Photocatalytic deconstructive aliphatic carbon–carbon bond cleavage and functionalization of unactivated alcohols

Photocatalytic deconstructive aliphatic carbon–carbon bond cleavage and functionalization of unactivated alcohols

Chem Catalysis

10.1016/j.checat.2023.100530

http://dx.doi.org/10.1016/j.checat.2023.100530

Adisak Thanetchaiyakup, Kek Foo Chin, Miloš Ðokić, Philip Mark Leetiong Tan, Desmond Junjie Lin, Mitch Mathiew, Xin Zhao, Jerry Zhi Xiong Heng, Daryle Jun Xiong Toh, Xue-Wei Liu, Balamurugan Ramalingam, Han Sen Soo

15 February 2023

Thanetchaiyakup, A., Chin, K. F., Ðokić, M., Tan, P. M. L., Lin, D. J., Mathiew, M., Zhao, X., Heng, J. Z. X., Toh, D. J. X., Liu, X.-W., Ramalingam, B., & Soo, H. S. (2023). Photocatalytic deconstructive aliphatic carbon–carbon bond cleavage and functionalization of unactivated alcohols. Chem Catalysis, 3(3), 100530. https://doi.org/10.1016/j.checat.2023.100530

The one pot C–C bond cleavage and functionalization of alcohol molecules is a powerful tool for exploiting some of the most abundant substrates for organic synthesis, especially in the preparation of active pharmaceutical ingredients (APIs). Here, we used a base-metal vanadium photocatalyst and visible light for the late-stage modifications of APIs/natural products with sensitive functional groups under mild reaction conditions. In addition, we illustrate a scale-up by continuous flow in high conversion, thus demonstrating how our process can be employed to manufacture value-added products conveniently. This work can potentially be extended to the valorization of non-food biomass such as chitin and cellulose, since these polysaccharides contain many hydroxy groups that can undergo C–C bond cleavage and functionalization to form valuable bioactive compounds.

Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0)

This research / project is supported by the A*STAR - Accelerated Materials Development for Manufacturing Program - MTC Programmatic
Grant Reference no. : A1898b0043

This research / project is supported by the A*STAR - AME Individual Research Grants grants
Grant Reference no. : A2083c0050

This research / project is supported by the A*STAR - AME Individual Research Grants grants
Grant Reference no. : A1783c0002

This research / project is supported by the A*STAR - AME Individual Research Grants grants
Grant Reference no. : A20E5c0087

This research / project is supported by the Minstry of Education - Academic Research Fund Tier 1 grants
Grant Reference no. : RT 05/19

This research / project is supported by the Ministry of Education - Academic Research Fund Tier 1 grants
Grant Reference no. : RG 09/22

This research / project is supported by the Ministry of Education - Academic Research Fund Tier 1 grants
Grant Reference no. : RG 09/20

This research / project is supported by the NTU - Fifth ACE Grant
Grant Reference no. : NA

https://oar.a-star.edu.sg/communities-collections/articles/20462

2667-1093

Institute of Sustainability for Chemicals, Energy and Environment