Neumann, Wilhelm P.,Thies, Olaf
, p. 1131 - 1136 (2007/10/02)
A new and effective method for the preparation of a variety of olefinic carboxamides 6a-k and N-(4-methylphenylsulfonyl)carboxamides 7a-d is described.The reaction of aryl and alkyl isocyanates 4a-c or 4-methylphenylsulfonyl isocyanate 5 with 1-alkenyltrialkylstannanes 1a-e and di-1-alkenyldibutylstannanes 2a-c in the presence of aluminium trichloride provides the corresponding N-aryl-substituted olefinic carboxamides 6a-k or the N-(4-methylphenylsulfonyl)-substituted olefinic carboxamides 7a-d in good yields.The stannyl moiety is superior to hydrogen as a leaving group and enables electrophilic ipso substitution at the vinylic system.In the case of di-1-alkenyldibutylstannanes the substitutions are also stereospecific, whereas the reactions of 1-alkenyltrialkylstannanes with isocyanates proceed with partial isomerisation. - Key Words: Electrophilic vinylic substitution / Isocyanates / α,β-Unsaturated amides, synthesis of / Carbodestannylation / Alkenylstannanes, applications of
OXIDATIVE KUPPLUNG VON 1,2-DIENEN MIT ISOCYANATEN AM LIG-NICKEL(0)-SYSTEM
Hoberg, Heinz,Suemmermann, Klaus
, p. 239 - 248 (2007/10/02)
Isocyanates undergo a 1/1 oxidative coupling reaction with 1,2-dienes and Lig-Ni0 systems to give azanickelacyclopentanones.The coupling to form the nickela complexes proceeds in such a way that the exo-methylene group is conjugated with the carbonyl group.The influence of the ligands and the temperature on the regioselectivity of the C-C coupling is reported.
