title: Racemic and enantioselective metal-catalyzed synthesis of SF5-containing diarylmethanols.
abstract: 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.
authors.affiliation: CCVC, PROTEO, Département de chimie, 1045 avenue de la Médecine, Université Laval, Québec, Québec, CanadaG1V 0A6. jean-francois.paquin@chm.ulaval.ca.
authors.forename: Justine
authors.initials: J
authors.lastname: Desroches
authors.affiliation: CCVC, PROTEO, Département de chimie, 1045 avenue de la Médecine, Université Laval, Québec, Québec, CanadaG1V 0A6. jean-francois.paquin@chm.ulaval.ca.
authors.forename: Ariane
authors.initials: A
authors.lastname: Tremblay
authors.affiliation: CCVC, PROTEO, Département de chimie, 1045 avenue de la Médecine, Université Laval, Québec, Québec, CanadaG1V 0A6. jean-francois.paquin@chm.ulaval.ca.
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Paquin