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Chemoselective Deoxygenation of 2° Benzylic Alcohols through a Sequence of Formylation and B(C 6 F 5 ) 3 ‐Catalyzed Reduction
Author(s) -
Richter Sven C.,
Oestreich Martin
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100148
Subject(s) - deoxygenation , chemistry , formylation , catalysis , formate , sequence (biology) , diol , medicinal chemistry , primary (astronomy) , organic chemistry , biochemistry , physics , astronomy
A sequence of formylation and B(C 6 F 5 ) 3 ‐catalyzed reduction of the resulting formate with Et 3 SiH enables the chemoselective deoxygenation of secondary benzylic alcohols. Primary benzylic and tertiary non‐benzylic alcohols are not reduced by this protocol. The formyl group fulfills a double role as activator and self‐sacrificing protecting group. The deoxygenation of these formates is fast and can be carried out in the presence of other potentially reducible groups. Neighboring‐group participation was found in the deoxygenation of certain diol motifs.