Novel Class of Tertiary Phosphine Ligands Based on a Phospha-adamantane Framework and Use in the Suzuki Cross-Coupling Reactions of Aryl Halides under Mild Conditions

Autor:	George Adjabeng, Alfredo Capretta, Tim Brenstrum, Christopher S. Frampton, Jeff Wilson, Al Robertson, James McNulty, John H. Hillhouse
Rok vydání:	2003
Předmět:	Steric effects Aryl Adamantane Organic Chemistry Halide General Medicine Alkylation Biochemistry Combinatorial chemistry Coupling reaction Catalysis chemistry.chemical_compound chemistry Organic chemistry Physical and Theoretical Chemistry Phosphine
Zdroj:	Organic Letters. 5:953-955
ISSN:	1523-7052 1523-7060
Popis:	[reaction: see text] A new class of sterically hindered phosphines based on a phospha-adamantane framework is described. Arylation or alkylation of the 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phospha-adamantane system allows for the preparation of tertiary phosphines suitable for use in palladium-catalyzed cross-coupling reactions. For example, use of a catalytic system incorporating Pd(2)(dba)(3) and 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phenyl-6-phospha-adamantane is shown to promote the Suzuki cross-coupling of aryl iodides, bromides, and activated chlorides with a variety of aryl boronic acids at room temperature in a few hours with high yields.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::3afbac8edd0e2c5ce557cd58a7f1da77 https://doi.org/10.1021/ol0341647 Zobrazit plný text záznamu