1402070-43-2Relevant articles and documents
Racemic and enantioselective metal-catalyzed synthesis of SF5-containing diarylmethanols
Desroches, Justine,Tremblay, Ariane,Paquin, Jean-Fran?ois
, p. 8764 - 8780 (2016/10/03)
The racemic and enantioselective metal-catalyzed addition of arylboronic acids to 4- and 3-(pentafluorosulfur)benzaldehydes is reported. The racemic synthesis was accomplished using a Pd-based system and a wide range of arylboronic acids could be used, resulting in yields of 42 to 98% of the corresponding SF5-containing diarylmethanols. A ruthenium-based system, along with (R,R)-Me-BIPAM as the chiral ligand, was investigated and optimized for the enantioselective version. In this case, while the chiral SF5-containing diarylmethanols were generally obtained in good yields (up to 94%) and enantioselectivities (up to 98% ee), limitations were also observed. For instance, 4-(pentafluorosulfur)benzaldehyde generally provided slightly better yields than 3-(pentafluorosulfur)benzaldehyde. In addition, lower yields and enantioselectivities were observed when using either 4- and 3-substituted arylboronic acids bearing electron-withdrawing (e.g., CO2Et, NO2, CF3) or 2-substituted arylboronic acids (regardless of the nature of the substituent). Overall, the SF5-containing diarylmethanols described herein represent novel and potentially useful fluorinated building blocks for the synthesis of biologically active compounds.
Preparations and reactions of SF5-substituted aryl and heteroaryl derivatives via Mg and Zn organometallics
Frischmuth, Annette,Unsinn, Andreas,Groll, Klaus,Stadtmueller, Heinz,Knochel, Paul
supporting information; experimental part, p. 10234 - 10238 (2012/10/08)
Polyfunctional SF5-substituted cycles: Several organometallic sequences using zinc, copper, and magnesium intermediates were developed to prepare a broad range of SF5-substituted aromatic and heterocyclic compounds of potential interest for pharmaceutical applications. Copyright
