3,5-Bis(pentafluorosulfanyl)phenylboronic acid: A new organocatalyst for Conia-ene carbocyclization of 1,3-dicarbonyl compounds having terminal alkynes

3,5-Bis(pentafluorosulfanyl)phenylboronic acid 1 was introduced as an efficient organocatalyst for Conia-ene carbocyclization of 1,3-dicarbonyl compounds having terminal alkynes. A variety of 2-alkynic 1,3-dicarbonyl compounds were smoothly converted to ene-carbocyclization products in moderate to excellent yields. Compared with the reported catalyst, 3-nitro phenylboronic acid, catalyst 1 is slightly better in a non-polar solvent such as toluene and Solkane®365mfc (1,1,1,3,3-pentafluorobutane). These results indicate that the SF5 function can be a lipophilic and sterically demanding alternative to the NO2 group in catalyst design.

: 3,5-Bis(pentafluorosulfanyl)phenylboronic acid 1 was introduced as an efficient organocatalyst for Conia-ene carbocyclization of 1,3-dicarbonyl compounds having terminal alkynes. A variety of 2-alkynic 1,3-dicarbonyl compounds were smoothly converted to ene-carbocyclization products in moderate to excellent yields. Compared with the reported catalyst, 3-nitro phenylboronic acid, catalyst 1 is slightly better in a non-polar solvent such as toluene and Solkane®365mfc. These results indicate that the SF5 function can be a lipophilic and sterically demanding alternative to the NO2 group in catalyst design.Figure optionsDownload as PowerPoint slideHighlights
► Bis(pentafluorosulfanyl)phenylboronic acid is as an efficient organocatalyst.
► Bis(pentafluorosulfanyl)phenylboronic acid is a catalyst for Conia-ene reaction.
► Bis(pentafluorosulfanyl)phenylboronic acid is a catalyst for carbocyclization.
► SF5 function is a lipophilic alternative to the NO2 group.
► SF5 function is a sterically demanding alternative to the NO2 group.