942472-61-9Relevant academic research and scientific papers
Stille cross-coupling of a racemic planar-chiral ferrocene and crystallographic trace analysis of catalysis intermediates and by-products
Weber, Immo,Heinemann, Frank W.,Bakatselos, Panagiotis,Zenneck, Ulrich
, p. 834 - 845 (2008/03/12)
A pressure-controlled procedure for the SN1 reaction of rac-1-[(dimethylamino)methyl]-2-(tributylstannyl)ferrocene (1) to rac-1-(phthalimidomethyl)-2-(tributylstannyl)ferrocene (2) was developed. Pd0-Catalyzed Stille coupling of 2 with iodobenzene afforded rac-1-phenyl-2-(N-phthalimidomethyl)-ferrocene (5) in 74% yield; after trace enrichment by crystallization of the combined mother liquors, one single crystal of each, 5, catalysis intermediate trans-iodo(σ-phenyl) bis(triphenylarsino)palladium(II) (7), trans-diiodobis(triphenylarsino) palladium(II) (8), and rac-2,2′-bis(phthalimidomethyl)-1,1′- biferrocene (9) could be isolated by crystal sorting under a microscope and characterized by X-ray crystal structure analysis. Furthermore, 5 was deprotected to amine (11), which does even survive the Birch reduction to rac-1-(aminomethyl)-2-(cyclohexa-2,5-dienyl)ferrocene (12).
