Synfacts 2005(2): 0265-0265  
DOI: 10.1055/s-2005-916100
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Solid-Phase Synthesis of Cyclohexadienyl Amides

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Takayasu Arakawa
H. Gradén, T. Olsson, N. Kann*
Chalmer University of Technology, Sweden, and AstraZeneca R&D Mölndal, Sweden
Further Information

Publication History

Publication Date:
25 October 2005 (online)

Significance

Iron-mediated coupling reactions were demonstrated on polystyrene (PS) resin for the preparation of cyclohexadienyl amides. Thus, treatment of a PS-supported cationic iron cyclohexadienyl complex 3 with a variety of nucleophiles such as electron-rich aromatics, amines, alcohols, and a phosphite in the presence of i-Pr2EtN in CH2Cl2 at room temperature for 16 hours gave complexes 4. These resulting complexes 4 were converted via cleavage of PS supports with amines and removal of iron carbonyl with alkaline H2O2 into cyclohexadienyl amides 5 of 54-100% purity with 9-56% overall yields (18 examples).