Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 144, Issue 1, Pages 599-605Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c11902
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- NIH [GM146248]
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This report describes a new method for the selective catalytic isomerization of cis-1,2-diols using a silanethiol catalyst. The method is highly chemoselective and tolerant to a wide range of functional groups, providing a concise route to trans-diol products. Mechanistic studies suggest that the isomerization proceeds through a reversible hydrogen atom transfer pathway mediated by the silanethiol catalyst.
Here, we report the selective, catalytic isomerization of cis-1,2-diols to trans-diequatorial-1,2-diols. The method employs triphenylsilanethiol (Ph3SiSH) as a catalyst and proceeds under mild conditions in the presence of a photoredox catalyst and under blue light irradiation. The method is highly chemoselective, broadly functional group tolerant and provides concise access to trans-diol products which are not readily obtained using other methods. Mechanistic studies reveal that isomerization proceeds through a reversible hydrogen atom transfer pathway mediated by the silanethiol catalyst.
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