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Synfacts 2005(3): 0299-0299  
DOI: 10.1055/s-2005-916143
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Negishi Cross Coupling Route to N-Unsubstituted α,α-Difluorohomophthalimides

Contributor(s): Victor Snieckus, Farhad Nowrouzi
Y. Pan, C. P. Holmes*, D. Tumelty
Affymax, Inc., Palo Alto, USA
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Publication History

Publication Date:
22 November 2005 (online)

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Significance

The preparation of α,α-difluorohomophthalimides by Cu(I)-catalyzed cross coupling of 2-haloterephthalamides with the α,α-di­fluoro Reformatsky reagent is reported. The reaction proceeds in good to excellent yields (70-93%) under mild conditions for a variety of
2-iodoarylamides bearing diverse functionalities and represents a non-F+ approach for the synthesis of fluorinated heterocyclic compounds.