Progress on Visible-Light Promoted Addition Reactions of Inert C—H Bonds to Carbonyls

doi:10.6023/cjoc202306011

Abstract

Secondary and tertiary alcohols are important structural motifs that often exist in a large number of bioactive natural products and pharmaceuticals. Moreover, they can also be used as upstream raw material for preparation of various highly valuable chemicals. Among the existing synthetic methodologies for preparation of these compounds, the nucleophilic addition of nucleophiles to aldehydes and ketones represents one of the most operative ways. However, pre-functionalized substrates are always needed for this protocol, resulting in low efficiency and poor atom economy. The growing area of photocatalysis has provided a mild and effective approach for inert C—H bond activation. As a result, the photocatalytic straight addition of inert C—H bond to carbonyls has been developed, which affords the synthesis of secondary and tertiary alcohols in a new manner. The visible-light induced addition reaction of inert C—H bond to carbonyls was classified by three different mechanisms: reductive radical-polar crossover (RRPCO), radical-radical cross coupling as well as radical addition, and reviewed, respectively. Finally, the limitations and future developments of this research field are discussed.

Key words: secondary alcohol, tertiary alcohol, visible-light catalysis, reductive radical-polar crossover, radical-radical cross coupling, radical addition

Cite this article

Hong'en Tong, Hongyu Guo, Rong Zhou. Progress on Visible-Light Promoted Addition Reactions of Inert C—H Bonds to Carbonyls[J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 54-69.

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Fig. & Tab. 27

Scheme 1. Plausible mechanisms for the visible-light promoted addition of C—H bond into carbonyls

Scheme 2. Allylation of aldehydes enabled by synergistic visible-light and chromium catalysis

Scheme 3. Asymmetrical allylation of aldehydes enabled by synergistic visible-light and chromium catalysis

Scheme 4. Visible-light catalyzed allylation of aldehydes involving unactivated alkenes

Scheme 5. Decatungstate-catalyzed alkylation of aldehydes

Scheme 6. Proposed mechanism for the alkylation of aldehydes

Scheme 7. Synthesis of monoprotected 1,2-diols via photoredox catalytic allylation of aldehydes

Scheme 8. Visible-light promoted alkylation of aromatic aldehydes via synergistic copper/chromium catalysis

Scheme 9. Visible-light catalyzed metal-free benzylation of aldehydes and ketones

Scheme 10. β-C—H functionalization of cyclic ketones via merger of photoredox and organocatalysis

Scheme 11. Visible-light promoted rhodium-catalyzed asymmetrical β-C—H functionalization of 2-acyl imidazoles and 2-acylpyridines

Scheme 12. Visible-light promoted iridium-catalyzed asymmetrical aminoalkylation of trifluoromethyl ketones

Scheme 13. Visible-light catalyzed aminoalkylation of aromatic aldehydes

Scheme 14. Visible-light catalyzed aminoalkylation of aromatic aldehydes and ketones

Scheme 15. Visible-light catalyzed intramolecular aminoalkylation of ketones

Scheme 16. Aminoalkylation of aromatic aldehydes and ketones by photocatalytic proton-coupled electron transfer

Scheme 17. Visible-light catalyzed aminoalkylation of isatin derivatives

Scheme 18. Visible-light promoted sulfur alkylation of isatin derivatives

Scheme 19. Proposed mechanism for sulfur alkylation of isatin derivatives

Scheme 20. Visible-light promoted benzylation of isatin derivatives

Scheme 21. Visible-light promoted benzylation of 9-fluorenones

Scheme 22. Allylation of ketones enabled by synergistic visible-light and thiol catalysis

Scheme 23. Benzylation of ketones with Br－ as HAT reagent and allylation of ketones with semiconductor as photosensitizer

Scheme 24. Visible-light catalyzed allylation of α-ketoesters

Scheme 25. Visible-light catalyzed arylation of α-ketoesters

Scheme 26. Visible-light catalyzed asymmetric alkylation of 2-acyl pyridines

Scheme 27. Alkylation of ketones and aldehydes under synergistic visible-light, TPI and titanium(III) catalysis

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