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Expedient Hydrofunctionalisation of Carbonyls and Imines Initiated by Phosphacyclohexadienyl Anions
Author(s) -
Margeson Matthew J.,
Seeberger Felix,
Kelly John A.,
Leitl Julia,
Coburger Peter,
Szlosek Robert,
Müller Christian,
Wolf Robert
Publication year - 2021
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.202100651
Subject(s) - chemistry , hydroboration , methanol , catalysis , medicinal chemistry , organic chemistry , carbon dioxide , combinatorial chemistry
The ability of phosphacyclohexadienyl anions [Li(1‐R‐PC 5 Ph 3 H 2 )] [R=Me ( 1 a ), n Bu ( 1 b ), t Bu ( 1 c ), Ph ( 1 d ) and CH 2 SiMe 3 ( 1 e )] to initiate hydrofunctionalisation reactions was investigated and compared with simple, commercially available compounds, such as LiO t Bu, KO t Bu and n BuLi. All compounds are expedient catalysts for the hydroboration of a wide scope of substrates, ranging from aldehydes to imines and esters. In the hydroboration of carbon dioxide, however, only our system was observed to efficiently produce the desired methanol equivalents.