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Wing-yiu Yu

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Organization: The Hong Kong Polytechnic University
Department: State Key Laboratory of Chirosciences, Department of Applied Biology and Chemical Technology
Title:
Rhodium(III)-Catalyzed Intermolecular Direct Amination of Aromatic C–H Bonds with N-Chloroamines
Co-reporter:Ka-Ho Ng, Zhongyuan Zhou, and Wing-Yiu Yu
Organic Letters 2012 Volume 14(Issue 1) pp:272-275
Publication Date(Web):December 13, 2011
DOI:10.1021/ol203046n
A Rh(III)-catalyzed direct aromatic C–H amination is achieved using N-chloroamines as a reagent. Furthermore, we also developed a one-pot amination protocol involving in situ chlorination of the secondary amines. The catalytic amination operates at mild conditions with excellent functional group tolerance and regioselectivity.
Ruthenium-catalyzed intramolecular cyclization of diazo-β-ketoanilides for the synthesis of 3-alkylideneoxindoles
Co-reporter:Wai-Wing Chan, Tsz-Lung Kwong and Wing-Yiu Yu  
Organic & Biomolecular Chemistry 2012 vol. 10(Issue 18) pp:3749-3755
Publication Date(Web):06 Mar 2012
DOI:10.1039/C2OB06985G
With [Ru(p-cymene)Cl2]2 as catalyst, diazo-β-ketoanilides would undergo intramolecular carbenoid arene C–H bond functionalization to afford 3-alkylideneoxindoles in up to 92% yields. The reaction occurs under mild conditions and exhibits excellent chemoselectivity. The lack of primary KIE (kH/kD ∼ 1) suggests that the reaction should not proceed by rate-limiting C–H bond cleavage; a mechanism involving cyclopropanation of the arene is proposed.
Palladium(II)-Catalyzed Direct ortho-CH Acylation of Anilides by Oxidative Cross-Coupling with Aldehydes using tert-Butyl Hydroperoxide as Oxidant
Co-reporter:Chun-Wo Chan;Zhongyuan Zhou
Advanced Synthesis & Catalysis 2011 Volume 353( Issue 16) pp:2999-3006
Publication Date(Web):
DOI:10.1002/adsc.201100472

Abstract

An efficient palladium-catalyzed CH acylation with aldehydes using tert-butyl hydroperoxide (TBHP) transforms various anilides into synthetically useful 2-aminobenzophenone derivatives under mild conditions (40 °C, 3 h). The acylation reaction exhibits excellent regioselectivity and functional group tolerance, and simple aromatic aldehydes, functionalized aliphatic aldehydes and heteroaromatic aldehydes are effective coupling partners. The acylation reaction is probably initiated by a rate-limiting electrophilic CH cyclopalladation (kH/kD=3.6; ρ+=−0.74) to form an arylpalladium complex, followed by acyl radical functionalization.

Pd-Catalyzed Intermolecular ortho-C−H Amidation of Anilides by N-Nosyloxycarbamate
Co-reporter:Ka-Ho Ng ; Albert S. C. Chan
Journal of the American Chemical Society 2010 Volume 132(Issue 37) pp:12862-12864
Publication Date(Web):August 25, 2010
DOI:10.1021/ja106364r
A palladium-catalyzed ortho-C−H amidation of anilides by N-nosyloxycarbamates was developed for the synthesis of 2-aminoanilines. This reaction can be carried out under relatively mild conditions and exhibits excellent regioselectivity and functional group tolerance. The amidation reaction is probably initiated by rate-limiting C−H cyclopalladation (kH/kD = 3.7) to form an arylpalladium complex, followed by nitrene functionalization.
Palladium-Catalyzed Oxidative Cross-Coupling Reaction of Arylboronic Acids with Diazoesters for Stereoselective Synthesis of (E)-α,β-Diarylacrylates
Co-reporter:Yuk-Tai Tsoi, Zhongyuan Zhou, Albert S. C. Chan, and Wing-Yiu Yu
Organic Letters 2010 Volume 12(Issue 20) pp:4506-4509
Publication Date(Web):September 15, 2010
DOI:10.1021/ol101796t
A Pd-catalyzed oxidative cross-coupling reaction of arylboronic acids with α-diazoesters was achieved using molecular oxygen as the sole reoxidant, and E-α,β-diarylacrylates were obtained in good yields and >20:1 E-to-Z selectivity.
Pd-Catalyzed Ortho-C−H Acylation/Cross Coupling of Aryl Ketone O-Methyl Oximes with Aldehydes Using tert-Butyl Hydroperoxide as Oxidant
Co-reporter:Chun-Wo Chan, Zhongyuan Zhou, Albert S. C. Chan and Wing-Yiu Yu
Organic Letters 2010 Volume 12(Issue 17) pp:3926-3929
Publication Date(Web):August 12, 2010
DOI:10.1021/ol101618u
A Pd-catalyzed protocol for direct C−H bond acylation by cross coupling of aryl ketone oximes and aldehydes using tert-butyl hydroperoxide (TBHP) as oxidant was developed. With oximes as a directing group for the C−H activation, the coupling with aldehydes was achieved with remarkable regioselectivity. The acylation reactions exhibit excellent functional group tolerance, and both aliphatic and heteroaromatic aldehydes can be effectively coupled to the oximes.
Palladium-Catalyzed Decarboxylative Arylation of C−H Bonds by Aryl Acylperoxides
Co-reporter:Wing-Yiu Yu, Wing Nga Sit, Zhongyuan Zhou and Albert S.-C. Chan
Organic Letters 2009 Volume 11(Issue 15) pp:3174-3177
Publication Date(Web):July 7, 2009
DOI:10.1021/ol900756g
A Pd(OAc)2-catalyzed protocol for decarboxylative arylation of aromatic C−H bond was developed using aryl acylperoxides as inexpensive aryl sources. Substrates containing pyridyl, oxime, and oxazoline groups undergo effectively ortho-selective C−H arylation with excellent functional group tolerance. This arylation should begin by directing-group-assisted cyclopalladation, followed by the reaction of the palladacycle with aryl radicals generated in situ by thermal decomposition of the peroxides.
Ruthenium-catalyzed intramolecular cyclization of diazo-β-ketoanilides for the synthesis of 3-alkylideneoxindoles
Co-reporter:Wai-Wing Chan, Tsz-Lung Kwong and Wing-Yiu Yu
Organic & Biomolecular Chemistry 2012 - vol. 10(Issue 18) pp:NaN3755-3755
Publication Date(Web):2012/03/06
DOI:10.1039/C2OB06985G
With [Ru(p-cymene)Cl2]2 as catalyst, diazo-β-ketoanilides would undergo intramolecular carbenoid arene C–H bond functionalization to afford 3-alkylideneoxindoles in up to 92% yields. The reaction occurs under mild conditions and exhibits excellent chemoselectivity. The lack of primary KIE (kH/kD ∼ 1) suggests that the reaction should not proceed by rate-limiting C–H bond cleavage; a mechanism involving cyclopropanation of the arene is proposed.
2-Propenamide, N-(4-bromophenyl)-N,2-dimethyl-
2-Propenamide, N-(4-bromophenyl)-N,2-dimethyl-
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2-Propenamide, N-(4-bromophenyl)-N,2-dimethyl-
2-Propenamide, N-(4-fluorophenyl)-N,2-dimethyl-
2-Propenamide, N-(4-fluorophenyl)-N,2-dimethyl-
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2-Propenamide, N-(4-fluorophenyl)-N,2-dimethyl-
2-Propenamide, N-(4-iodophenyl)-N,2-dimethyl-
2-Propenamide, N-(4-iodophenyl)-N,2-dimethyl-
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2-Propenamide, N-(4-iodophenyl)-N,2-dimethyl-
1-Piperazinecarboxylic acid, 4-chloro-, 1,1-dimethylethyl ester
1-Piperazinecarboxylic acid, 4-chloro-, 1,1-dimethylethyl ester
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1-Piperazinecarboxylic acid, 4-chloro-, 1,1-dimethylethyl ester
Potassium 3-trifluoroboratopropionate tert-butyl ester
Potassium 3-trifluoroboratopropionate tert-butyl ester
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Potassium 3-trifluoroboratopropionate tert-butyl ester
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2-PROPENAMIDE, N-(4-ACETYLPHENYL)-N,2-DIMETHYL-
2-PROPENAMIDE, N-(4-ACETYLPHENYL)-N,2-DIMETHYL-
CAS:849835-38-7
2-PROPENAMIDE, N-(4-ACETYLPHENYL)-N,2-DIMETHYL-
BENZAMIDE, N-(ACETYLOXY)-4-METHOXY-
BENZAMIDE, N-(ACETYLOXY)-4-METHOXY-
CAS:615258-67-8
BENZAMIDE, N-(ACETYLOXY)-4-METHOXY-
1,2-Hydrazinedicarboxylic acid, 1-(4-methoxyphenyl)-, diethyl ester
1,2-Hydrazinedicarboxylic acid, 1-(4-methoxyphenyl)-, diethyl ester
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1,2-Hydrazinedicarboxylic acid, 1-(4-methoxyphenyl)-, diethyl ester
(5-METHOXYNAPHTHALEN-1-YL)BORONIC ACID
(5-METHOXYNAPHTHALEN-1-YL)BORONIC ACID
CAS:372521-88-5
(5-METHOXYNAPHTHALEN-1-YL)BORONIC ACID