Stille  Cross‐Coupling of a Racemic Planar‐Chiral Ferrocene and Crystallographic Trace Analysis of Catalysis Intermediates and By‐products | Zendy

Weber Immo | Zendy; Heinemann Frank W. | Zendy; Bakatselos Panagiotis | Zendy; Zenneck Ulrich | Zendy

Premium

Stille Cross‐Coupling of a Racemic Planar‐Chiral Ferrocene and Crystallographic Trace Analysis of Catalysis Intermediates and By‐products

Author(s) -

Weber Immo,

Heinemann Frank W.,

Bakatselos Panagiotis,

Zenneck Ulrich

Publication year - 2007

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.200790083

Subject(s) - chemistry , stille reaction , ferrocene , palladium , catalysis , iodobenzene , medicinal chemistry , coupling reaction , polymer chemistry , crystal structure , organic chemistry , electrochemistry , electrode

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( 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 ).

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research