Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 31, Pages 7059-7066Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201300585
Keywords
Homogeneous catalysis; Azides; Phosphanes; Organophosphorus compounds
Categories
Funding
- SmartMix Program of the Netherlands Ministry of Economic Affairs
- Netherlands Ministry of Education, Culture and Science
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A Staudinger/aza-Wittig reaction sequence is described that is catalytic in phosphorus. Towards this end, the phosphane oxide is reduced in situ by diphenylsilane, which allows for substoichiometric amounts of the catalyst 5-phenyldibenzophosphole to be used. The substrate scope is investigated and benzoxazoles, benzodiazepine imidates and a 2-methoxypyrrole were successfully synthesized. These investigations show that a fast aza-Wittig reaction is required to obtain high yields.
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