Cross dehydrogenative coupling explained

Cross dehydrogenative coupling (also known as CDC reaction), coined by 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.

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] 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.[8] [9] The synthesis and functionalization of various nitrogen, oxygen and sulfur-containing heterocycles have also been achieved via CDC.[10]

See also

Notes and References

  1. Li. Chao-Jun. 2009-02-17. Cross-Dehydrogenative Coupling (CDC): Exploring C−C Bond Formations beyond Functional Group Transformations. Accounts of Chemical Research. en. 42. 2. 335–344. 10.1021/ar800164n. 19220064. 0001-4842.
  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. Proceedings of the National Academy of Sciences. en. 103. 24. 8928–8933. 10.1073/pnas.0601687103. 0027-8424. 1482542. 16754869. 2006PNAS..103.8928L. free .
  3. Web site: 2016-12-17. Cross-Dehydrogenative Coupling. 2020-10-22. Chemistry LibreTexts. en.
  4. Book: 2014. Li. Chao-Jun. From C-H to C-C Bonds. Green Chemistry Series. 10.1039/9781782620082. 978-1-84973-797-5. 1757-7047.
  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. 10.1021/cr100280d. 21391561. 0009-2665.
  6. Krylov. Igor B.. Vil’. Vera A.. Terent’ev. Alexander O.. 2015-01-20. Cross-dehydrogenative coupling for the intermolecular C–O bond formation. Beilstein Journal of Organic Chemistry. en. 11. 1. 92–146. 10.3762/bjoc.11.13. 1860-5397. 4311763. 25670997.
  7. Huang. Chia-Yu. Kang. Hyotaik. Li. Jianbin. Li. Chao-Jun. 2019-10-18. En Route to Intermolecular Cross-Dehydrogenative Coupling Reactions. The Journal of Organic Chemistry. en. 84. 20. 12705–12721. 10.1021/acs.joc.9b01704. 31441304. 201617266 . 0022-3263.
  8. 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. Angewandte Chemie International Edition. en. 53. 1. 74–100. 10.1002/anie.201304268. 24214829.
  9. Scheuermann. Caroline J.. 2010-03-01. Beyond Traditional Cross Couplings: The Scope of the Cross Dehydrogenative Coupling Reaction. Chemistry: An Asian Journal. en. 5. 3. 436–451. 10.1002/asia.200900487. 20041458. free.
  10. Book: Heterocycles via Cross Dehydrogenative Coupling: Synthesis and Functionalization. 2019. Springer Singapore. 978-981-13-9143-9. Srivastava. Ananya. Singapore. en. 10.1007/978-981-13-9144-6. 201623590. Jana. Chandan K..

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