Browsing by Author "Chan, Fu-Wei"

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[3+2] Cycloaddition of Dialkyl (E)-Hex-2-en-4-ynedioates to [60]Fullerene by Phosphane-Promoted Tandem alpha(delta ')-Michael Additions
(2012-05-01)
Chuang, Shih-Ching
;
Deng, Jie-Cheng
;
Chan, Fu-Wei
;
Chen, Sheng-Yuan
;
Huang, Wei-Je
Organophosphanes promote the [3+2] cycloaddition reactions of dialkyl (E)-hex-2-en-4-ynedioates and [60]fullerene, giving a series of cyclopenteno-fullerenes 3ak bearing phosphorus ylides. This cycloaddition reaction is initiated by the attack of nucleophilic phosphanes at the a(d')-C atom of the dialkyl (E)-hex-2-en-4-ynedioate, which generates a 1,3-dipolar species. These 1,3-dipoles then react with C60 followed by intramolecular cyclization to give cyclopenteno-fullerenes in moderate-to-good yields. In a cyclic voltmmetry study, these novel fullerenes show a larger cathodic shift in their first reduction potential relative to [6,6]phenyl-C61 methyl butyrate, which indicates that these new derivatives possess higher LUMO energy levels.
Assembly of Dimethyl Acetylenedicarboxylate and Phosphanes with Aldehydes Leading to gamma-Lactones Bearing alpha-Phosphorus Ylides as Wittig Reagents
(2012-10-01)
Deng, Jie-Cheng
;
Chan, Fu-Wei
;
Kuo, Chih-Wei
;
Cheng, Chun-An
;
Huang, Chien-Yu
We report herein a convenient route to the synthesis of aryl-substituted ?-lactones bearing an a-phosphorus ylide moiety through the assembly of dimethyl acetylenedicarboxylate (DMAD), electron-deficient aldehydes, and triaryl- or trialkylphosphanes in moderate to good yields. The formation of ?-lactones is highly dependent on the reaction time, the phosphane nucleophile, and the molar ratio of DMAD, aldehyde, and phosphane. We found that reactions with a DMAD/aldehyde/tri-p-tolylphosphane molar ratio of 3:1:6 and more electron-deficient aldehydes, such as 4-nitrobenzaldehyde and 4-chloro-3-nitrobenzaldehyde, gave good yields. The isolated ylides reacted with aldehydes as Wittig reagents to give olefins in moderate yields.
Palladium-Catalyzed and Hybrid Acids-Assisted Synthesis of [60]Fulleroazepines in One Pot under Mild Conditions: Annulation of N-Sulfonyl-2-aminobiaryls with [60]Fullerene through Sequential C-H Bond Activation, C-C and C-N Bond Formation
(2012-09-01)
Rajeshkumar, Venkatachalam
;
Chan, Fu-Wei
;
Chuang, Shih-Ching
;
應用化學系
;
Department of Applied Chemistry
An extraordinarily efficient hybrid acids-assisted, palladium-catalyzed and chelating-group-assisted C?H bond activation of N-sulfonyl-2-aminobiaryls and their annulations with [60]fullerene via sequential C?C and C?N bond formation at room temperature to afford [60]fulleroazepines is demonstrated. The formation of [60]fulleroazepines is highly regioselective and tolerant to both electron-withdrawing and electron-donating groups on the aryl moiety and the reaction gives monofunctionalized fullerenes in good yields (up to 54% isolated yield and 92% based on converted C60).
Palladium-Catalyzed Regio- and Stereoselective Hydrosulfonation of Propiolate Esters
(2017-11-01)
Raju, Selvam
;
Annamalai, Pratheepkumar
;
Chan, Fu-Wei
;
Tseng, Po-Yen
;
Chen, Po-Yen
An efficient palladium-catalyzed addition reaction of alkyland arylsulfonic acids to propiolate esters to yield alkenyl sulfonates is demonstrated. The formation of alkenyl sulfonates is highly regio- and stereoselective with favorable yields of up to 95%, and two of the alkenyl sulfonates are utilized for a Sonogashira cross-coupling reaction to produce (Z)-1,3-enynoates.