Synthetic Organic Chemistry Laboratory

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Journal Publications (Refereed & International)

NTU Publications

1. “Practical Copper(I)-Catalysed Amidation of Aldehydes”, Chang, J. W. W.; Ton, T. M. U.; Tania, S.; Taylor, P. C.; Chan, P. W. H. Chem. Commun. 2010, 46, accepted.

2. “Ytterbium(III) Triflate-Catalyzed Tandem Friedel-Crafts Alkylation/Hydroarylation of Propargylic Alcohols with Phenols as an Expendient Route to Indenols”, Zhang, X.; Teo, W. T.; Chan, P. W. H. Org. Lett. 2009, 11, 21, 4990-4993.

3. “Iron(III) Chloride-Catalysed Direct Nucleophilic a-Substitution of Morita-Baylis-Hillman Alcohols with Alcohols, Arenes, 1,3-Dicarbonyl Compounds, and Thiols”, Zhang, X.; Rao, W.; Sally; Chan, P. W. H. Org. Biomol. Chem. 2009, 7, 20, 4186-4193 (featured as the inside front cover by invitation from the editor and reviewers).

4. “Gold-Catalyzed Intramolecular Allylic Amination of 2-Tosylaminophenylprop-1-en-3-ols. A Concise Synthesis of (±)-Angustureine”, Kothandaraman, P.; Foo, S. J.; Chan, P. W. H. J. Org. Chem. 2009, 74, 16, 5947-5952.

5. “Highly Efficient Synthesis of Tri- and Tetrasubstituted Conjugated Enynes from Brønsted Acid-Catalyzed Alkoxylation of 1-Cyclopropylprop-2-yn-1-ols with Alcohols”, Mothe, S. R.; Chan, P. W. H. J. Org. Chem. 2009, 74, 16, 5887-5893 (highlighted in SYNFACTS, Synfacts 2009, 11, 1230-1230).

6. “Ytterbium(III) Triflate-Catalyzed Amination of 1-Cyclopropylprop-2-yn-1-ols as an Expedient Route to Conjugated Enynes”, Rao, W.; Zhang, X.; Sze, E. M. L.; Chan, P. W. H. J. Org. Chem. 2009, 74, 4, 1740-1743.

7. “Gold- and Silver-Catalyzed Allylic Alkylation of 1,3-Dicarbonyl Compounds with Allylic Alcohols”, Kothandaraman, P.; Rao, W.; Zhang, X.; Chan, P. W. H. Tetrahedron 2009, 65, 9, 1833-1838 (invited paper for the Symposia-In-Print series on Catalysis using Gold Complexes).

8. “Copper Iodide-Catalyzed Aziridination of Alkenes with Sulfonamides and Sulfamate Esters”, Chang, J. W. W.; Ton, T. M. U.; Zhang, Z.; Xu, Y.; Chan, P. W. H. Tetrahedron Lett. 2009, 50, 2, 161-164.

9. “Gold- and Silver-Catalyzed Tandem Amination/Ring Expansion of Cyclopropylmethanols with Sulfonamides as an Expedient Route to Pyrrolidines”, Rao, W.; Chan, P. W. H. Chem. Eur. J. 2008, 14, 33, 10486-10495.

10. “Iodine-Catalyzed Allylic Alkylation of Thiols with Allylic Alcohols”, Zhang, X.; Rao, W.; Chan, P. W. H. Synlett 2008, Special Issue, 2204-2208 (chosen by the editor to feature in issue dedicated to Prof. Sir J. E. Baldwin’s 70^th birthday).

11. “Gold-Catalysed Allylic Alkylation of Aromatic and Heteroaromatic Compounds with Allylic Alcohols”, Rao, W.; Chan, P. W. H. Org. Biomol. Chem. 2008, 6, 13, 2426-2433.

12. “Dielectric Anisotropy of a Homochiral Rare-Earth Metal Complex”, Wang, G.-X.; Han, G.-F.; Ye, Q.; Xiong, R.-G.; Akutagawa, T.; Nakamura, T.; Chan, P. W. H.; Huang, S. D. J. Chem. Soc., Dalton Trans. 2008, 2527–2530.

13. “Iodine-Catalyzed Allylic Alkylation of Sulfonamides and Carbamates with Allylic Alcohols at Room Temperature”, Wu, W.; Rao, W.; Er, Y. Q.; Loh, J. K.; Poh, C. Y.; Chan, P. W. H. Tetrahedron Lett. 2008, 49, 16, 2620-2624; Tetrahedron Lett. 2008, 49, 33, 4981 (cited in the “Highlights from the Literature” section of the journal Organic Process Research and Development, Org. Process Res. Dev. 2008, 12, 358).

14. “Copper-Catalyzed Ullmann Coupling under Ligand and Additive Free Conditions. Part 2: S-Arylation of Thiols with Aryl Iodides”, Buranaprasertsuk, P.; Chang, J. W. W.; Chavasiri, W.; Chan, P. W. H. Tetrahedron Lett. 2008, 49, 12, 2023-2025.

15. “Copper-Catalyzed Ullmann Coupling under Ligand and Additive Free Conditions. Part 1: O-Arylation of Phenols with Aryl Halides”, Chang, J. W. W.; Chee, S.; Mak, S.; Buranaprasertsuk, P.; Chavasiri, W.; Chan, P. W. H. Tetrahedron Lett. 2008, 49, 12, 2018-2022.

16. “Highly Efficient Ruthenium(II) Porphyrin-Catalyzed Amidation of Aldehydes”, Chang, J. W. W.; Chan, P. W. H. Angew. Chem., Int. Ed. 2008, 47, 6, 1138-1140.

17. “Huge Deuterated Effect on Permittivity in a Metal-Organic Framework”, Zhao, H.; Ye, Q.; Qu, Z.-R.; Fu, D.-W.; Xiong, R.-G.; Huang, S. D.; Chan, P. W. H. Chem. Eur. J. 2008, 14, 4, 1164-1168.

18. “Multiferroic Homochiral Metal-Organic Framework”, Ye, Q.; Fu, D.-W.; Tian, H.; Xiong, R.-G.; Chan, P. W. H.; Huang, S. D. Inorg. Chem. 2008, 47, 3, 772-774.

19. “Iodine-Catalyzed Allylation of 1,3-Dicarbonyl Compounds with Allylic Alcohols at Room Temperature”, Rao, W.; Tay, A. H. L.; Goh, P. J.; Choy, J. M. L.; Ke, J. K.; Chan, P. W. H. Tetrahedron Lett. 2008, 49, 1, 122-126; Tetrahedron Lett. 2008, 49, 34, 5115.

20. “Deuteration Effect of Ferroelectricity and Permittivity on Homochiral Zinc Coordination Compound”, Ye, Q.; Song, Y.-M.; Fu, D.-W.; Wang, G.-X.; Xiong, R.-G.; Chan, P. W. H.; Huang, S. D. Cryst. Growth Des. 2007, 7, 9, 1568-1570.

21. “Huge Anisotropic and Deuterated Effect on Permittivity in an Olefin-Copper(I) Complex”, Ye, Q.; Song, Y.-M.; Zhao, H.; Qu, Z.-R.; Fu, D.-W.; Pang, J.; Xiong, R.-G.; Akutagawa, T.; Chan, P. W. H.; Nakamura, T. Angew. Chem., Int. Ed. 2007, 46, 36, 6852-6856.

22. “Stereoselective Synthesis of Trans-a-ketohydrazones from Silyl Enol Ethers Mediated by Iodobenzene Diacetate”, Rao, W.; Chan, P. W. H. Tetrahedron Lett. 2007, 48, 22, 3789-3792.

23. “Dielectric Anisotropy of a Homochiral Trinuclear Nickel(II) Complex”, Fu, D.-W.; Song, Y.-M.; Wang, G.-X.; Ye, Q.; Xiong, R.-G.; Akutagawa, T.; Nakamura, T.; Chan, P. W. H.; Huang, S. D. J. Am. Chem. Soc. 2007, 129, 17, 5346-5347.

24. “Practical Copper-Catalyzed N-Arylation of Nitrogen Heterocycles with Aryl Halides under Ligand and Additive Free Conditions”, Chang, J. W. W.; Xu, X.; Chan, P. W. H. Tetrahedron Lett. 2007, 48, 2, 245-248.

25. “Homochiral 1D Zinc-Quitenine Coordination Polymer with a High Dielectric Constant”, Tang, Y.-Z.; Huang, X.-F.; Song, Y.-M.; Chan, P. W. H.; Xiong, R.-G. Inorg. Chem. 2006, 45, 13, 4868-4870.

26. “Ferroelectric Metal-Organic Framework with a High Dielectric Constant”, Ye, Q.; Chen, K.; Wang, G.-X.; Fu, D.-W.; Chan, P. W. H.; Zhu, J.-S.; Huang, S. D.; Xiong, R.-G. J. Am. Chem. Soc. 2006, 128, 20, 6554-6555.

Pre-NTU Publications

27. “Enantioselective Intramolecular Cyclopropanation of Cis-Alkenes by Chiral Ruthenium(II) Schiff-Base Catalysts and Crystal Structures of (Schiff-Base)ruthenium Complexes Containing Carbene, PPh₃ and CO Ligands”, Li, G.-Y.; Zhang, J.; Chan, P. W. H.; Xu, Z.-J.; Zhu, N.-Y.; Che, C.-M. Organometallics 2006, 26, 7, 1676-1688.

28. “Gold(III) Porphyrin-Catalyzed Cycloisomerization of Allenones”, Zhou, C.-Y.; Chan, P. W. H.; Che, C.-M. Org. Lett. 2006, 8, 2, 325-328.

29. “Aryl Iodide-Mediated Aziridination of Alkenes”, Li, J.; Chan, P. W. H.; Che, C.-M. Org. Lett. 2005, 7, 26, 5801-5804.

30. “Enantioselective Intramolecular Amidation of Sulfamate Esters Catalyzed by Chiral Manganese(III) Schiff-Base Complexes”, Zhang, J.; Chan, P. W. H.; Che, C.-M. Tetrahedron Lett. 2005, 46, 32, 5403-5408.

31. “Syntheses, Crystal Structures, and Luminescent Properties of Three Novel Zinc Coordination Polymers Containing Tetrazolyl Ligands”, Wang, X.-S.; Tang, Y.-Z.; Qu, Z.-R.; Che, C.-M.; Chan, P. W. H.; Xiong, R.-G. Inorg. Chem. 2005, 44, 15, 5278-5285.

32. “Chiral Osmium Complexes with Sterically Bulky Schiff-base Ligands. Crystal Structures of Os(IV) Derivatives and the Reactivity and Catalytic Cyclopropanation of Alkenes with EDA”, Zhang, J.; Liang, J.-L.; Sun, X.-R.; Zhou, H.-B.; Zhu, N.-Y.; Zhou, Z.-Y.; Chan, P. W. H.; Che, C.-M. Inorg. Chem. 2005, 44, 11, 3942-3954.

33. “Functionalized Arylacetylene Oligomers for Organic Thin Film Transistors (OTFTs)”, Roy, V. A. L.; Zhi, Y.-G.; Xu, Z.-X.; Yu, S.-C.; Chan, P. W. H.; Che, C.-M. Adv. Mater. 2005, 17, 10, 1258-1261.

34. “Ruthenium Porphyrin Catalyzed Tandem Sulfonium/Ammonium Ylide Formation and [2,3]-Sigmatropic Rearrangement. A Concise Synthesis of (±)-Platynecine”, Zhou, C.-Y.; Yu, W.-Y.; Chan, P. W. H.; Che, C.-M. J. Org. Chem. 2004, 69, 21, 7072-7082.

35. “Ruthenium(II) Porphyrin-Catalyzed Amidation of Aromatic Heterocycles”, He, L.; Chan, P. W. H.; Tsui, W.-M.; Yu, W.-Y.; Che, C.-M. Org. Lett. 2004, 6, 14, 2405-2408.

36. “Aziridination of Alkenes with N-Substituted Hydrazines Mediated by Iodobenzene Diacetate”, Li, J.; Liang, J.-L.; Chan, P. W. H.; Che, C.-M. Tetrahedron Lett. 2004, 45, 12, 2685-2688.

37. “Ruthenium(II) Porphyrin Catalyzed Imine Aziridination and Crystal Structures of Meso-tetrakis(pentafluorophenyl) porphyrinatoruthenium(II) Complexes Containing PhN=CH(p-ClPh), CPh₂ and Pyridine Ligands”, Li, Y.; Chan, P. W. H.; Zhu, N.-Y.; Che, C.-M.; Kwong, H.-L. Organometallics 2004, 23, 1, 54-66.

38. “Ruthenium(II) Porphyrin Catalyzed Cyclopropanation of Alkenes with Tosylhydrazones”, Zhang, J.-L.; Chan, P. W. H.; Che, C.-M. Tetrahedron Lett. 2003, 44, 48, 8733-8737.

39. “Diastereoselective Atom Transfer Radical Cyclization Reactions of Unsaturated a-Bromo-Oxazoladinone Imides Catalyzed by Lewis Acids”, Yang, D.; Zheng, B.-F.; Gu, S.; Chan, P. W. H.; Zhu, N.-Y. Tetrahedron: Asymmetry 2003, 14, 19, 2927-2937.

40. “Chiral Rhodium(II,II) Dimers Catalyzed Enantioselective Intramolecular Aziridination of Sulfonamides and Carbamates”, Liang, J.-L.; Yuan, S.-X.; Chan, P. W. H.; Che, C.-M. Tetrahedron Lett. 2003, 44, 31, 5917-5920.

41. “Study of Substrate Dependence on the Diastereoselectivity of the Ruthenium(II) Porphyrin Catalyzed Tandem Formation and 1,3-Dipolar Cycloaddition Reactions of Carbonyl Ylides” Zhou, C.-Y.; Chan, P. W. H.; Yu, W.-Y.; Che, C.-M. Synthesis 2003, 9, 1403-1412.

42. “Rhodium(II,II) Dimer as an Efficient Catalyst for the Aziridination of Sulfonamides and Amidation of Steroids”, Liang, J.-L.; Yuan, S.-X.; Chan, P. W. H.; Che, C.-M. Org. Lett. 2002, 4, 25, 4507-4510.

43. “Syntheses of the AB and EFGH Ring Segments of Gambierol”, Kadota, I.; Kadowaki, C.; Park, C.-H.; Takamura, H.; Sato, K.; Chan, P. W. H.; Thorand, S.; Yamamoto, Y. Tetrahedron 2002, 58, 10, 1799-1816.

44. “Pyrrolidinone Analogues Derived from (S)-Pyroglutamic Acid. Part 4. a,b-Diaminopyrrolidinones”, Chan, P. W. H.; Cottrell, I. F.; Moloney, M. G. J. Chem. Soc., Perkin Trans. 1 2001, 22, 3007-3012.

45. “Pyrrolidinone Analogues Derived from (S)-Pyroglutamic Acid. Part 3. b-Aminopyrrolidinones”, Chan, P. W. H.; Cottrell, I. F.; Moloney, M. G. J. Chem. Soc., Perkin Trans. 1 2001, 22, 2997-3006.

46. “Lewis Acid Catalyzed Reaction of Aromatic Vinyl Halides with Aromatic Aldehydes: A Novel Aldol-type Condensation Mimic”, Chan, P. W. H.; Kamijo, S.; Yamamoto, Y. Synlett 2001, Special Issue, 910-913.

47. “A Novel Convergent Approach to trans-Fused Polyether Frameworks Based on the Reaction of Vinylstannanes and Triflates and its Application to a Synthetic Study of the EFGH Ring System of Gambierol”, Kadowaki, C.; Chan, P. W. H.; Kadota, I.; Yamamoto, Y. Tetrahedron Lett. 2000, 41, 30, 5769-5772.

48. “Azosugars: A Conformationally Restricted Vicinal 3,4-Diamine Derived from (S)-(-)-Pyroglutamic Acid”, Chan, P. W. H.; Cottrell, I. F.; Moloney, M. G. Tetrahedron: Asymmetry 1999, 10, 20, 3887-3891.

49. “Conjugate Addition of Nitrogen Nucleophiles to an a,b-Unsaturated Pyrrolidinone”, Chan, P. W. H.; Cottrell, I. F.; Moloney, M. G. Tetrahedron Lett. 1997, 38, 33, 5891-5894.

Review and Conference Publications and Highlighted Works

NTU Publications

1. “Copper Iodide-Catalyzed Amidation of Aldehydes”, Chang, J. W. W.; Chan, P. W. H. Abstracts of Papers of the American Chemical Society 2009, 238.

2. “Gold-Catalyzed Strategies for Swapping C-OH Bonds for C-C and C-N Bonds”, Chan, P. W. H. Gold2009 – The 5^th International Conference on Gold Science, Technology and its Applications 2009, 137.

3. “Ytterbium(III) Triflate-Catalyzed Tandem Friedel-Crafts Alkylation/Hydroarylation of Propargylic Alcohols with Phenols as an Expendient Route to Indenols”, Zhang, X.; Chan, P. W. H. Frontiers in Chemistry Symposium 2009, C89.

4. “Highly Efficient Synthesis of Tri- and Tetrasubstituted Conjugated Enynes from Brønsted Acid-Catalyzed Alkoxylation of 1-Cyclopropylprop-2-yn-1-ols with Alcohols”, Mothe, S. R.; Chan, P. W. H. Frontiers in Chemistry Symposium 2009, C59.

5. “Lewis and Brønsted Acid-Catalyzed Reactions of Alcohol Pro-Electrophiles”, Chan, P. W. H. Frontiers in Chemistry Symposium 2009, C20.

6. “Lewis and Brønsted Acid-Catalyzed Reactions of Alcohol Pro-Electrophiles”, Chan, P. W. H. NanoCat Symposium 2009, 20.

7. “Lewis and Brønsted Acid-Catalyzed Reactions of Alcohol Pro-Electrophiles”, Chan, P. W. H. 2^nd NTU – Waseda University Joint Symposium in Chemistry 2009, 10.

8. “Highly Efficient Ruthenium(II) Porphyrin-Catalyzed Amidation of Aldehydes”, Chang, J. W. W.; Chan, P. W. H. 11^th Belgian Organic Chemistry Symposium 2008, P62, 88.

9. “Iodine-Catalyzed Allylic Alkylation of Sulfonamides and Carbamates with Allylic Alcohols at Room Temperature”, Wu, W.; Rao, W.; Er, Y. Q.; Loh, J. K.; Poh, C. Y.; Chan, P. W. H. Tetrahedron Lett. 2008, 49, 16, 2620-2624; highlighted in “Highlights from the Literature” section in Org. Process Res. Dev. 2008, 12, 3, 358-368.

10. “Exploring the Alcohol Approach for the Development of New Carbon-Carbon and Carbon-Nitrogen Bond Formation Strategies”, Chan, P. W. H. 2^nd UK-Singapore Symposium – Contemporary Organic Synthesis, Methods and Techniques, 2008, 5.

11. “Iodine-Catalyzed Amination of Allylic Alcohols”, Wu, W.; Chan, P. W. H. International Symposium on Catalysis and Fine Chemicals 2007, 2007, A 357.

12. “AuCl₃-Catalyzed Arene and Heteroarene Allylation and Propargylation with Allylic and Propargylic Alcohols”, Rao, W.; Chan, P. W. H. International Symposium on Catalysis and Fine Chemicals 2007, 2007, A268.

13. “Exploring the Alcohol Approach for the Development of New Carbon-Carbon and Carbon-Nitrogen Bond Formation Strategies”, Chan, P. W. H. International Symposium on Catalysis and Fine Chemicals 2007, 2007, A 259.

14. “Copper-Catalyzed N-, O- and S-Arylation of Azoles, Phenols and Thiols with Aryl Halides”, Chang, J. W. W.; Chan, P. W. H. International Symposium on Catalysis and Fine Chemicals 2007, 2007, A 188.

15. “Copper-Catalyzed N- and O-Arylation of Azoles and Phenols with Aryl Halides”, Chang, J. W. W.; Chan, P. W. H. Chemistry for Innovation, PERCH-CIC Congress V 2007, OC-P41, 237.

16. “Stereoselective Synthesis of Trans-a-Ketohydrazones From Silyl Enol Ethers Mediated by Iodobenzene Diacetate”, Rao, W.; Chan, P. W. H. Chemistry for Innovation, PERCH-CIC Congress V, 2007, OC-P33, 229.

17. “Iodobenzene Diacetate-Mediated Synthesis of Trans-a-Ketohydrazones and a-Ketohydrazines from Silyl Enol Ethers. Effect of Gold(I) Chloride on Chemoselectivity”, Chan, P. W. H.; Rao, W. Fundamentals and Applications of Organic Chemistry, A*STAR-Noyori Forum Joint Symposium, 2007, 66.

18. “Carbon-Nitrogen Bond Formation Strategies by Design – Exploring the Transition Metal-Mediated Approach”, Chan, P. W. H. First International Conference of Cutting-Edge Organic Chemistry, 2006, L21, 29.

19. “Ferroelectric Metal-Organic Framework with a High Dielectric Constant”, Ye, Q.; Chen, K.; Wang, G.-X.; Fu, D.-W.; Chan, P. W. H.; Zhu, J.-S.; Huang, S. D.; Xiong, R.-G. J. Am. Chem. Soc. 2006, 128, 20, 6554-6555; highlighted in “Editors’ Choice” section in Science 2006, 312, 974.

Pre-NTU Publications

20. “Ruthenium(II) Porphyrin Catalyzed Imine Aziridination and Crystal Structures of Meso-tetrakis(pentafluorophenyl) porphyrinatoruthenium(II) Complexes Containing PhN=CH(p-ClPh), CPh₂ and Pyridine Ligands”, Li, Y.; Chan, P. W. H.; Zhu, N.-Y.; Che, C.-M. International Symposium on Catalysis and Fine Chemicals 2004, 2004, P-101.

21. “Ruthenium Porphyrin Catalyzed Tandem Sulfonium/Ammonium Ylide Formation and [2,3]-Sigmatropic Rearrangement. A Concise Synthesis of (±)-Platynecine”, Zhou, C.-Y.; Yu, W.-Y.; Chan, P. W. H.; Che, C.-M. International Symposium on Catalysis and Fine Chemicals 2004, 2004, P-76.

22. “Chiral Dirhodium(II,II) Complexes Catalyzed Intramolecular Amidation of Sulfamate Esters and Carbamates. Catalytic and Enantioselective Studies”, Zhang, J.; Chan, P. W. H.; Che, C.-M. International Symposium on Catalysis and Fine Chemicals 2004, 2004, P-73.

23. “Towards the Total Synthesis of the Ustiloxins and Phomopsins”, Chan, P. W. H.; Cohen, S. B.; Hutton, C. A. Conference Programme and Abstracts, IUPAC 14^th International Conference on Organic Synthesis, 2002, 59.

24. “Synthetic Studies Towards the Total Synthesis of the Ustiloxins and Phomopsins”, Chan, P. W. H.; Hutton, C. A.; Turner, J. J. Abstracts of Papers of the Royal Australian Chemical Institute, NSW Organic Group 2001, 4.

25. “The First Novel Direct Oxygen Atom Transfer from Hypervalent Oxido-l³-iodanes to a,b-Unsaturated Carbonyl Compounds to give a,b-Epoxy Carbonyl Compounds”, Chan, P. W. H.; Yamamoto, Y. Chemtracts-Org. Chem. 2001, 14, 2, 84-87.

26. “Development of a New Method for Construction of Tetrahydropyran Rings by the Reaction of Vinyllithiums and Triflates”, Chan, P. W. H.; Kadota, I.; Kadowaki, C.; Park, C. H.; Yamamoto, Y. Abstracts of Papers of the Japanese Chemical Society 2000, 78, 2E609, 880.

27. “The Direct Catalytic Asymmetric Aldol Reaction using Rare Earth-Based Heterobi- and Heteropolymetallic BINOL Complexes”, Chan, P. W. H.; Yamamoto, Y. Chemtracts-Org. Chem. 2000, 13, 1, 14-19.

28. “Conjugate Addition of Nitrogen Nucleophiles to an Unsaturated Pyrrolidinone”, Chan, P. W. H.; Cottrell, I. F.; Moloney, M. G. Abstracts of Papers of the American Chemical Society 1998, 215, No.Pt.2, 55.

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