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FLP‐Catalyzed Transfer Hydrogenation of Silyl Enol Ethers
Author(s) -
Khan Imtiaz,
ReedBerendt Benjamin G.,
Melen Rebecca L.,
Morrill Louis C.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201808800
Subject(s) - silylation , enol , chemistry , catalysis , ammonia borane , borane , yield (engineering) , organic chemistry , transfer hydrogenation , ruthenium , materials science , hydrogen production , metallurgy
Herein we report the first catalytic transfer hydrogenation of silyl enol ethers. This metal free approach employs tris(pentafluorophenyl)borane and 2,2,6,6‐tetramethylpiperidine (TMP) as a commercially available FLP catalyst system and naturally occurring γ‐terpinene as a dihydrogen surrogate. A variety of silyl enol ethers undergo efficient hydrogenation, with the reduced products isolated in excellent yields (29 examples, 82 % average yield).
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