1383686-39-2Relevant academic research and scientific papers
Stereoselective synthesis of o-bromo (or iodo)aryl P-chirogenic phosphines based on aryne chemistry
Bayardon, Jerome,Laureano, Hugo,Diemer, Vincent,Dutartre, Mathieu,Das, Utpal,Rousselin, Yoann,Henry, Jean-Christophe,Colobert, Francoise,Leroux, Frederic R.,Juge, Sylvain
experimental part, p. 5759 - 5769 (2012/08/08)
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.
