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Copper‐Catalyzed [3+2] Cycloaddition Reactions of Isocyanoacetates with Phosphaalkynes to Prepare 1,3‐Azaphospholes
Author(s) -
Liang Wenbin,
Nakajima Kazunari,
Sakata Ken,
Nishibayashi Yoshiaki
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201812779
Subject(s) - cycloaddition , chemistry , catalysis , copper , bromide , potassium carbonate , selectivity , methane , potassium , carbonate , medicinal chemistry , inorganic chemistry , organic chemistry
A novel copper‐catalyzed synthetic method is described for phosphorous‐ and nitrogen‐containing heterocycles such as 1,3‐azaphospholes. Cycloaddition reactions of various isocyanoacetates with phosphaalkynes in the presence of copper bromide, bis(diphenylphosphino)methane (dppm), and potassium carbonate afford the corresponding 1,3‐azaphospholes in high yields with complete selectivity. Some dppm‐bridged dicopper complexes were identified as active species for the formation of 1,3‐azaphospholes.