Issue 86, 2020

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

Abstract

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.

Graphical abstract: 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

Supplementary files

Article information

Article type
Communication
Submitted
15 Feb 2020
Accepted
21 Sep 2020
First published
21 Sep 2020

Chem. Commun., 2020,56, 13165-13168

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

S. Manna, P. K. Someswara Ashwathappa and K. R. Prabhu, Chem. Commun., 2020, 56, 13165 DOI: 10.1039/D0CC01217C

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