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Catalytic Double Carbon–Boron Bond Formation for the Synthesis of Cyclic Diarylborinic Acids as Versatile Building Blocks for π‐Extended Heteroarenes
Author(s) -
Igarashi Takuya,
Tobisu Mamoru,
Chatani Naoto
Publication year - 2017
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.201612535
Subject(s) - reagent , boron , catalysis , combinatorial chemistry , chemistry , carbon fibers , organic chemistry , materials science , composite number , composite material
The first catalytic synthesis of cyclic diarylborinic acids is developed using a dihydroaminoborane reagent as the boron source. Unlike previously reported methods that use organolithium reagents, this method allows the easy synthesis of cyclic diarylborinic acids bearing a range of functionalities including CN, CO 2 Et, CONEt 2 and NMeCO 2 t Bu. Furthermore, these cyclic diarylborinic acids provide rapid access to skeletal diversity, in particular they enable the synthesis of six‐ to nine‐membered π‐extended heteroarenes through simple cross‐coupling reactions, which are important synthetic targets in both advanced materials and pharmaceuticals.