Chao-Jun Li

Summary

Chao-Jun "C.-J." Li, a Canadian chemist, is E. B. Eddy Professor of Chemistry and Canada Research Chair in Green Chemistry at McGill University, Montréal. He is known for his pioneering works in Green Solvent (organic reactions in water) and Green Syntheses (water/functional group-tolerating organometallics, C-H activation, and photochemistry).

Chao-Jun Li
Alma materZhengzhou University (BSc)

Chinese Academy of Science (MSc)
McGill University (PhD)

Stanford University (postdoctoral work)
Awards1998 US NSF CAREER Award

2001 US Presidential Green Chemistry Challenge Award (Academic)
2007 Fellow of the Royal Society of Chemistry (UK)
2012 Fellow of the Royal Society of Canada (Academy of Sciences)
2012 Fellow of the American Association for the Advancement of Science
2012 Fellow of the Chemical Institute of Canada
2015 Fellow of the American Chemical Society
2016 Fellow of The World Academy of Sciences (TWAS)
2020 Fellow of the Chinese Chemical Society
2020 Fellow of The European Academy of Sciences
2021 Humboldt Prize

2022 CIC Medal
Scientific career
FieldsGreen chemistry, organic chemistry
InstitutionsMcGill University (2003-present) Tulane University (1994–2003)
Academic advisorsTak-Hang Chan

David Harpp

Barry Trost
Websitehttp://www.cjlimcgill.ca/

Education edit

C.-J. Li was born in 1963, and obtained his BSc from Zhengzhou University (1979–1983), and completed his MSc. in organic synthesis at the Chinese Academy of Sciences (1985–1988) with Prof. T.H. Chan.[1] He then moved to McGill University (Montréal, Québec) to do his PhD (1989–1992) with Prof. T.H. Chan again (and discovered the indium-mediated allylation reaction in water) along with Prof. David Harpp (working on organosulfur/selenium/tellurium chemistry), and went on a NSERC-funded postdoc with Prof. Barry Trost at Stanford University in the United States (1992–1994) (and discovered the so-called phosphine-catalyzed γ-Addition Reaction).

Career and research edit

C.-J. Li started as an assistant professor at Tulane University in 1994, and attained the title of Professor of Chemistry in 2000. He then moved in 2003 to McGill University, where he obtained a Canada Research Chair (Tier I) in Green Chemistry.[2] He has also been the director of NSERC CREATE for Green Chemistry (2012–2018), the director of CFI Infrastructure for Green Chemistry and Green Chemicals (2008–2018) and has been the co-director of the FQRNT Center for Green Chemistry and Catalysis since 2009. He was the founding Co-Chair of the Canadian Green Chemistry and Engineering Network.

C.-J. Li's research encompasses various aspects of green chemistry applied to organic chemistry: organometallics, catalysis (thermal and light-based). Most notably, he is known for introducing water as a Green Solvent[3] for various chemical reactions (C-H activation/Functionalization,[4] Grignard type-reactions in water.[5][6] Li originated the concepts of Aldehyde-Alkyne-Amine Coupling (A3 coupling reaction) and the cross dehydrogenative coupling (CDC Reaction, or C-H/C-H coupling, or oxidative C-H cross coupling). His work on GaN nanowires and nanoparticals as photocatalysts for the conversion of methane into benzene was covered by Phys.org in 2015, leaving prospects for hydrogen storage.[7] Subsequently, his team showed that they were also able to convert methanol into ethanol,[8] ethylene and cyclohexane. He also made breakthroughs in using hydrazones as organometallic surrogates in nucleophilic addition and cross-coupling,[9] the direct amination of phenol derivatives.[10] and the earliest report on fluorescence enhancement due to self-assembling (SAFE) in solution.[11]

Selected publications edit

Reactions in water:

A3 coupling reaction[16][17]

Cross dehydrogenative coupling(CDC)[18]

GaN Photocatalysts

  • Photoinduced conversion of methane into benzene over GaN nanowires[19]
  • Direct catalytic methanol-to-ethanol photoconversion via methyl carbene[20]
  • Direct catalytic conversion of methane into cyclohexane (Methane Liquefaction)[21]
  • Direct catalytic conversion of methane into methanol or formic acid[22]

Hydrazones as organo-metallic equivalent (HOME Chemistry):

  • Carbonyls as alkyl carbanion equivalents for 1,2-nucleophilic additions, conjugate additions, and cross-couplings [23][24][25]

References edit

  1. ^ "New Associate Editor – The Americas". Green Chemistry. 7 (2): 58. 2005. doi:10.1039/B500233H.
  2. ^ Government of Canada, Industry Canada (2012-11-29). "Canada Research Chairs". www.chairs-chaires.gc.ca. Retrieved 2020-04-18.
  3. ^ Li, Chao-Jun (1993-09-01). "Organic Reactions in Aqueous Media-with a Focus on Carbon-Carbon Bond Formations". Chemical Reviews. 93 (6): 2023–2035. doi:10.1021/cr00022a004.
  4. ^ Wei, Chunmei; Li, Chao-Jun (2002-01-25). "Grignard type reaction via C–H bond activation in water". Green Chemistry. 4 (45): 39–41. doi:10.1039/B110102C.
  5. ^ Li, Chao-Jun (1996-04-25). "Aqueous Barbier-Grignard type reactions: scope, mechanism, and synthetic applications". Tetrahedron. 52 (16): 5643–5668. doi:10.1016/0040-4020(95)01056-4.
  6. ^ "A breakthrough for organic reactions in water". ScienceDaily. Retrieved 2020-04-17.
  7. ^ "Simple hydrogen storage solution is powered by solar energy". phys.org. Retrieved 2020-04-17.
  8. ^ Service, Robert F. (19 February 2019). "Ultraviolet light could provide a powerful new source of green fuel". Science. Archived from the original on 2019-02-19.
  9. ^ "Carbanion analogs derived from naturally-occurring aldehydes". phys.org. Retrieved 2020-04-17.
  10. ^ "Palladium-catalyzed Deoxygenative Amination Of Phenols". Science Trends. 2017-12-04. Retrieved 2020-04-17.
  11. ^ Xia, Wen-Sheng; Schmehl, Russell H.; Li, Chao-Jun (1999-05-27). "A highly selective fluorescent chemosensor for K+ from a bis-15-crown-5 derivative". Journal of the American Chemical Society. 121 (23): 5599–5600. doi:10.1021/ja984462c.
  12. ^ Li, Chao-Jun; Chan, Tak-Hang (1991-11-25). "Organometallic Reactions in Aqueous Media with Indium". Tetrahedron Letters. 32 (48): 7107–7120. doi:10.1016/0040-4039(91)85028-4.
  13. ^ Keh, Charlene C. K.; Wei, Chunmei; Li, Chao-Jun (March 2003). "The Barbier−Grignard-Type Carbonyl Alkylation Using Unactivated Alkyl Halides in Water". Journal of the American Chemical Society. 125 (14): 4062–4063. doi:10.1021/ja029649p. PMID 12670223.
  14. ^ Zhou, Feng; Li, Chao-Jun (September 2014). "The Barbier–Grignard-type arylation of aldehydes using unactivated aryl iodides in water". Nature Communications. 5 (1): 4254. Bibcode:2014NatCo...5.4254Z. doi:10.1038/ncomms5254. ISSN 2041-1723. PMID 24968128.
  15. ^ Jia, Zhenhua; Zhou, Feng; Liu, Mingxin; Li, Xingshu; Chan, Albert S. C.; Li, Chao-Jun (2013-11-04). "Silver-Catalyzed Hydrogenation of Aldehydes in Water". Angewandte Chemie International Edition. 52 (45): 11871–11874. doi:10.1002/anie.201306243. PMID 24127208.
  16. ^ Wei, Chunmei; Li, Chao-Jun (2002-04-26). "Enantioselective Direct-Addition of Terminal Alkynes to Imines Catalyzed by Copper(I)pybox Complex in Water and in Toluene". Journal of the American Chemical Society. 124 (20): 5638–5639. doi:10.1021/ja026007t. PMID 12010027.
  17. ^ Yoo, Woo-Jina; Zhao, Liang; Li, Chao-Jun (2011). "The A3-Coupling (aldehyde-Alkyne-Amine) Reaction: A versatile method for the preparation of propargylamines". Aldrichimica Acta. 44: 43–51.
  18. ^ Li, Chao-Jun (2008-12-16). "Cross-Dehydrogenative Coupling (CDC): Exploring C− C Bond Formations Beyond Functional Group Transformations". Accounts of Chemical Research. 42 (2): 335–344. doi:10.1021/ar800164n. PMID 19220064.
  19. ^ Li, Lu; Fan, Shizhao; Mu, Xiaoyue; Mi, Zetian; Li, Chao-Jun (2014-06-04). "Photoinduced conversion of methane into benzene over GaN nanowires". Journal of the American Chemical Society. 136 (22): 7793–7796. doi:10.1021/ja5004119. ISSN 0002-7863. PMID 24826797.
  20. ^ Liu, Mingxin; Wang, Yichen; Kong, Xianghua; Rashid, Roksana T.; Chu, Sheng; Li, Chen-Chen; Hearne, Zoë; Guo, Hong; Mi, Zetian; Li, Chao-Jun (April 2019). "Direct catalytic methanol-to-ethanol photo-conversion via methyl carbene". Chem. 5 (4): 858–867. Bibcode:2019Chem....5..858L. doi:10.1016/j.chempr.2019.01.005.
  21. ^ Tan, Lida; Su, Hui; Han, Jingtang; Liu, Mingxin; Li, Chao-Jun (December 2022). "Selective conversion of methane to cyclohexane and hydrogen via efficient hydrogen transfer catalyzed by GaN supported platinum clusters". Scientific Reports. 12 (1): 18414. Bibcode:2022NatSR..1218414T. doi:10.1038/s41598-022-21915-9. PMC 9626580. PMID 36319805.
  22. ^ Han, Jing-Tan; Su, Hui; Tan, Lida; Li, Chao-Jun (February 2023). "In aqua dual selective photocatalytic conversion of methane to formic acid and methanol with oxygen and water as oxidants without over oxidation". iSciences. 26 (2): 105942. Bibcode:2023iSci...26j5942H. doi:10.1016/j.isci.2023.105942. PMC 9876743. PMID 36711239.
  23. ^ Wang, Haining; Dai, Xi-Jie; Li, Chao-Jun (April 2017). "Aldehydes as alkyl carbanion equivalents for additions to carbonyl compounds". Nature Chemistry. 9 (4): 374–378. doi:10.1038/nchem.2677. ISSN 1755-4330. PMID 28338683. S2CID 11653420.
  24. ^ Dai, Xijie; Li, Chenchen; Li, Chao-Jun (April 2021). "Carbonyl umpolung as organometallic reagent surrogates". Chemical Society Reviews. 50 (19): 10733–10742. doi:10.1039/D1CS00418B. PMID 34382626. S2CID 236989985.
  25. ^ Li, Chao-Jun (January 2023). "HOME-Chemistry: hydrazone as organo-metallic equivalent". Pure & Applied Chemistry. 95 (5): 465–474. doi:10.1515/pac-2022-1003.