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Department of Chemistry

Prof. Philip Chan

 
Prof. Philip Wai Hong Chan

Monash-Warwick Alliance Chair Professor of Sustainable Chemistry

B.Sc. (Bristol), D.Phil. (Oxford)

Contact Details

Room: 222, Green Chemical Futures Building
Phone: +61 3 9905 1337
Fax: +61 3 9905 4597
Email: phil.chan@monash.edu
P.W.H.Chan@warwick.ac.uk

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Research Summary
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The interests of the group focus on the development of operationally straightforward and practical synthetic strategies for C-C and C-X (X = N, O, S) bond formation that follows the principles of environmental sustainability and which is of broad utility to synthetic organic chemistry. We are drawn to the design of stereoselective multiple bond forming synthetic methods that can be achieved under mild conditions with ecologically benign catalysts and significantly minimize and/or eliminate the consumption of a variety of material and energy resources as well as the production of chemical waste. Three thematic approaches of the group are: (1) Lewis and Brønsted acid-catalyzed C-OH bond activation; (2) gold-catalyzed cycloisomerization of alkynes; and (3) transition metal- and Brønsted acid-mediated chemistry of iminoiodanes. The application of these novel catalytic methodologies to the construction of bioactive natural products and as practical synthetic tools for the assembly of complex molecules of current biological and materials interest is also pursued.

Publications
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1. “Ligand-Controlled Product Chemoselectivity in Gold-Catalyzed Double Cycloisomerization of 1,11-Dien-3,9-Diyne Benzoates”, Rao, W.; Susanti, D.; Ayers, B. J.; Chan, P. W. H. J. Am. Chem. Soc. 2015, 137, 19, 6350-6355.

2. Silver-Catalyzed Tandem Hydroamination/Hydroarylation of 1-(2-Allylamino)phenyl-4-hydroxy-but-2-yn-1-ones to 1'-Allylspiro[indene-1,2'-indolin]-3'-ones”, Mothe, S. R.; Novianti, M. L.; Ayers, B. J.; Chan, P. W. H. Org. Lett. 2014, 16, 16, 4110-4113.

3. “Gold-Catalyzed Benzannulation of 5-Hydroxy-3-oxoalk-6-ynoate Esters to o-Phenolic Esters”, Teo, W. T.; Rao, W.; Ng, C. J. H.; Koh, S. W. Y.; Chan, P. W. H. Org. Lett. 2014, 16, 4, 1248-1251.

4. “Gold-Catalyzed Cycloisomerization of 1,6-Diyne Carbonates and Esters to 2,4a-Dihydro-1H-fluorenes”, Rao, W.; Koh, M. J.; Li, D.; Hirao, H.; Chan, P. W. H. J. Am. Chem. Soc. 2013, 135, 21, 7926-7932.

5. “N-Iodosuccinimide-Mediated Iodoaminocyclization of 1-(2-(Tosylamino)phenyl)prop-2-yn-1-ols to 2-(Iodomethylene)indolin-3-ones and 3-(Diiodomethyl)indolin-2-ones” Kothandaraman, P.; Koh, B. Q.; Limpanuparb, T.; Hirao, H.; Chan, P. W. H. Chem. Eur. J. 2013, 19, 6, 1978-1985.

6. “Gold-Catalyzed Cycloisomerization of 1,7-Diyne Benzoates to Indeno[1,2-c]azepines and Azabicyclo[4.2.0]octa-1(8),5-dines”, Rao, W.; Koh, M. J.; Kothandaraman, P.; Chan, P. W. H. J. Am. Chem. Soc. 2012, 134, 26, 10811-10814 (highlighted by SYNFACTS, Synfacts 2012, 9, 952).

7. "Copper(II) Triflate-Catalyzed Amination and Aziridination of 2-Alkyl Substituted 1,3-Dicarbonyl Compounds", Ton, T. M. U.; Tejo, C.; Tiong, D. L. Y.; Chan, P. W. H. J. Am. Chem. Soc. 2012, 134, 17, 7344-7350.

8. “Gold-Catalyzed Tandem 1,3-Migration/[2+2] Cycloaddition of 1,7-Enyne Benzoates to Azabicyclo[4.2.0]oct-5-enes”, Rao, W.; Susanti, D.; Chan, P. W. H. J. Am. Chem. Soc. 2011, 133, 39, 15248-15251.

9. “Gold-Catalyzed Cycloisomerization Reactions of 2-Tosylaminophenylprop-1-yn-3-ols as a Versatile Platform for Indole Synthesis”, Kothandaraman, P.; Rao, W.; Foo, S. J.; Chan, P. W. H. Angew. Chem. Int. Ed. 2010, 49, 27, 4619-4623; (chosen by the Editors of Angewandte Chemie as a Hot Paper and 6th Asian-European Symposium Poster Presentation Award).

10. “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.