Recent Progress in Light-Driven Direct Dehydroxylation and Derivation of Alcohols

doi:10.6023/cjoc202303036

Abstract

Conventional methods for the reduction of alcohols mainly deal with the indirect cleavages of C_sp3—O bond involving tedious activated steps. In contrast, the more straightforward direct reduction of naturally abundant aliphatic alcohols to alkanes or other reductive derivatives poses a challenge to organic chemists due to the inherently stable and less reactive C_sp3—O bond. The development of direct reductive strategies induced by light is of utmost importance due to their atom economy, step economy and redox economy, and many progresses have been made in this area these years. However, very few reviews on this topic has been reported so far. Herein, the recent progress in the light-driven direct deoxygenation of alcohols with emphasis on important advances last ten years is reviewed, which is expected to further promote the vigorous development of this field.

Key words: alcohols, reduction, alkylation, dehydroxylation, photochemistry

Cite this article

Boyu Yan, Jieliang Wu, Jinfei Deng, Dan Chen, Xiushen Ye, Qiuli Yao. Recent Progress in Light-Driven Direct Dehydroxylation and Derivation of Alcohols[J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3055-3066.

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Fig. & Tab. 26

Scheme 1. Photoinduced one-pot deoxygenation of alcohols

Scheme 2. Photocatalytic deoxygenation of alcohols via gold catalyst

Scheme 3. Photocatalytic transfer hydrogenolysis of allylic alcohols

Scheme 4. Reduction of benzylic alcohols via Ir catalyst

Scheme 5. Light-driven metal-free direct deoxygenation of ben- zyl alcohols

Scheme 6. Light-driven metal-free direct carboxylation of benzyl alcohols

Scheme 7. Carboxylation of benzylic alcohols via boryl radical

Scheme 8. Direct carboxylation of allylic alcohols by photoredox/nickel dual catalysis

Scheme 9. Photocatalytic halogenation of alcohols

Scheme 10. Photocatalytic bromination of saccharides

Scheme 11. Transformation of alcohol to iodide under visible light

Scheme 12. Halogenation of alcohols via NBS or NCS

Scheme 13. Halogenation of alcohols via NBS or NCS

Scheme 14. Photoinduced deoxyalkylation with alcohols

Scheme 15. Visible light induced deoxyalkylation with alcohols

Scheme 16. Spin-center shift-enabled enantioselective benzylation of aldehydes with alcohols

Scheme 17. NHC-mediated coupling of alcohols with aryl halide

Scheme 18. NHC-mediated coupling of alcohols with carboxylic acid derivatives

Scheme 19. Direct trifluoromethylation of alcohols

Scheme 20. Alkylation with alcohols and Michael acceptors

Scheme 21. Dehydroxylative addition of alcohols with Michael acceptors

Scheme 22. Catalyst-free dehydroxylative alkylation of unsaturated compounds with alcohols

Scheme 23. Direct alkylation with alcohols and thiols via frustrated Lewis pairs

Scheme 24. UV-light induced methylation with alcohols

Scheme 25. Visible-light induced synthesis of quinazolinone derivatives with alcohols

Scheme 26. Visible-light induced synthesis of dihydroquinazolinone or quinazolinone derivatives with alcohols

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