Palladium(II)-Catalyzed Desymmetrization of 2-Alkynylbenzoate-Tethered Cyclohexadienones for the Synthesis of Polycyclic Compounds

Pd-catalyzed cascade cyclization of 2-alkynylbenzoate-tethered cyclohexadienone was developed for the single step synthesis of isocoumarin-fused dihydrochromenones. This highly atom economical method proceeds via 6-<i>endo-dig</i> cyclization of <i>tert</i>-butyl benzoate with a tethered alkyne. By modulating the reaction solvent and metal catalyst, the methodology was diverted for the purposeful synthesis of either of the <i>E/Z</i> tetra-substituted alkenes.

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Publication Details

Journal
Organic Letters
Published
2025-05-17
DOI
https://doi.org/10.1021/acs.orglett.5c01396
Citations
3
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
2.81

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article

Palladium(II)-Catalyzed Desymmetrization of 2-Alkynylbenzoate-Tethered Cyclohexadienones for the Synthesis of Polycyclic Compounds

Gamidi Rama Krishna, Kumar Vanka, Archana Rai, Priyam Bajpai et al.
3 citations
Organic Letters
Catalytic C–H Functionalization Methods
2.81
article

Palladium(II)-Catalyzed Desymmetrization of 2-Alkynylbenzoate-Tethered Cyclohexadienones for the Synthesis of Polycyclic Compounds

Gamidi Rama Krishna, Kumar Vanka, Archana Rai, Priyam Bajpai, Utpal Das
article en
3 citations

Abstract

Pd-catalyzed cascade cyclization of 2-alkynylbenzoate-tethered cyclohexadienone was developed for the single step synthesis of isocoumarin-fused dihydrochromenones. This highly atom economical method proceeds via 6-<i>endo-dig</i> cyclization of <i>tert</i>-butyl benzoate with a tethered alkyne. By modulating the reaction solvent and metal catalyst, the methodology was diverted for the purposeful synthesis of either of the <i>E/Z</i> tetra-substituted alkenes.

Organic LettersVol. 27(21)
National Chemical Laboratory (IN), Academy of Scientific and Innovative Research (IN)
Council of Scientific and Industrial Research, India, Science and Engineering Research Board
Openalex Percentile: Top 11%
Catalytic C–H Functionalization Methods
2.81
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