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Issue 37, 2016
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Racemic and enantioselective metal-catalyzed synthesis of SF5-containing diarylmethanols

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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.

Graphical abstract: Racemic and enantioselective metal-catalyzed synthesis of SF5-containing diarylmethanols

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Supplementary files

Article information


Submitted
02 Aug 2016
Accepted
18 Aug 2016
First published
30 Aug 2016

Org. Biomol. Chem., 2016,14, 8764-8780
Article type
Paper

Racemic and enantioselective metal-catalyzed synthesis of SF5-containing diarylmethanols

J. Desroches, A. Tremblay and J. Paquin, Org. Biomol. Chem., 2016, 14, 8764
DOI: 10.1039/C6OB01663D

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