Copper-catalyzed arylation of propargyl silanes with iodanes featuring the 1,2-silyl shift
Paul Walden 14th Symposium on Organic Chemistry 2025
Rasma Kroņkalne, Māris Turks

Following our previous studies on propargyl silane functionalization,1 we now explore the arylation of propargyl silanes 1, using iodanes as formal carbon electrophiles. In the absence of a propargylic silyl group, transition metal-catalyzed (Cu, Pd) approaches typically result in terminal alkyne C(sp)–H arylation.2 In contrast, propargyl silanes, depending on C-skeleton length, undergo either 1,3- or 1,1carbodifunctionalization (Scheme 1). In substrates containing an internal nucleophile, this leads to the formation of 5-membered heterocycles 4, containing a styryl side chain, or 6-membered heterocycles 5. In the case of aliphatic propargyl silanes, an arylation - β-H elimination event occurs, leading to aryl dienes 2 and indenes 3. The introduction of a variety of (hetero)aromatic groups with electron-donating and electron-withdrawing substituents was studied for this reaction.


Atslēgas vārdi
Propargyl silanes, iodanes, copper-catalysis

Kroņkalne, R., Turks, M. Copper-catalyzed arylation of propargyl silanes with iodanes featuring the 1,2-silyl shift. No: Paul Walden 14th Symposium on Organic Chemistry, Latvija, Rīga, 25.-26. septembris, 2025. Rīga: 2025, 63.-63.lpp.

Publikācijas valoda
English (en)
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