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Direct Hydroboration of BB Bonds: A Mild Strategy for the Proliferation of BB Bonds
Author(s) -
Braunschweig Holger,
Dewhurst Rian D.,
Hörl Christian,
Phukan Ashwini K.,
Pinzner Florian,
Ullrich Stefan
Publication year - 2014
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.201309325
Subject(s) - hydroboration , chemistry , boron , reagent , catalysis , combinatorial chemistry , transition metal , electron deficiency , stereochemistry , organic chemistry
Synthetic access to electron‐precise boron chains is hampered by the preferential formation of nonclassical structures. The few existing strategies for this involve either strongly reducing reagents or transition‐metal catalysts, both with distinct disadvantages. The synthesis of new furyl‐ and thienyl‐substituted diborenes is presented, along with their direct hydroboration with catecholborane (CatBH) to form a new electron‐precise BB bond and a B 3 chain. The reaction is diastereoselective and proceeds under mild conditions without the use of strong reducing agents or transition‐metal catalysts commonly used in B‐B coupling reactions.