Photocatalyzed Formal All-Carbon [3+2] Cycloaddition of Aromatic Aldehydes with Arylethynyl Silanes

Photocatalyzed Formal All-Carbon [3+2] Cycloaddition of Aromatic Aldehydes with Arylethynyl Silanes

Herein, we report a photoinduced TBADT-catalyzed formal all-carbon [3+2] cycloaddition of aromatic aldehydes and arylethynyl silanes, which combines acyl C–H and ortho C–H activation of aromatic aldehydes, offering a new method for constructing the indanone scaffold under mild conditions. By choosin...

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Veröffentlicht in:Organic letters 2022-12, Vol.24 (51), p.9413-9418
Hauptverfasser: Mao, Yujia, Fan, Pei, Wang, Chuan
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container_title Organic letters
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creator Mao, Yujia
Fan, Pei
Wang, Chuan
description Herein, we report a photoinduced TBADT-catalyzed formal all-carbon [3+2] cycloaddition of aromatic aldehydes and arylethynyl silanes, which combines acyl C–H and ortho C–H activation of aromatic aldehydes, offering a new method for constructing the indanone scaffold under mild conditions. By choosing an appropriate silane as the precursor, one can selectively retain or remove the α-silyl group of the indanone products during the reaction. Preliminary mechanistic studies point to a reaction mechanism involving a 1,5-H shift as a key step.
doi_str_mv 10.1021/acs.orglett.2c03807
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title Photocatalyzed Formal All-Carbon [3+2] Cycloaddition of Aromatic Aldehydes with Arylethynyl Silanes
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