Metal‐Free Intermolecular C−H Borylation of N‐Heterocycles at B−B Multiple Bonds
Please always quote using this URN: urn:nbn:de:bvb:20-opus-312385
- Carbene‐stabilized diborynes of the form LBBL (L=N‐heterocyclic carbene (NHC) or cyclic alkyl(amino)carbene (CAAC)) induce rapid, high yielding, intermolecular ortho‐C−H borylation at N‐heterocycles at room temperature. A simple pyridyldiborene is formed when an NHC‐stabilized diboryne is combined with pyridine, while a CAAC‐stabilized diboryne leads to activation of two pyridine molecules to give a tricyclic alkylideneborane, which can be forced to undergo a further H‐shift resulting in a zwitterionic, doubly benzo‐fusedCarbene‐stabilized diborynes of the form LBBL (L=N‐heterocyclic carbene (NHC) or cyclic alkyl(amino)carbene (CAAC)) induce rapid, high yielding, intermolecular ortho‐C−H borylation at N‐heterocycles at room temperature. A simple pyridyldiborene is formed when an NHC‐stabilized diboryne is combined with pyridine, while a CAAC‐stabilized diboryne leads to activation of two pyridine molecules to give a tricyclic alkylideneborane, which can be forced to undergo a further H‐shift resulting in a zwitterionic, doubly benzo‐fused 1,3,2,5‐diazadiborinine by heating. Use of the extended N‐heteroaromatic quinoline leads to a borylmethyleneborane under mild conditions via an unprecedented boron‐carbon exchange process.…
Author: | Tobias Brückner, Benedikt Ritschel, J. Oscar C. Jiménez‐Halla, Felipe Fantuzzi, Dario Duwe, Christian Markl, Rian D. Dewhurst, Maximilian Dietz, Holger BraunschweigORCiD |
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URN: | urn:nbn:de:bvb:20-opus-312385 |
Document Type: | Journal article |
Faculties: | Fakultät für Chemie und Pharmazie / Institut für Anorganische Chemie |
Language: | English |
Parent Title (English): | Angewandte Chemie International Edition |
Year of Completion: | 2023 |
Volume: | 62 |
Issue: | 5 |
Article Number: | e202213284 |
Source: | Angewandte Chemie International Edition 2023, 62(5):e202213284. DOI: 10.1002/anie.202213284 |
DOI: | https://doi.org/10.1002/anie.202213284 |
Dewey Decimal Classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
Tag: | Boron; Borylation; Carbene; Diboryne; Hydroarylation |
Release Date: | 2023/06/16 |
EU-Project number / Contract (GA) number: | 669054 |
OpenAIRE: | OpenAIRE |
Licence (German): | CC BY: Creative-Commons-Lizenz: Namensnennung 4.0 International |