Palladium catalyzed cross-methylation of bromoheterocycles with intramolecularly stabilized dimethyl indium reagents

Autor:	Nimer Jaber, Jochanan Blum, Herbert Schumann
Rok vydání:	2003
Předmět:	Steric effects Organic Chemistry chemistry.chemical_element General Medicine Methylation Thiophene derivatives Catalysis chemistry Reagent Polymer chemistry Electronic effect Organic chemistry Gallium Indium Palladium
Zdroj:	Journal of Heterocyclic Chemistry. 40:565-567
ISSN:	1943-5193 0022-152X
DOI:	10.1002/jhet.5570400402
Popis:	Although the intramolecularly stabilized [(3-dimethylamino)propyl]dimethylaluminum (1a) fails to undergo palladium-catalyzed cross-coupling with bromopyridines and with bromofuran derivatives, the analogous gallium and indium reagent 1b and 1c smoothly cross-methylate these and other bromoheterocycles. The cross-coupling can be performed also with the dimeric indium and gallium compounds bis(μ-[2-(dimethylamino)ethanolato-N,O:O]tetramethyldigallium and -diindium (2b and 2c, respectively). The indium reagent is fairly air-stable and the reactions can be carried out under ambient conditions. The yields are generally very high but are influenced by steric and electronic effects.
Databáze:	OpenAIRE
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