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Di(isopropylprenyl)borane: A New Hydroboration Reagent for the Synthesis of Alkyl and Alkenyl Boronic Acids
Author(s) -
Kalinin Alexey V.,
Scherer Stefan,
Snieckus Victor
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200351312
Subject(s) - hydroboration , chemistry , boranes , borane , reagent , organic chemistry , alkyl , reactivity (psychology) , hydrolysis , selectivity , combinatorial chemistry , boron , catalysis , medicine , alternative medicine , pathology
The best of the old : The new hydroboration reagent 1 combines the selectivity of disiamylborane ( 2 ) with the reactivity towards carbonyls of allyl boranes 3 . Conventional oxidative workup conditions are avoided, as facile hydrolysis in protic media provides the corresponding boronic acids with up to 99 % anti‐Markovnikov selectivities. A one‐pot hydroboration/Suzuki–Miyaura protocol adds to the synthetic value of 1 .