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Article Dans Une Revue Organic Letters Année : 2015

Efficient Synthesis of (P-Chirogenic) o -Boronated Phosphines from sec -Phosphine 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 of sec-phosphine boranes with n-BuLi and 1,2-dibromobenzene, and then with boron reagents, afford the o-boronatophenylphosphine derivatives in 71% yields. The use of P-chirogenic sec-phosphine boranes leads to the free boronated phosphines with retention of configuration at the P-center after decomplexation. The reaction of P-chirogenic o-boronatophenylphosphine with KHF2 affords the corresponding trifluoroborated phosphine with ee >98%.


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Dates et versions

hal-03566423 , version 1 (11-02-2022)



Jérôme Bayardon, Julie Bernard, Emmanuelle Rémond, Yoann Rousselin, Raluca Malacea-Kabbara, et al.. Efficient Synthesis of (P-Chirogenic) o -Boronated Phosphines from sec -Phosphine Boranes. Organic Letters, 2015, 17 (5), pp.1216-1219. ⟨10.1021/acs.orglett.5b00167⟩. ⟨hal-03566423⟩
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