Visible light-mediated ipso -annulation of activated alkynes: access to 3-alkylated spiro[4,5]-trienones, thiaspiro[4,5]-trienones and azaspiro[4,5]-trienones

A novel method for chemoselective difunctionalization of activated alkynes for synthesizing 3-alkylated spiro[4,5]-trienones, thiaspiro[4,5]-trienones and spirolactams has been uncovered using photoredox catalysis under visible light conditions. The rarely used tricarbonyl compounds in photoredox ca...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2020-11, Vol.56 (86), p.13165-13168
Main Authors: Manna, Sabyasachi, Someswara Ashwathappa, Puneeth Kumar, Prabhu, Kandikere Ramaiah
Format: Article
Language:English
Subjects:
Alkylation
Alkynes
Catalysis
Chemical reactions
Crystallography
Functional groups
NMR
Nuclear magnetic resonance
Photoredox catalysis
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Summary:A novel method for chemoselective difunctionalization of activated alkynes for synthesizing 3-alkylated spiro[4,5]-trienones, thiaspiro[4,5]-trienones and spirolactams has been uncovered using photoredox catalysis under visible light conditions. The rarely used tricarbonyl compounds in photoredox catalysis were used as the alkylating source. A remarkable functional group tolerance was observed, and the application of the method has been showcased by transforming tricarbonylated spirolactams to their corresponding monocarbonylated products, which are difficult to access using traditional methods.
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc01217c