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

[CHIM] Chemical Sciences 01 natural sciences 3. Good health 0104 chemical sciences
DOI: 10.1021/acs.orglett.5b00167 Publication Date: 2015-02-13T18:33:03Z
ABSTRACT
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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