Chemistry:Cross dehydrogenative coupling

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Cross dehydrogenative coupling (also known as CDC reaction), coined by prof. Chao-Jun Li of McGill University,[1][2][3][4] is a type of coupling reaction allowing the construction of a carbon–carbon bond[5] or C-Heteroatom bond[6] directly from C-H bonds in the presence of an oxidant, leading to the thermodynamically unfavorable formal removal of a H2 molecule. As such, CDC are couplings belonging to the C-H activation strategy.

Cross-dehydrogenative-coupling between two C-H bonds.


The key to the CDC coupling is eliminating the need for substrate prefunctionalization. Therefore, the CDC reaction has the advantages of high efficiency, Atom economy and environmental friendliness. Such reactions can be achieved or activated by transition-metal catalysis or oxidation reaction (e.g. benzoquinone, peroxides, O2, hypervalent iodine), or by either photocatalysis or electrocatalysis. The mechanism and reactivity of the CDC reactions varies dramatically depending on the substrate.[7][8] CDC reactions have been used to construct bonds between sp3-sp3, sp3-sp2, sp3-sp, sp2-sp2, sp2-sp and sp-sp C-H bonds.[9][10] The synthesis and functionalization of various nitrogen, oxygen and sulfur-containing heterocycles have also been achieved via CDC.[11]

See also

References

  1. ↑ Li, Chao-Jun (2009-02-17). "Cross-Dehydrogenative Coupling (CDC): Exploring C−C Bond Formations beyond Functional Group Transformations" (in en). Accounts of Chemical Research 42 (2): 335–344. doi:10.1021/ar800164n. ISSN 0001-4842. PMID 19220064. https://pubs.acs.org/doi/10.1021/ar800164n. 
  2. ↑ Li, Z.; Bohle, D. S.; Li, C.-J. (2006-06-13). "Cu-catalyzed cross-dehydrogenative coupling: A versatile strategy for C-C bond formations via the oxidative activation of sp3 C-H bonds" (in en). Proceedings of the National Academy of Sciences 103 (24): 8928–8933. doi:10.1073/pnas.0601687103. ISSN 0027-8424. PMID 16754869. Bibcode: 2006PNAS..103.8928L. 
  3. ↑ "Cross-Dehydrogenative Coupling" (in en). 2016-12-17. https://chem.libretexts.org/Bookshelves/Inorganic_Chemistry/Modules_and_Websites_(Inorganic_Chemistry)/Catalysis/Catalyst_Examples/Cross-Dehydrogenative_Coupling. 
  4. ↑ Li, Chao-Jun, ed (2014). From C-H to C-C Bonds. Green Chemistry Series. doi:10.1039/9781782620082. ISBN 978-1-84973-797-5. https://doi-org.proxy3.library.mcgill.ca/10.1039/9781782620082. 
  5. ↑ Yeung, Charles S.; Dong, Vy M. (2011-03-09). "Catalytic Dehydrogenative Cross-Coupling: Forming Carbon−Carbon Bonds by Oxidizing Two Carbon−Hydrogen Bonds". Chemical Reviews 111 (3): 1215–1292. doi:10.1021/cr100280d. ISSN 0009-2665. PMID 21391561. https://doi-org.proxy3.library.mcgill.ca/10.1021/cr100280d. 
  6. ↑ Krylov, Igor B.; Vil’, Vera A.; Terent’ev, Alexander O. (2015-01-20). "Cross-dehydrogenative coupling for the intermolecular C–O bond formation" (in en). Beilstein Journal of Organic Chemistry 11 (1): 92–146. doi:10.3762/bjoc.11.13. ISSN 1860-5397. PMID 25670997. PMC 4311763. https://www.beilstein-journals.org/bjoc/articles/11/13. 
  7. ↑ Tsang, Althea S.-K.; Park, Soo J.; Todd, Matthew H. (2014), Li, Chao-Jun, ed., CHAPTER 11. Mechanisms of Cross-Dehydrogenative-Coupling Reactions, Green Chemistry Series, Cambridge: Royal Society of Chemistry, pp. 254–294, doi:10.1039/9781782620082-00254, ISBN 978-1-84973-797-5, http://ebook.rsc.org/?DOI=10.1039/9781782620082-00254, retrieved 2020-10-22 
  8. ↑ Huang, Chia-Yu; Kang, Hyotaik; Li, Jianbin; Li, Chao-Jun (2019-10-18). "En Route to Intermolecular Cross-Dehydrogenative Coupling Reactions" (in en). The Journal of Organic Chemistry 84 (20): 12705–12721. doi:10.1021/acs.joc.9b01704. ISSN 0022-3263. PMID 31441304. https://pubs.acs.org/doi/10.1021/acs.joc.9b01704. 
  9. ↑ Girard, Simon A.; Knauber, Thomas; Li, Chao-Jun (2014-01-03). "The Cross-Dehydrogenative Coupling of C sp 3H Bonds: A Versatile Strategy for CC Bond Formations" (in en). Angewandte Chemie International Edition 53 (1): 74–100. doi:10.1002/anie.201304268. PMID 24214829. http://doi.wiley.com/10.1002/anie.201304268. 
  10. ↑ Scheuermann, Caroline J. (2010-03-01). "Beyond Traditional Cross Couplings: The Scope of the Cross Dehydrogenative Coupling Reaction" (in en). Chemistry: An Asian Journal 5 (3): 436–451. doi:10.1002/asia.200900487. PMID 20041458. 
  11. ↑ Srivastava, Ananya, ed (2019) (in en). Heterocycles via Cross Dehydrogenative Coupling: Synthesis and Functionalization. Singapore: Springer Singapore. doi:10.1007/978-981-13-9144-6. ISBN 978-981-13-9143-9. http://link.springer.com/10.1007/978-981-13-9144-6. 



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