Heinemann FW (2007)
Publication Status: Published
Publication Type: Journal article
Publication year: 2007
Publisher: WILEY-V C H VERLAG GMBH
Book Volume: 90
Pages Range: 834-845
Journal Issue: 4
A pressure-controlled procedure for the S(N)1 reaction of rac-1-[(dimethylamino)methyl]-2-(tributylstannyl)ferrocene (1) to rac-1-(phthalimidomethyl)-2-(tributylstannyl)ferrocene (2) was developed. Pd-0-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(sigma-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).
APA:
Heinemann, F.W. (2007). Stille cross-coupling of a racemic planar-chiral ferrocene and crystallographic trace analysis of catalysis intermediates and by-products. Helvetica Chimica Acta, 90(4), 834-845.
MLA:
Heinemann, Frank Wilhelm. "Stille cross-coupling of a racemic planar-chiral ferrocene and crystallographic trace analysis of catalysis intermediates and by-products." Helvetica Chimica Acta 90.4 (2007): 834-845.
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