One-Pot Regio-\nand Diastereoselective Gold-Catalyzed\nPropargylation of in Situ Activated Chromones and Consecutive Cyclization

Herein, we report a gold-catalyzed propargylation of\nchromone derivatives\nby propargylsilanes. Chromones are synergistically activated by the\nsilylium cation resulting from the gold activation of the propargylsilane.\nThe reaction exclusively occurs at the C2-position of the chromone,\nand a single diastereoisomer is formed. Computational studies performed\non the reaction mechanism rationalize the formation of the preferred\ndiastereoisomer. Finally, a dual consecutive cascade reaction based\non different gold catalysts enables the formation of complex tricyclic\ncompounds.

Publication Details

Journal
Figshare
Published
2024-11-28
DOI
https://doi.org/10.1021/acs.orglett.4c03812.s001
Primary Topic
Catalytic Alkyne Reactions
Type
article
Field-Weighted Citation Impact
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article

One-Pot Regio-\nand Diastereoselective Gold-Catalyzed\nPropargylation of in Situ Activated Chromones and Consecutive Cyclization

Figshare
Catalytic Alkyne Reactions
article

One-Pot Regio-\nand Diastereoselective Gold-Catalyzed\nPropargylation of in Situ Activated Chromones and Consecutive Cyclization

article en

Abstract

Herein, we report a gold-catalyzed propargylation of\nchromone derivatives\nby propargylsilanes. Chromones are synergistically activated by the\nsilylium cation resulting from the gold activation of the propargylsilane.\nThe reaction exclusively occurs at the C2-position of the chromone,\nand a single diastereoisomer is formed. Computational studies performed\non the reaction mechanism rationalize the formation of the preferred\ndiastereoisomer. Finally, a dual consecutive cascade reaction based\non different gold catalysts enables the formation of complex tricyclic\ncompounds.

Figshare
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Catalytic Alkyne Reactions
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One-Pot Regio-\nand Diastereoselective Gold-Catalyzed\nPropargylation of in Situ Activated Chromones and Consecutive Cyclization · Figshare (2024) | TGRS Research Map | TGRS