Stereoselective synthesis of o-bromo (or Iodo) aryl P-chirogenic phosphines based on aryne chemistry

…, H Laureano, V Diemer, M Dutartre, U Das…

Index: Bayardon, Jerome; Laureano, Hugo; Diemer, Vincent; Dutartre, Mathieu; Das, Utpal; Rousselin, Yoann; Henry, Jean-Christophe; Colobert, Francoise; Leroux, Frederic R.; Juge, Sylvain Journal of Organic Chemistry, 2012 , vol. 77, # 13 p. 5759 - 5769

Full Text: HTML

Citation Number: 35

Abstract

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 ...