Fuk Yee Kwong

Name:

Organization: The Hong Kong Polytechnic University

Department: State Key Laboratory of Chirosciences and Department of Applied Biology and Chemical Technology

Title:

Chemicals
References

An efficient palladium–benzimidazolyl phosphine complex for the Suzuki–Miyaura coupling of aryl mesylates: facile ligand synthesis and metal complex characterization

Co-reporter:Kin Ho Chung, Chau Ming So, Shun Man Wong, Chi Him Luk, Zhongyuan Zhou, Chak Po Lau and Fuk Yee Kwong

Chemical Communications 2012 vol. 48(Issue 14) pp:1967-1969

Publication Date(Web):11 Jan 2012

DOI:10.1039/C2CC15972D

A new class of easily accessible hemilabile benzimidazolyl phosphine ligands has been developed. The ligand skeleton is prepared from commercially available and inexpensive o-phenylenediamine and 2-bromobenzoic acid. With catalyst loading down to 0.5 mol% palladium, excellent catalytic activity towards the Suzuki–Miyaura coupling of aryl mesylates is still observed. This represents the lowest catalyst loading achieved so far for this reaction in general. X-Ray crystallography shows that new ligand L2 is coordinated with Pd in a κ2-P,N fashion.

An Efficient Class of P,N-Type PhMezole-phos Ligands: Applications in Palladium-Catalyzed Suzuki Coupling of Aryl Chlorides

Co-reporter:Shun Man Wong;Chau Ming So;Kin Ho Chung;Chak Po Lau

European Journal of Organic Chemistry 2012 Volume 2012( Issue 22) pp:4172-4177

Publication Date(Web):

DOI:10.1002/ejoc.201200355

Abstract

This study describes an efficient class of hemilabile benzimidazolyl–phosphane ligands that can be easily accessed from commercially available and inexpensive starting materials. The application of this ligand array in the palladium-catalyzed Suzuki–Miyaura coupling reaction of aryl chlorides with arylboronic acids is described. The palladium catalyst generated from this hemilabile phosphane is highly effective in the Suzuki–Miyaura coupling of unactivated aryl chlorides, and catalyst loadings as low as 1 ppm can be achieved.

P,N-Type benzimidazolyl phosphine ligands for the palladium-catalyzed Suzuki coupling of potassium aryltrifluoroborates and aryl chlorides

Co-reporter:Shun Man Wong, Chau Ming So, Kin Ho Chung, Chi Him Luk, Chak Po Lau, Fuk Yee Kwong

Tetrahedron Letters 2012 Volume 53(Issue 29) pp:3754-3757

Publication Date(Web):18 July 2012

DOI:10.1016/j.tetlet.2012.05.017

This study describes the efficacy of P,N-type benzimidazolyl phosphine ligands, which can be easily synthesized from commercially available and inexpensive starting materials. The application of this ligand array in palladium-catalyzed Suzuki–Miyaura coupling reaction of aryl chlorides with potassium aryltrifluoroborates is described. The air stable benzimidazolyl phosphines in combination with a palladium metal precursor provides highly effective catalysts for the Suzuki–Miyaura coupling of unactivated aryl chlorides and can achieve a catalyst loading of only 0.05 mol %.

Catalyst-free aza-Michael addition of azole to β,γ-unsaturated-α-keto ester: an efficient access to C–N bond formation

Co-reporter:Jun Wang, Peng-Fei Li, Sau Hing Chan, Albert S.C. Chan, Fuk Yee Kwong

Tetrahedron Letters 2012 Volume 53(Issue 23) pp:2887-2889

Publication Date(Web):6 June 2012

DOI:10.1016/j.tetlet.2012.03.132

An efficient aza-Michael addition of azoles to β,γ-unsaturated-α-keto esters under room temperature conditions has been developed. In this conjugate addition, no additional catalyst is employed. Azole reacts with β,γ-unsaturated-α-keto ester smoothly to afford new C–N bond adducts in good to excellent yields (up to 96%).

Asymmetric Hydroalkynylation of Norbornadienes Promoted by Chiral Iridium Catalysts

Co-reporter:Dr. Bao-Min Fan;Qing-jing Yang;Jun Hu;Cai-ling Fan;Si-feng Li;Lu Yu;Dr. Chao Huang;Wing Wai Tsang;Dr. Fuk Yee Kwong

Angewandte Chemie International Edition 2012 Volume 51( Issue 31) pp:7821-7824

Publication Date(Web):

DOI:10.1002/anie.201203107

Carbon–Boron Bond Cross-Coupling Reaction Catalyzed by −PPh2 Containing Palladium–Indolylphosphine Complexes

Co-reporter:Wing Kin Chow, On Ying Yuen, Chau Ming So, Wing Tak Wong, and Fuk Yee Kwong

The Journal of Organic Chemistry 2012 Volume 77(Issue 7) pp:3543-3548

Publication Date(Web):March 13, 2012

DOI:10.1021/jo202472k

This study describes the application of indolylphosphine ligands with a diphenylphosphino moiety to the palladium-catalyzed borylation of aryl chlorides. The combination of palladium metal precursor with PPh2-Andole-phos, which comprises an inexpensive −PPh2 group, provides highly effective catalysts for the borylation of aryl chlorides. A range of functional groups such as −CN, −NO2, −CHO, −COMe, −COOMe, and −CF3 was compatible, and the catalyst loading down to 0.025 mol % of Pd can be achieved. The Pd/PPh2-Andole-phos system is able to catalyze both borylation reaction and Suzuki–Miyaura coupling reaction in a one-pot sequential manner for the direct synthesis of biaryl compounds in excellent yields.

Advances and Applications in Organocatalytic Asymmetric aza-Michael Addition

Co-reporter:Dr. Jun Wang;Dr. Pengfei Li;Pui Ying Choy;Dr. Albert S. C. Chan;Dr. Fuk Yee Kwong

ChemCatChem 2012 Volume 4( Issue 7) pp:917-925

Publication Date(Web):

DOI:10.1002/cctc.201200135

Advances and Applications in Organocatalytic Asymmetric aza-Michael Addition

Co-reporter:Dr. Jun Wang;Dr. Pengfei Li;Pui Ying Choy;Dr. Albert S. C. Chan;Dr. Fuk Yee Kwong

ChemCatChem 2012 Volume 4( Issue 7) pp:

Publication Date(Web):

DOI:10.1002/cctc.201290025

Palladium-catalyzed cross-coupling reactions of aryl mesylates

Co-reporter:Chau Ming So and Fuk Yee Kwong

Chemical Society Reviews 2011 vol. 40(Issue 10) pp:4963-4972

Publication Date(Web):22 Aug 2011

DOI:10.1039/C1CS15114B

Palladium-catalyzed cross-coupling reactions are state-of-the art methods for synthesis of many important compounds. The development of the use of the phenol-derived sulfonated hydroxyl group in the coupling reactions is highly attractive as the hydroxyl group is commonly present in organic compounds and they are versatile alternatives to aryl halides in cross-coupling reactions. In this tutorial review, we summarize the current development of palladium-catalyzed cross-coupling reactions of aryl mesylates.

A versatile palladium catalyst system for Suzuki–Miyaura coupling of alkenyl tosylates and mesylates

Co-reporter:Pui Yu Wong, Wing Kin Chow, Kin Ho Chung, Chau Ming So, Chak Po Lau and Fuk Yee Kwong

Chemical Communications 2011 vol. 47(Issue 29) pp:8328-8330

Publication Date(Web):17 Jun 2011

DOI:10.1039/C1CC12240A

A general and effective palladium system for Suzuki–Miyaura coupling of alkenyl electrophiles under mild reaction conditions is reported. With the Pd(OAc)2/CM-phos system, a variety of alkenyl tosylates are coupled well with ArB(OH)2. Moreover, the first successful examples of using alkenyl mesylates in alkenylation are also described.

Highly efficient carbazolyl-derived phosphine ligands: application to sterically hindered biaryl couplings

Co-reporter:Sheung Chun To and Fuk Yee Kwong

Chemical Communications 2011 vol. 47(Issue 17) pp:5079-5081

Publication Date(Web):29 Mar 2011

DOI:10.1039/C1CC10708A

A new family of phosphine ligands bearing a bulky carbazolyl scaffold is described. With the combination of ligand 2a and Pd(OAc)2, difficult tri-ortho-substituted biaryl couplings are accomplished smoothly. In particular, the catalyst loading as low as 0.02 mol% of Pd for non-activated 2,6-disubstituted aryl chloride coupling can be achieved.

Palladium-Catalyzed Oxidative C–H Bond Coupling of Steered Acetanilides and Aldehydes: A Facile Access to ortho-Acylacetanilides

Co-reporter:Yinuo Wu, Baozhu Li, Fei Mao, Xingshu Li, and Fuk Yee Kwong

Organic Letters 2011 Volume 13(Issue 12) pp:3258-3261

Publication Date(Web):May 20, 2011

DOI:10.1021/ol201201a

A palladium-catalyzed oxidative C–H bond functionalization/ortho-acylation of acetanilides using easily accessible aldehyde as the acyl source is described. In the presence of a Pd(TFA)2 catalyst and tert-butylhydroperoxide at 90 °C in general, an array of ortho-acylacetanilides can be afforded in good yields.

Organocatalytic Asymmetric Aldol Reaction of Ketones with ,-Unsaturated -Keto Esters: An Efficient Access to Chiral Tertiary Alcohol Skeletons

Co-reporter:Pengfei Li;Sau Hing Chan;Albert S. C. Chan

Advanced Synthesis & Catalysis 2011 Volume 353( Issue 7) pp:1179-1184

Publication Date(Web):

DOI:10.1002/adsc.201000982

Abstract

This update describes a highly efficient organocatalytic aldol reaction of ketones and β,γ-unsaturated α-keto esters for constructing the chiral tertiary alcohol motif. With the application of 9-amino(9-deoxy)epi-Cinchona alkaloid and an acidic additive as catalysts, both acyclic and cyclic ketones react with β,γ-unsaturated α-keto esters smoothly to afford aldol adducts in good to excellent yields and asymmetric induction. This protocol offers a new pathway for the construction of adjacent chiral carbon centers and the synthesis of chiral β-hydroxy carbonyl compounds.

Organocatalytic asymmetric Michael-type reaction between β,γ-unsaturated α-keto ester and α-nitro ketone

Co-reporter:Pengfei Li, Sau Hing Chan, Albert S. C. Chan and Fuk Yee Kwong

Organic & Biomolecular Chemistry 2011 vol. 9(Issue 23) pp:7997-7999

Publication Date(Web):16 Sep 2011

DOI:10.1039/C1OB06191G

A Michael-type reaction of β,γ-unsaturated α-keto ester and α-nitro ketone was established. With a thiourea catalyst derived from cinchona alkaloid, the reactions afford products in 47–94% yields with 68–96% ee.

Efficient cyanation of aryl bromides with K4[Fe(CN)6] catalyzed by a palladium-indolylphosphine complex

Co-reporter:Pui Yee Yeung, Chun Pui Tsang, Fuk Yee Kwong

Tetrahedron Letters 2011 Volume 52(Issue 52) pp:7038-7041

Publication Date(Web):28 December 2011

DOI:10.1016/j.tetlet.2011.09.088

This study describes a general palladium-catalyzed cyanation of aryl bromides using K4[Fe(CN)6] as the cyanide surrogate. The reactions can be successfully conducted under mild reaction conditions (at 50 °C) in mixed solvents (water/MeCN = 1:1) without any surfactant additives, and afford the desired aryl nitriles in good-to-excellent yields. Particularly noteworthy is that this system allows the mildest reaction temperature reported so far for palladium-catalyzed cyanation of aryl bromides with K4[Fe(CN)6] source in general. Common functional groups, including keto, aldehyde, free amine, and heterocyclic substrates are compatible under this system. Interestingly, the phosphine ligands bearing –PCy2 moiety, which usually show excellent activity in aryl halide couplings, are found less effective than the corresponding ligands with –PPh2 group.

Palladium-Catalyzed Borylation of Aryl Mesylates and Tosylates and Their Applications in One-Pot Sequential SuzukiMiyaura Biaryl Synthesis

Co-reporter:Wing Kin Chow;Dr. Chau Ming So;Dr. Chak Po Lau ;Dr. Fuk Yee Kwong

Chemistry - A European Journal 2011 Volume 17( Issue 25) pp:6913-6917

Publication Date(Web):

DOI:10.1002/chem.201100361

Palladium-Catalyzed Direct Arylation of Heteroarenes with Aryl Mesylates

Co-reporter:Dr. Chau Ming So;Dr. Chak Po Lau ;Dr. Fuk Yee Kwong

Chemistry - A European Journal 2011 Volume 17( Issue 3) pp:761-765

Publication Date(Web):

DOI:10.1002/chem.201002354

Organocatalysis in Cross-Coupling: DMEDA-Catalyzed Direct C−H Arylation of Unactivated Benzene

Co-reporter:Wei Liu ; Hao Cao ; Hua Zhang ; Heng Zhang ; Kin Ho Chung ; Chuan He ; Haibo Wang ; Fuk Yee Kwong ;Aiwen Lei

Journal of the American Chemical Society 2010 Volume 132(Issue 47) pp:16737-16740

Publication Date(Web):August 2, 2010

DOI:10.1021/ja103050x

A striking breakthrough to the frame of traditional cross-couplings/C−H functionalizations using an organocatalyst remains unprecedented. We uncovered a conceptually different approach toward the biaryl syntheses by using DMEDA as the catalyst to promote the direct C−H arylation of unactivated benzene in the presence of potassium tert-butoxide. The arylation of unactivated benzene with aryl iodides, or aryl bromides and even chlorides under the assistance of an iodo-group, could simply take place at 80 °C. The new methodology presumably involves an aryl radical anion as an intermediate. This finding offers an option toward establishing a new horizon for direct C−H/cross-coupling reactions.

Highly Enantioselective and Efficient Organocatalytic Aldol Reaction of Acetone and β,γ-Unsaturated α-Keto Ester

Co-reporter:Pengfei Li, Junling Zhao, Fengbo Li, Albert S. C. Chan, and Fuk Yee Kwong

Organic Letters 2010 Volume 12(Issue 24) pp:5616-5619

Publication Date(Web):November 11, 2010

DOI:10.1021/ol102254q

An effective organocatalytic asymmetric aldol reaction of acetone to β,γ-unsaturated α-keto ester has been developed. In the presence of 5 mol % of 9-amino (9-deoxy)-epicinchona alkaloid and 10 mol % of 4-nitrobenzoic acid, the aldol adducts containing a chiral tertiary alcohol moiety were obtained in excellent yields and enantioselectivities.

Recent developments on chiral P,S-type ligands and their applications in asymmetric catalysis

Co-reporter:Fuk Loi Lam, Fuk Yee Kwong and Albert S. C. Chan

Chemical Communications 2010 vol. 46(Issue 26) pp:4649-4667

Publication Date(Web):24 May 2010

DOI:10.1039/C000207K

This feature article illustrates new concepts and approaches for designing new P,S-mixed donor chelating ligands based on three major types of chiral skeleton, the central, axial and planar chirality. The versatility in structural modification is highlighted. It offers an effective pathway to access scientifically useful chiral ligands of diverse electronic and steric properties for optimization in various catalytic enantioselective transformations. In this article, the applications of these optically active ligands in a variety of asymmetric catalytic reactions will be discussed with reference to updated literature findings as well as the author's original research.

A Decade of Advancements in PausonKhand-Type Reactions

Co-reporter:Hang-Wai Lee ;Fuk-Yee Kwong

European Journal of Organic Chemistry 2010 Volume 2010( Issue 5) pp:789-811

Publication Date(Web):

DOI:10.1002/ejoc.200900892

Abstract

This Microreview illustrates the conceptual evolution ofPauson–Khand-type reactions and the recent advancements in catalyst design and applications. Intra- and intermolecular Pauson–Khand-type reactions, as well as their enantioselective versions, are reviewed. In addition to previous reviews, this article mainly covers literature references on the developments between the late 1990s and early 2009.

Asymmetric hydrogenation of aromatic ketones using new chiral-bridged diphosphine/diamine–Ru(II) complexes

Co-reporter:Yu Ming Cui, Lai Lai Wang, Fuk Yee Kwong, Wei Sun

Chinese Chemical Letters 2010 Volume 21(Issue 12) pp:1403-1406

Publication Date(Web):December 2010

DOI:10.1016/j.cclet.2010.05.027

A series of chiral secondary alcohols were easily prepared by means of asymmetric hydrogenation of prochiral aromatic ketones using a new ((Rax)-BuP)/(R,R)-DPEN–Ru(II) complex catalyst system. The hydrogenation of 2-methylacetophenone in n-butanol (t-BuOK/Ru = 45.6/1, S/C = 500, 20 atm. of H2, 20 °C, 48 h) afforded (S)-1-(2′-methylphenyl)ethanol in 92% ee and >99% conversion.

Remarkably Effective Phosphanes Simply with a PPh2 Moiety: Application to Pd-Catalysed Cross-Coupling Reactions for Tetra-ortho-substituted Biaryl Syntheses

Co-reporter:ChauMing So;WingKin Chow;PuiYing Choy;ChakPo Lau Dr. ;FukYee Kwong Dr.

Chemistry - A European Journal 2010 Volume 16( Issue 27) pp:7996-8001

Publication Date(Web):

DOI:10.1002/chem.201000723

Palladium-Catalyzed Sonogashira Coupling of Aryl Mesylates and Tosylates

Co-reporter:PuiYing Choy;WingKin Chow;ChauMing So;ChakPo Lau Dr. ;FukYee Kwong Dr.

Chemistry - A European Journal 2010 Volume 16( Issue 33) pp:9982-9985

Publication Date(Web):

DOI:10.1002/chem.201001269

A Mild and Efficient Palladium-Catalyzed Cyanation of Aryl Mesylates in Water or tBuOH/Water

Co-reporter:Pui Yee Yeung;Dr. Chau Ming So;Dr. Chak Po Lau ;Dr. Fuk Yee Kwong

Angewandte Chemie International Edition 2010 Volume 49( Issue 47) pp:8918-8922

Publication Date(Web):

DOI:10.1002/anie.201005121

A Mild and Efficient Palladium-Catalyzed Cyanation of Aryl Mesylates in Water or tBuOH/Water

Co-reporter:Pui Yee Yeung;Dr. Chau Ming So;Dr. Chak Po Lau ;Dr. Fuk Yee Kwong

Angewandte Chemie 2010 Volume 122( Issue 47) pp:9102-9106

Publication Date(Web):

DOI:10.1002/ange.201005121

Palladium-Catalyzed Cross-Coupling of Aryl Halides Using Organotitanium Nucleophiles

Co-reporter:HangWai Lee;FukLoi Lam Dr.;ChauMing So;ChakPo Lau Dr.;AlbertS.C. Chan Dr.;FukYee Kwong Dr.

Angewandte Chemie 2009 Volume 121( Issue 40) pp:7572-7575

Publication Date(Web):

DOI:10.1002/ange.200904033

Iron complex-catalyzed N-arylation of pyrazoles under aqueous medium

Co-reporter:Hang Wai Lee, Albert S.C. Chan, Fuk Yee Kwong

Tetrahedron Letters 2009 50(42) pp: 5868-5871

Publication Date(Web):

DOI:10.1016/j.tetlet.2009.08.018

Palladium-Catalyzed Cross-Coupling of Aryl Halides Using Organotitanium Nucleophiles

Co-reporter:HangWai Lee;FukLoi Lam Dr.;ChauMing So;ChakPo Lau Dr.;AlbertS.C. Chan Dr.;FukYee Kwong Dr.

Angewandte Chemie International Edition 2009 Volume 48( Issue 40) pp:7436-7439

Publication Date(Web):

DOI:10.1002/anie.200904033

Microwave-Assisted Rhodium-Complex-Catalyzed Cascade Decarbonylation and Asymmetric PausonKhand-Type Cyclizations

Co-reporter:Hang Wai Lee;Lai Na Lee;Albert S. C. Chan

European Journal of Organic Chemistry 2008 Volume 2008( Issue 19) pp:3403-3406

Publication Date(Web):

DOI:10.1002/ejoc.200800272

Abstract

Microwave-assisted Rh–diphosphane-complex-catalyzed dual catalysis is reported. This cooperative process provides [2+2+1] cycloadducts by sequential decarbonylation of aldehyde or formate and carbonylation of enynes within a short period of time. Various O-, N-, and C-tethered enynes were transformed into the corresponding products in good yields. The first enantioselective version of this microwave-accelerated cascade cyclization was realized. In the presence of chiral Rh-(S)-bisbenzodioxanPhos complex, the cyclopentenone products were achieved with ee values up to 90 %. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

Palladium-Catalyzed Amination of Aryl Mesylates

Co-reporter:ChauMing So;Zhongyuan Zhou Dr.;ChakPo Lau Dr. ;FukYee Kwong Dr.

Angewandte Chemie 2008 Volume 120( Issue 34) pp:6502-6506

Publication Date(Web):

DOI:10.1002/ange.200802157

A General Palladium-Catalyzed SuzukiMiyaura Coupling of Aryl Mesylates

Co-reporter:ChauMing So;ChakPo Lau Dr. ;FukYee Kwong Dr.

Angewandte Chemie 2008 Volume 120( Issue 42) pp:8179-8183

Publication Date(Web):

DOI:10.1002/ange.200803193

A General Palladium-Catalyzed SuzukiMiyaura Coupling of Aryl Mesylates

Co-reporter:ChauMing So;ChakPo Lau Dr. ;FukYee Kwong Dr.

Angewandte Chemie International Edition 2008 Volume 47( Issue 42) pp:8059-8063

Publication Date(Web):

DOI:10.1002/anie.200803193

Palladium-Catalyzed Amination of Aryl Mesylates

Co-reporter:ChauMing So;Zhongyuan Zhou Dr.;ChakPo Lau Dr. ;FukYee Kwong Dr.

Angewandte Chemie International Edition 2008 Volume 47( Issue 34) pp:6402-6406

Publication Date(Web):

DOI:10.1002/anie.200802157

Formate as a CO surrogate for cascade processes: Rh-catalyzed cooperative decarbonylation and asymmetric Pauson–Khand-type cyclization reactions

Co-reporter:Hang Wai Lee, Albert S. C. Chan and Fuk Yee Kwong

Chemical Communications 2007 (Issue 25) pp:2633-2635

Publication Date(Web):30 Mar 2007

DOI:10.1039/B702718D

A rhodium-(S)-xyl-BINAP complex-catalyzed tandem formate decarbonylation and [2 + 2 + 1] carbonylative cyclization is described; this cooperative process utilizes formate as a condensed CO source, and the newly developed cascade protocol can be extended to its enantioselective version, providing up to 94% ee of the cyclopentenone adducts.

Easily Accessible Benzamide-Derived P,O Ligands (Bphos) for Palladium-Catalyzed Carbon–Nitrogen Bond-Forming Reactions

Co-reporter:Guoshu Chen Dr.;Hang Wai Lee Dr.;Wai Har Lam Dr.;Wai Shan Fok

Chemistry – An Asian Journal 2007 Volume 2(Issue 2) pp:306-313

Publication Date(Web):29 JAN 2007

DOI:10.1002/asia.200600322

Easily accessible benzamide-derived hemilabile phosphine ligands were efficiently prepared through ortho-directed lithiation of the corresponding N,N-diethylbenzamide followed by quenching with chlorodialkylphosphines. These structurally simple hemilabile ligands were found to be highly effective in palladium-catalyzed amination of aryl and heteroaryl chlorides. Various sterically congested and functionalized aryl halide substrates were compatible in these reaction conditions. By using optimized reaction conditions, remarkable catalyst productivity (total turnover number up to 8400) was obtained.

Nickel-catalyzed asymmetric α-arylation of ketone enolates

Co-reporter:Guoshu Chen, Fuk Yee Kwong, Hoi On Chan, Wing-Yiu Yu and Albert S. C. Chan

Chemical Communications 2006 (Issue 13) pp:1413-1415

Publication Date(Web):21 Feb 2006

DOI:10.1039/B601691J

An atropisomeric dipyridyldiphosphine, P-Phos, can effect highly enantioselective Ni-catalyzed α-arylation of ketone enolates with aryl halides to install an all-carbon quaternary stereogenic center in up to 98% ee and excellent yields.

Iridium-catalyzed cascade decarbonylation/highly enantioselective Pauson–Khand-type cyclization reactions

Co-reporter:Fuk Yee Kwong, Hang Wai Lee, Wai Har Lam, Liqin Qiu, Albert S.C. Chan

Tetrahedron: Asymmetry 2006 Volume 17(Issue 8) pp:1238-1252

Publication Date(Web):18 April 2006

DOI:10.1016/j.tetasy.2006.03.036

An easily accessible chiral iridium-BINAP complex can effect the cooperative processes of decarbonylation of an aldehyde and cascaded enantioselective Pauson–Khand-type reaction. A survey of ligands revealed that atropisomeric aryl-diphosphine ligands were superior to chiral alkyl-diphosphines in this dual catalysis. Applying the reaction conditions of [IrCl(COD)]2/(S)-BINAP complex with nonylaldehyde as a CO surrogate at 100 °C in anhydrous dioxane solvent, various 1,6-enynes were transformed to the corresponding optically active bicyclic cyclopentenones with excellent enantioselectivities (up to 98% ee).2-(3-Methoxyphenyl)-7-oxabicyclo[3.3.0]oct-1-en-3oneC14H14O3[α]D25=+26.3 (c 0.11, CH2Cl2)2-(4-Methylphenyl)-7-oxabicyclo[3.3.0]oct-1-en-3oneC14H14O2[α]D25=+60.9 (c 0.10, CH2Cl2)

Rhodium-BisbenzodioxanPhos Complex-Catalyzed Homogeneous Enantioselective Pauson–Khand-Type Cyclization in Alcoholic Solvents

Co-reporter:Fuk Yee Kwong;Hang Wai Lee;Liqin Qiu;Wai Har Lam;Yue-Ming Li;Hoi Lun Kwong;Albert S. C. Chan

Advanced Synthesis & Catalysis 2005 Volume 347(Issue 14) pp:

Publication Date(Web):15 NOV 2005

DOI:10.1002/adsc.200505105

The chiral atropisomeric diphosphane ligand (S)-BisbenzodioxanPhos was found to be highly effective in the co-operative processeses of aldehyde decarbonylation and cascaded enantioselective Pauson–Khand-type reactions. Various 1,6-enynes were transformed to the corresponding bicyclic cyclopentenones in good yields and enantiomeric excesses (up to 96% ee). The attractive feature of this new Rh-catalyzed homogeneous dual catalysis system is that the reaction can be performed in alcoholic solution.

Rhodium-Catalyzed Asymmetric Aqueous Pauson–Khand-Type Reaction

Co-reporter:Fuk Yee Kwong Dr.;Yue Ming Li Dr.;Wai Har Lam Dr.;Liqin Qiu Dr.;Hang Wai Lee;Chi Hung Yeung Dr.;Kin Shing Chan Dr.;Albert S. C. Chan Dr.

Chemistry - A European Journal 2005 Volume 11(Issue 13) pp:

Publication Date(Web):13 APR 2005

DOI:10.1002/chem.200401237

An interesting rhodium-catalyzed asymmetric aqueous Pauson–Khand-type reaction was developed. A chiral atropisomeric dipyridyldiphosphane ligand was found to be highly effective in this system. This operationally simple protocol allows both catalyst and reactants to be handled under air without precautions. Various enynes were transformed to the corresponding bicyclic cyclopentenones in good yield and enantiomeric excess (up to 95 % ee). A study of the electronic effects of the enyne substrates revealed a correlation between the electronic properties of the substrates and the ee value obtained in the product of the Pauson–Khand-type reaction. A linear free-energy relationship was observed from a Hammett study.

A simple and highly efficient P,O-type ligand for Suzuki–Miyaura cross-coupling of aryl halides

Co-reporter:Fuk Yee Kwong, Wai Har Lam, Chi Hung Yeung, Kin Shing Chan and Albert S. C. Chan

Chemical Communications 2004 (Issue 17) pp:1922-1923

Publication Date(Web):28 Jul 2004

DOI:10.1039/B407243J

A simple and efficient hemilabile-type phosphine ligand, found to be highly effective in Suzuki–Miyaura cross-coupling of aryl chlorides with generally low Pd-catalyst loading (0.05%), was prepared in one step based on an economically attractive approach from commercially available benzamide starting material.

An active ferrocenyl triarylphosphine for palladium-catalyzed Suzuki–Miyaura cross-coupling of aryl halides

Co-reporter:Fuk Yee Kwong, Kin Shing Chan, Chi Hung Yeung and Albert S. C. Chan

Chemical Communications 2004 (Issue 20) pp:2336-2337

Publication Date(Web):21 Sep 2004

DOI:10.1039/B407661C

Pd-catalyzed Suzuki–Miyaura reaction of aryl chlorides was accomplished through the use of an active ferrocene-based triarylphosphine ligand. This air- and moisture-stable ligand was found to be effective for the cross-coupling of aryl halides at room temperature to 115 °C.

A versatile palladium catalyst system for Suzuki–Miyaura coupling of alkenyl tosylates and mesylates

Co-reporter:Pui Yu Wong, Wing Kin Chow, Kin Ho Chung, Chau Ming So, Chak Po Lau and Fuk Yee Kwong

Chemical Communications 2011 - vol. 47(Issue 29) pp:NaN8330-8330

Publication Date(Web):2011/06/17

DOI:10.1039/C1CC12240A

An efficient palladium–benzimidazolyl phosphine complex for the Suzuki–Miyaura coupling of aryl mesylates: facile ligand synthesis and metal complex characterization

Co-reporter:Kin Ho Chung, Chau Ming So, Shun Man Wong, Chi Him Luk, Zhongyuan Zhou, Chak Po Lau and Fuk Yee Kwong

Chemical Communications 2012 - vol. 48(Issue 14) pp:NaN1969-1969

Publication Date(Web):2012/01/11

DOI:10.1039/C2CC15972D

Recent developments on chiral P,S-type ligands and their applications in asymmetric catalysis

Co-reporter:Fuk Loi Lam, Fuk Yee Kwong and Albert S. C. Chan