Stereoselective Synthesis of P-Chirogenic Dibenzophosphole-Boranes via Aryne Intermediates
A new aryne-mediated tandem cross-coupling/P-cyclization sequence starting from tertiary phosphine-boranes and 1,2-dibromobenzenes is reported. P-chirogenic dibenzophospholes become accessible in a regio-, chemo-, and diastereoselective way.
Stereoselective synthesis of o-bromo (or iodo)aryl P-chirogenic phosphines based on aryne chemistry.
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-halogenopheny…
CCDC 868765: Experimental Crystal Structure Determination
Related Article: Vincent Diemer, Anaïs Berthelot, Jérôme Bayardon, Sylvain Jugé, Frédéric R. Leroux, and Françoise Colobert|2012|J.Org.Chem.|77|6117|doi:10.1021/jo3009098
CCDC 868764: Experimental Crystal Structure Determination
Related Article: Vincent Diemer, Anaïs Berthelot, Jérôme Bayardon, Sylvain Jugé, Frédéric R. Leroux, and Françoise Colobert|2012|J.Org.Chem.|77|6117|doi:10.1021/jo3009098
CCDC 868766: Experimental Crystal Structure Determination
Related Article: Vincent Diemer, Anaïs Berthelot, Jérôme Bayardon, Sylvain Jugé, Frédéric R. Leroux, and Françoise Colobert|2012|J.Org.Chem.|77|6117|doi:10.1021/jo3009098
CCDC 868763: Experimental Crystal Structure Determination
Related Article: Vincent Diemer, Anaïs Berthelot, Jérôme Bayardon, Sylvain Jugé, Frédéric R. Leroux, and Françoise Colobert|2012|J.Org.Chem.|77|6117|doi:10.1021/jo3009098
CCDC 868767: Experimental Crystal Structure Determination
Related Article: Vincent Diemer, Anaïs Berthelot, Jérôme Bayardon, Sylvain Jugé, Frédéric R. Leroux, and Françoise Colobert|2012|J.Org.Chem.|77|6117|doi:10.1021/jo3009098
CCDC 868769: Experimental Crystal Structure Determination
Related Article: Vincent Diemer, Anaïs Berthelot, Jérôme Bayardon, Sylvain Jugé, Frédéric R. Leroux, and Françoise Colobert|2012|J.Org.Chem.|77|6117|doi:10.1021/jo3009098
CCDC 868768: Experimental Crystal Structure Determination
Related Article: Vincent Diemer, Anaïs Berthelot, Jérôme Bayardon, Sylvain Jugé, Frédéric R. Leroux, and Françoise Colobert|2012|J.Org.Chem.|77|6117|doi:10.1021/jo3009098