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Draft:Teck-Peng Loh

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  • Comment: Please read this guide. While he merits a page, you have written an extended CV with details about all his research, neither do we want any bragging (WP:Peacock). We do not want to see his patents, you do not source the critical section on his career. Ldm1954 (talk) 14:50, 15 June 2025 (UTC)
  • Comment: This submission likely meets WP:NACADEMIC given distinguished fellow position and citations/research impact. However, there's way too many citations WP:OVERCITE and information that does not need to be part of the encyclopedic article. Please use external links for patents or list of scholarly publications. Thanks! WeWake (talk) 17:05, 11 June 2025 (UTC)
Teck-Peng Loh
Alma materTokyo Institute of Technology, Harvard University
Known forGreen Chemistry, Carbon–hydrogen bond activation
Scientific career
FieldsOrganometallic chemistry
InstitutionsNanyang Technological University
Thesis (1989-1994)
Doctoral advisorElias James Corey

Teck-Peng Loh is a professor of chemistry at Nanyang Technological University in Singapore. His research in the field of organic synthesis focuses on the development of water-compatible reactions, new synthetic methodology, and the total synthesis of architecturally complex organic molecules with notable biological activities.[1][2]

Education

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Loh received his Bachelor of Engineering in chemical sciences from the Tokyo Institute of Technology in Meguroku, Japan (1983–1987).[3] He also received his Master of Engineering in chemical sciences from the Tokyo Institute of Technology (1987–1989). During his masters, he worked on the development of the Ene reaction for steroid-side chain synthesis under supervisors Takeshi Nakai and Koichi Mikami.[3][4][5] He then went on to earn his PhD in chemistry from Harvard University working under Professor Elias James Corey (1989–1994). During his PhD, he developed a novel class of chiral catalysts for an enantioselective Diels-Alder reaction and a stereo-controlled total synthesis of epibatidine and analogs.[6]

Career

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Loh has held several prominent academic positions throughout his career.[7] Since 2005, he has served as a Professor in the Division of Chemistry and Biological Chemistry at the School of Physical and Mathematical Sciences, Nanyang Technological University (NTU), Singapore. Prior to this, he was a Professor in the Department of Chemistry at the National University of Singapore (NUS) from 2004 to 2005, having previously served as an Associate Professor from 1999 to 2004 and as a Senior Lecturer (Assistant Professor) from 1994 to 1999. He was also a Visiting Professor at Columbia Medical School at Columbia University from 2002 to 2003. Since 2002, he has concurrently held the role of Adjunct Professor at Soochow University (Suzhou) in China.

Research

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Loh and his group focus on developing new synthetic methodology that aims to advance the field of green chemistry through the use of mild conditions (room temperature, atmospheric pressure, physiological pH), minimization of waste production, and the replacement of toxic organic solvents with environmentally friendly alternatives such as water and ethanol.[8] In addition to discovering water-compatible methodologies, the group has made advancements in carbon–hydrogen bond activation chemistry. Lastly, the group has synthesized a handful of natural products inspired by biological systems.

Green chemistry

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Representative examples of green chemistry advancements produced by the Loh group include a indium-catalyzed Diels-Alder reaction at room temperature in water, a Friedel-Crafts reaction of indoles with carbonyl compounds in water, and a C–N bond formation reaction with allenic ketones in PBS buffer solution. These reactions replace organic solvents typically used in organic reactions with water to achieve biocompatible, environmentally friendly, and cost-effective conditions.

Indium-catalyzed Diels-Alder reaction in water

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An early example of green methodology published by Teck-Peng Loh is the indium trichloride (InCl3) catalyzed Diels-Alder reaction in water published in 1996.

An early example of green methodology published by the Loh group was the indium trichloride (InCl3) catalyzed Diels-Alder reaction in water published in 1996.[9] Diels-Alder adducts were produced in good to excellent yield with either cyclic or non-cyclic dienes, as well as chiral dienophiles. For the reaction of acrolein with cyclopentadiene in the presence of InCl3 (20 mol%), the Diels-Alder product was obtained in 100% yield with 90:10 endo:exo selectivity (compared to 60% yield and 74:26 endo:exo without catalyst).

Friedel-Crafts reactions of indoles with carbonyl compounds in water

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In 2022, Loh and coworkers published a Friedel-Crafts type reaction of indoles with carbonyl compounds in water to afford 3,3’-bisindolylmethanes (BIMs).

In 2022, Loh and coworkers published a Friedel-Crafts type reaction of indoles with carbonyl compounds to afford 3,3'-bisindolylmethanes (BIMs) catalyzed by a super acidic species formed by trityl tetrakis(pentrafluorophenyl)borate in water.[10] The reaction can handle a broad substrate scope, 0.08 mol% catalyst loading, and can be scaled up to 100 grams without decreasing efficiency.

C–N bond formation reaction with allenic ketones in PBS buffer solution

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In 2022, Loh and coworkers published a biocompatible amination of allenic ketones in a phosphate buffer system under catalyst-free conditions at room temperature.

Also in 2022, Loh and coworkers published a biocompatible amination of allenic ketones in a phosphate buffer system under catalyst-free conditions at room temperature.[11] A diverse range of β-keto enamines are obtained in modest to excellent yields with high regioselectivity. The reaction is also applicable to bioconjugation.

C–H functionalization

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In addition to green chemistry, the Loh group also focuses on developing carbon–hydrogen bond activation reactions to access substituted species. Representative examples include the copper-catalyzed olefinic trifluoromethylation of enamides and base-mediated C–H cyanation of sulfonamides.

Copper-catalyzed olefinic trifluoromethylation of enamides

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In 2012, Loh and coworkers published the first known olefinic C–CF3 bond formation reaction from cleavage of an olefinic C–H bond.

Motivated by the use of the trifluoromethyl group in the pharmaceutical and agrochemical industries, Loh and coworkers published the first known olefinic C–CF3 bond formation reaction from displacement of an olefinic C–H bond in 2012.[12] The reaction is catalyzed by a copper(I) (Cu(I)) complex to deliver E-selective products in high to excellent yields through a cationic reaction mechanism. Togni's reagent is activated by Cu(I) to form a cationic intermediate which then reacts with the enamide to ultimately form an ⍺-trifluoromethyl imine intermediate. The imine intermediate undergoes ⍺-proton elimination or transfer to deliver the final olefinic trifluoromethylated product and regenerate the Cu(I) catalyst.

Synthesis of ⍺-amino nitriles from sulfonamides via base-mediated C–H cyanation

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In 2021, Loh and coworkers developed a metal-free C–H cyanation of sulfonamides to afford ⍺-amino nitriles.

In 2021, Loh and coworkers developed a metal-free C–H cyanation of sulfonamides to afford a broad range of ⍺-amino nitriles,[13] substrates used in syntheses of alkaloids, amino acids, heterocycles, and pharmaceuticals. The protocol proceeded with both primary amides and secondary amides via formation of an imine intermediate through base-promoted elimination of hydrogen fluoride (HF).

Natural product total syntheses

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Loh and his research group have synthesized several natural products:

Awards and recognition

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Professor Loh has received Best Researcher Awards from both the National University of Singapore (NUS) and Nanyang Technological University (NTU Singapore), the GSK-SNIC Award in Organic Chemistry (Singapore), the Thousand Talent Award (China), and the Yoshida Prize (Japan).[20] In 2018, he received the Singaporean President's Science Award. He is an elected Fellow of both the Malaysia Academy of Sciences and the Singapore Academy of Sciences. Professor Loh has served on the advisory boards of Chemical Communications, Synlett, Synthesis, Heterocycles, Chemical Record, and the Asian Journal of Organic Chemistry, and is currently an associate editor of the Journal of Organic Chemistry.

Patents

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The following patents were sourced from World Intellectual Property Organization (WIPO) Patentscope.[21]

  • Method of synthesizing alpha-amino acid derivatives, U.S. Patent No. 20200361863, published November 19, 2020.[22]
  • Allenamide as an orthogonal handle for selective modification of cysteine in peptides and proteins, U.S. Patent No. 20170029373, granted May 21, 2019.[23]
  • Tricyclic chiral compounds and their use in asymmetric catalysis, U.S. Patent No. 20160207932, granted May 15, 2018.[24]
  • 3-Piperidone compounds and their use as a neurokinin-1 (NK1) receptor antagonists, U.S. Patent No. 20160031817, granted November 29, 2016.[25]
  • Small molecule catalysts for 5-hydroxymethylfurrfural production from saccharides, U.S. Patent No. 20150166499, granted March 8, 2016.[26]
  • Method for the synthesis of an amino acetal, U.S. Patent No. 20130165682, granted July 14, 2015.[27]
  • Tricyclic chiral compounds and their use in asymmetric catalysis, U.S. Patent No. 20110269972, granted December 8, 2015.[28]
  • Octahydro biquinoline compound, U.S. Patent No. 20120088916, granted April 8, 2014.[29]
  • Cyclisation process of forming a multiple ring compound, U.S. Patent No. 20130046090, granted January 14, 2014.[30]
  • Cyclisation process of forming a multiple ring compound, U.S. Patent No. 20100228058, granted July 24, 2012.[31]

References

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  1. ^ "Prof Loh Teck Peng". Nanyang Technological University. Retrieved 9 June 2025.
  2. ^ "Professor LOH Teck Peng". personal.ntu.edu.sg.
  3. ^ a b "Professor LOH Teck Peng". personal.ntu.edu.sg.
  4. ^ Mikami, Kōichi; Loh, Teck-Peng; Nakai, Takeshi (1 January 1988). "Ene approach for concurrent control over the chiral centres at C-20 and C-22 of steroid side chains: a highly stereocontrolled synthesis of (20S,22R)-(erythro-)22-hydroxy-23,24-acetylenic steroid side chains". Journal of the Chemical Society, Chemical Communications (21): 1430–1431. doi:10.1039/C39880001430.
  5. ^ Mikami, Kōichi; Loh, Teck-Peng; Nakai, Takeshi (1 January 1988). "Diastereocontrol via lewis acid-promoted ene reaction with glyoxylates and its application to stereocontrolled synthesis of a 22R-hydroxy-23-carboxylate steroid side chain". Tetrahedron Letters. 29 (48): 6305–6308. doi:10.1016/S0040-4039(00)82332-1.
  6. ^ Loh, Teck Peng (10 January 1994). "Part I. Design of catalysts for enantioselective Diels-Alder reaction. Part II. Stereocontrolled total synthesis of (+)- and (-)-epibatidine and analogs". ProQuest. Retrieved 9 June 2025.
  7. ^ "Prof Loh Teck Peng". Nanyang Technological University. Retrieved 9 June 2025.
  8. ^ Lu, Ming-Zhu; Loh, Teck-Peng (2 January 2024). "Development and Applications of Water-Compatible Reactions: A Journey to Be Continued". Accounts of Chemical Research. 57 (1): 70–92. doi:10.1021/acs.accounts.3c00555. PMID 38112292.
  9. ^ Loh, Teck-Peng; Pei, Jian; Lin, Mei (1996). "Indium trichloride (InCl 3 ) catalysed Diels–Alder reaction in water". Chem. Commun. (20): 2315–2316. doi:10.1039/CC9960002315.
  10. ^ Zhang, Zhenguo; Ji, Liang; Liu, Xiaoxiao; Li, Zhihong; Lv, Yongheng; Jia, Zhenhua; Loh, Teck-Peng (2022). "Metal-free synthesis of 3,3′-bisindolylmethanes in water using Ph 3 C + [B(C 6 F 5 ) 4 ] − as the pre-catalyst". Organic Chemistry Frontiers. 9 (19): 5154–5159. doi:10.1039/d2qo01081j.
  11. ^ Goh, Jeffrey; Ong, Seng Kheong; Tan, Yan Sheng; Loh, Teck-Peng (2022). "Catalyst-free C–N bond formation under biocompatible reaction conditions". Green Chemistry. 24 (8): 3321–3325. doi:10.1039/d2gc00027j.
  12. ^ Feng, Chao; Loh, Teck-Peng (2012). "Copper-catalyzed olefinic trifluoromethylation of enamides at room temperature". Chemical Science. 3 (12): 3458. doi:10.1039/c2sc21164e.
  13. ^ Shi, Shasha; Yang, Xianyu; Tang, Man; Hu, Jiefeng; Loh, Teck-Peng (21 May 2021). "Direct Synthesis of α-Amino Nitriles from Sulfonamides via Base-Mediated C–H Cyanation". Organic Letters. 23 (10): 4018–4022. doi:10.1021/acs.orglett.1c01232. PMID 33970649.
  14. ^ Wang, Shun-Yi; Song, Ping; Chin, Yen-Jin; Loh, Teck-Peng (February 2011). "A General Strategy for the Introduction of Stereogenic Centers Bearing a Methyl Group: Total Synthesis of Sex Pheromones". Chemistry – an Asian Journal. 6 (2): 385–388. doi:10.1002/asia.201000663. PMID 21254416.
  15. ^ Wang, Shun-Yi; Song, Ping; Chan, Li-Yan; Loh, Teck-Peng (19 November 2010). "Total Synthesis of Phytophthora Mating Hormone α1". Organic Letters. 12 (22): 5166–5169. doi:10.1021/ol102177j. PMID 20973505.
  16. ^ Zhou, Hai; Loh, Teck-Peng (29 July 2009). "One-pot total syntheses of natural products containing a THP-ring backbone: (±)-centrolobine and (±)-civet cat secretion". Tetrahedron Letters. 50 (30): 4368–4371. doi:10.1016/j.tetlet.2009.05.053.
  17. ^ Zhao, Yu-Jun; Loh, Teck-Peng (5 June 2008). "Asymmetric Total Synthesis of Antiochic Acid". Organic Letters. 10 (11): 2143–2145. doi:10.1021/ol800499p. PMID 18439020.
  18. ^ Lee, Kiew-Ching; Loh, Teck-Peng (2006). "Total synthesis of antillatoxin". Chemical Communications (40): 4209–4211. doi:10.1039/b608193m. PMID 17031434.
  19. ^ Loh, Teck Peng (10 January 1994). "Part I. Design of catalysts for enantioselective Diels-Alder reaction. Part II. Stereocontrolled total synthesis of (+)- and (-)-epibatidine and analogs". ProQuest. Retrieved 9 June 2025.
  20. ^ "President's Science Award (PSA)". www.psta.gov.sg.
  21. ^ "WIPO - Search International and National Patent Collections". patentscope.wipo.int.
  22. ^ "WIPO - Search International and National Patent Collections". patentscope.wipo.int.
  23. ^ "WIPO - Search International and National Patent Collections". patentscope.wipo.int.
  24. ^ "WIPO - Search International and National Patent Collections". patentscope.wipo.int.
  25. ^ "WIPO - Search International and National Patent Collections". patentscope.wipo.int.
  26. ^ "WIPO - Search International and National Patent Collections". patentscope.wipo.int.
  27. ^ "WIPO - Search International and National Patent Collections". patentscope.wipo.int.
  28. ^ "WIPO - Search International and National Patent Collections". patentscope.wipo.int.
  29. ^ "WIPO - Search International and National Patent Collections". patentscope.wipo.int.
  30. ^ "WIPO - Search International and National Patent Collections". patentscope.wipo.int.
  31. ^ "WIPO - Search International and National Patent Collections". patentscope.wipo.int.
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