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Synthesis 2008(19): 3040-3042  
DOI: 10.1055/s-2008-1067265
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Facile Synthesis of Steroidal Primary Amides via Palladium-Catalyzed Aminocarbonylation of Steroidal Alkenyl Halides

János Balogha, Sándor Mahób, Viktor Hádab, László Kollárc, Rita Skoda-Földes*a
a University of Pannonia, Institute of Chemistry, Department of Organic Chemistry, P. O. Box 158, 8201 Veszprém, Hungary
Fax: +36(88)624469; e-Mail: skodane@almos.uni-pannon.hu;
b Chemical Works of Gedeon Richter Ltd., P.O. Box 27, 1475 Budapest 10, Hungary
c University of Pécs, Department of Inorganic Chemistry, P. O. Box 266, 7624 Pécs, Hungary
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Publication History

Received 5 March 2008
Publication Date:
05 September 2008 (online)

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Abstract

A new method for the synthesis of primary amides from alkenyl iodides in one carbonylation step using ammonium carbamate as ammonia synthon is reported. The products were obtained in good yields under mild reaction conditions using CO (1-6 bar). Steroidal substrates with various moieties (e.g., 6-OH group, lactams, or aromatic A-ring) could be converted selectively into the products.

Key words

primary amides - carbonylations - steroids - palladium - homogeneous catalysis