Photo-Catalyzed Synthesis of Indanones from Aromatic Aldehydes and Terminal Alkynes
Florence Babawale1, Indrajit Ghosh1, Burkhard König1
1Fakultät für Chemie und Pharmazie, Universität Regensburg, Regensburg 93040, Germany.
Abstract:
Indanones are key structural motifs in pharmaceuticals and bioactive natural products, making their efficient synthesis a subject of continued interest. Conventional methods typically rely on transition-metal catalysis, prefunctionalized substrates, and multiple redox steps. Herein, we report a photochemical C-H annulation strategy for the direct synthesis of indanones from simple, unmodified aromatic aldehydes and terminal alkynes. The reaction proceeds under 365 nm light using tetrabutylphosphonium decatungstate ([Bu4P]4W10O32, TBPDT) as a hydrogen atom transfer (HAT) photocatalyst. This prefunctionalization-free protocol tolerates a broad range of substrates, eliminates the need for additional redox steps, and expands the toolbox for sustainable indanone synthesis.
More Related Videos
Related Concept Videos
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Preparation of Alkynes: Dehydrohalogenation
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation


