Racemic and enantioselective metal-catalyzed synthesis of SF5-containing diarylmethanolsElectronic supplementary information (ESI) available. CCDC 1497178. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6ob01663d

• Main Authors: Desroches, Justine, Tremblay, Ariane, Paquin, Jean-François
• Format: Journal Article
• Published: 21.09.2016
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/c6ob01663d

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 SF 5 -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 SF 5 -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. , CO 2 Et, NO 2 , CF 3 ) or 2-substituted arylboronic acids (regardless of the nature of the substituent). Overall, the SF 5 -containing diarylmethanols described herein represent novel and potentially useful fluorinated building blocks for the synthesis of biologically active compounds. The first racemic and enantioselective metal-catalyzed addition of arylboronic acids to 4- and 3-(pentafluorosulfur)benzaldehydes is reported.