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- Title
Catalytic Double Carbon-Boron Bond Formation for the Synthesis of Cyclic Diarylborinic Acids as Versatile Building Blocks for π-Extended Heteroarenes.
- Authors
Igarashi, Takuya; Tobisu, Mamoru; Chatani, Naoto
- Abstract
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, CO2Et, CONEt2 and NMeCO2 tBu. 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.
- Subjects
HETEROARENES; BORINIC acids; BOND formation mechanism; CHEMICAL synthesis; PALLADIUM compounds; AMINOBORANES
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 8, p2101
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201612535