Arylallenes undergo hydrosulfonylation under photoredox-catalyzed conditions. The reaction gives vinyl sulfones in a regio-and diastereoselective manner, employing sodium sulfinates as the sulfonyl source and eosin Y as the photocatalyst. Indol-1-yl, pyrrol-1-yl, phenyl, and naphtylallenes might be used. Aliphatic allenes are incompatible with the reaction conditions.
The reactivity of
N
-cyanomethyl quaternary salts of 4-, 5- and 7-azaindoles towards salicylic aldehydes has been studied. The interaction of azaindolium salts with salicylic aldehydes proceeds as a base-promoted domino reaction, giving the corresponding chromenoimidazopyrrolopyridines. In the case of the 7-(cyanomethyl)-7-azaindolium salt, the reaction was found to be more sensitive, but the use of the 1-methyl-substituted salt allowed the synthesis of the desired compounds, incorporating the heterocyclic core of isogranulatimide C, a marine natural product.
A new
class of trifluoromethyl building blocks2-trifluoromethyl
allyl chlorideshave been obtained through a photoredox-catalyzed
chlorotrifluoromethylation of aryl allenes. The reaction proceeded
in a regio- and stereoselective manner. A trifluoromethylated analog
of the flunarizine drug was synthesized.
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