Efficient Synthesis of (P-Chirogenic) o-Boronated Phosphines from sec-Phosphine Boranes

• DOI: 10.1021/acs.orglett.5b00167
• Publication Date: 2015-02-13T18:33:03Z
• Authors: Jérôme Bayardon; Julie Bernard; Emmanuelle Rémond; Yoann Rousselin; Raluca Malacea-Ka...; Sylvain Jugé
• Keywords: Boranes

An efficient synthesis of boronated phosphines with an o-phenylene-bridge prepared from sec-phosphine boranes and using benzyne chemistry is reported. Successive reactions n-BuLi 1,2-dibromobenzene, then boron reagents, afford the o-boronatophenylphosphine derivatives in 71% yields. The use P-chirogenic leads to free retention configuration at P-center after decomplexation. reaction KHF2 affords corresponding trifluoroborated phosphine ee >98%.