Английская Википедия:(2-Bromophenyl)diphenylphosphine

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Шаблон:Chembox

(2-Bromophenyl)diphenylphosphine is an organophosphorus compound with the formula (CШаблон:SubHШаблон:SubBr)P(CШаблон:SubHШаблон:Sub)Шаблон:Sub. It is a white crystalline solid that is soluble in nonpolar organic solvents. The compound is used as a precursor to the 2-lithiated derivative of triphenylphosphine,[1] which in turn is a precursor to other phosphine ligands.

Preparation

The compound has been prepared by several methods.[1] An efficient route is the coupling reaction of diphenylphosphine and 2-bromoiodobenzene, which is catalyzed by palladium complexes (Ph = CШаблон:SubHШаблон:Sub):[2]

CШаблон:SubHШаблон:SubBr(I) + HPPhШаблон:Sub + EtШаблон:SubN → PhШаблон:SubP(CШаблон:SubHШаблон:SubBr) + [EtШаблон:SubNH]I

The compound is isomorphous with (2-tolyl)diphenylphosphine.[3]

Lithiation with butyl lithium gives o-lithiated triphenylphosphine. The bromide also forms a Grignard reagent. These metallated phosphines are versatile reagents.[4]

BrC6H4PPh2 + Mg → BrMgC6H4PPh2
2 BrMgC6H4PPh2 + PhPCl2 → PhP[C6H4PPh2]2 + 2 MgClBr

References

Шаблон:Reflist

  1. 1,0 1,1 Шаблон:Cite journal
  2. Шаблон:Cite journal
  3. Шаблон:Cite journal
  4. Hartley, J. G., Venanzi, L. M., Goodall, D. C., "The preparation and complex-forming properties of one tritertiary and one tetratertiary phosphine", J. Chem. Soc. 1963, 3930. Шаблон:Doi