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Transition‐Metal‐Free Borylation of Allylic and Propargylic Alcohols
Author(s) -
Miralles Núria,
Alam Rauful,
Szabó Kálmán J.,
Fernández Elena
Publication year - 2016
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.201511255
Subject(s) - borylation , allylic rearrangement , chemistry , lewis acids and bases , adduct , yield (engineering) , cyclohexanol , transition metal , medicinal chemistry , catalysis , organic chemistry , materials science , aryl , alkyl , metallurgy
The base‐catalyzed allylic borylation of tertiary allylic alcohols allows the synthesis of 1,1‐disubstituted allyl boronates, in moderate to high yield. The unexpected tandem performance of the Lewis acid–base adduct, [Hbase] + [MeO‐B 2 pin 2 ] − favored the formation of 1,2,3‐triborylated species from the tertiary allylic alcohols and 1‐propargylic cyclohexanol at 90 °C.