A practical non-cryogenic process for the selective functionalization of bromoaryls
- Resource Type
- Authors
- Manuela Seeger-Weibel; Hans Hirt; Ruedi Haenggi; Wolfgang Marterer; Fabrice Gallou; Frank Schaefer
- Source
- Tetrahedron Letters. 49:5024-5027
- Subject
- chemistry.chemical_classification
Chemistry
Organic Chemistry
Substrate (chemistry)
chemistry.chemical_element
Biochemistry
Combinatorial chemistry
Reagent
Drug Discovery
Organic chemistry
Surface modification
Lithium
Cryogenic processor
Alkyl
- Language
- ISSN
- 0040-4039
A selective and practical bromine–metal exchange process under non-cryogenic conditions was developed by a simple modification of an existing protocol. By directly adding an alkyl lithium RLi reagent to a solution of a bromoaryl substrate ArBr and an alkylmagnesium reagent RMgX, a lithium triarylmagnesiate Ar3MgLi complex formed that allowed for various types of functionalization and more elaborate cross-coupling reactions. The simplicity and improved safety of the method represent a significant improvement over current state of the art that uses lithium trialkylmagnesiate R3MgLi complexes, and is especially advantageous for large-scale synthesis.