Chao-Jun Li Explained

Chao-Jun Li
Fields:Green chemistry, organic chemistry
Workplaces:McGill University (2003-present)Tulane University (1994–2003)
Alma Mater:Zhengzhou University (BSc)Chinese Academy of Science (MSc)
McGill University (PhD)
Stanford University (postdoctoral work)
Awards:1998 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
Academic Advisors:Tak-Hang Chan
David Harpp
Barry Trost
Website:http://www.cjlimcgill.ca/

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).

Education

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

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

Reactions in water:

A3 coupling reaction[16] [17]

Cross dehydrogenative coupling(CDC)[18]

GaN Photocatalysts

Hydrazones as organo-metallic equivalent (HOME Chemistry):

Notes and References

  1. 2005. New Associate Editor – The Americas. Green Chemistry. 7. 2. 58. 10.1039/B500233H.
  2. Web site: Canada Research Chairs . Government of Canada. Industry Canada . 2012-11-29. www.chairs-chaires.gc.ca. 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 . 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. 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. 10.1016/0040-4020(95)01056-4.
  6. Web site: A breakthrough for organic reactions in water. ScienceDaily. 2020-04-17.
  7. Web site: Simple hydrogen storage solution is powered by solar energy . phys.org. 2020-04-17.
  8. Web site: Service. Robert F.. 19 February 2019 . Ultraviolet light could provide a powerful new source of green fuel. Science. live . https://web.archive.org/web/20190219212212/http://www.sciencemag.org/news/2019/02/ultraviolet-light-could-provide-powerful-new-source-green-fuel . 2019-02-19 .
  9. Web site: Carbanion analogs derived from naturally-occurring aldehydes. phys.org. 2020-04-17.
  10. Web site: Palladium-catalyzed Deoxygenative Amination Of Phenols. Science Trends. 2017-12-04. 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. 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. 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 . 10.1021/ja029649p. 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 . 10.1038/ncomms5254. 24968128. 2014NatCo...5.4254Z. 2041-1723. free.
  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 . 10.1002/anie.201306243. 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. 10.1021/ja026007t. 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. 10.1021/ar800164n. 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. 10.1021/ja5004119. 24826797. 0002-7863.
  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. 10.1016/j.chempr.2019.01.005 . free. 2019Chem....5..858L .
  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. 10.1038/s41598-022-21915-9 . 36319805 . 9626580 . 2022NatSR..1218414T . free.
  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. 10.1016/j.isci.2023.105942. 36711239 . 9876743 . 2023iSci...26j5942H . free.
  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. 10.1038/nchem.2677. 28338683 . 11653420. 1755-4330.
  24. Dai. Xijie. Li. Chenchen. Li. Chao-Jun. April 2021. Carbonyl umpolung as organometallic reagent surrogates. Chemical Society Reviews. 50 . 19 . 10733–10742 . 10.1039/D1CS00418B. 34382626 . 236989985.
  25. Li. Chao-Jun. January 2023. HOME-Chemistry: hydrazone as organo-metallic equivalent. Pure & Applied Chemistry. 95. 5. 465–474. 10.1515/pac-2022-1003. free.