Synthesis of 1H-1, 3-benzazaphospholes: substituent influence and mechanistical aspects
…, N Gupta, A Surana, N Peulecke, B Witt, K Steinhauser…
Index: Heinicke, Joachim; Gupta, Nidhi; Surana, Anushka; Peulecke, Normen; Witt, Brigitte; Steinhauser, Kinga; Bansal, Raj K; Jones, Peter G Tetrahedron, 2001 , vol. 57, # 50 p. 9963 - 9972
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Citation Number: 52
Abstract
Various substituted carboxylic acid 2-chloro-and 2-bromoanilides 1a–j react with triethylphosphite in the presence of anhydrous NiCl2 or NiBr2 to give o-acylamido- benzenephosphonic acid esters 2a–g and 2j. Yields depend strongly on the substituents. 2- Fluoro-4, 6-dibromoacetanilide 1g reacts only at 6-position, indicating an o-directed process. Based on substituent effects, we infer a mechanism via Ni (0) intermediates that insert into ...
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