Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 13, Pages 5759-5769Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo300910w
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- CNRS (Centre National de la Recherche Scientifique)
- Ministere de l'Education Nationale et de la Recherche
- Conseil Regional de Bourgogne
- Agence Nationale pour la Recherche [07BLAN292-01 MetChirPhos]
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The efficient synthesis of chiral or achiral tertiary phosphines bearing an o-bromo (or iodo)aryl substituent is described. The key step of this synthesis is based on the reaction of a secondary phosphine borane with the 1,2-dibromo (or diiodo)arene, owing to the formation in situ of an aryne species in the presence of n-butyllithium. When P-chirogenic secondary phosphine boranes were used, the corresponding o-halogeno-arylphosphine boranes were obtained without racemization in moderate to good yields and with ee up to 99%. The stereochemistry of the reaction, with complete retention of the configuration at the P atom, has been established by X-ray structures of P-chirogenic o-halogenophenyl phosphine borane complexes. The decomplexation of the borane was easily achieved without racemization using DABCO to obtain the free o-halogeno-arylphosphines in high yields.
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