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Silyl Anion Initiated Hydroboration of Aldehydes and Ketones
Author(s) -
Stanford Martin W.,
Bismuto Alessandro,
Cowley Michael J.
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202000897
Subject(s) - hydroboration , chemistry , silylation , hydride , catalysis , borohydride , nucleophile , hydrosilylation , reactivity (psychology) , organic chemistry , substrate (aquarium) , ketone , medicinal chemistry , metal , medicine , oceanography , alternative medicine , pathology , geology
Hydroboration is an emerging method for mild and selective reduction of carbonyl compounds. Typically, transition‐metal or reactive main‐group hydride catalysts are used in conjunction with a mild reductant such as pinacolborane. The reactivity of the main‐group catalysts is a consequence of the nucleophilicity of their hydride ligands. Silicon hydrides are significantly less reactive and are therefore not efficient hydroboration catalysts. Here, a readily prepared silyl anion is reported to be an effective initiator for the reduction of aldehydes and ketones requiring mild conditions, low catalyst loadings and with a good substrate scope. The silyl anion it is shown to activate HBpin to generate a reactive borohydride in situ which reacts with aldehydes and ketones to afford the hydroboration product.