Triphenylbismuthine is an organobismuth compound with the formula Bi(C6H5)3. It is a white, air-stable solid that is soluble in organic solvents. It is prepared by treatment of bismuth trichloride with phenylmagnesium bromide.
BiCl3 + 3 C6H5MgBr → Bi(C6H5)3 + 3 MgBrCl Structurally it resembles related compounds such as triphenylstibine. The C-Bi-C angles are 94°. Triphenylbismuthine serves as a phenyl donor in some cross coupling reactions catalyzed by Pd(0) complexes. It reacts with trifluoromethanesulfonic acid to give bismuth triflate:
Bi(C6H5)3 + 3 HO3SCF3 → Bi(O3SCF3)3 + 3 C6H6 Triphenylbismuthine readily undergoes oxidative addition to form Bi(V) derivatives such as triphenylbismuthine dichloride.
Related compounds Triphenylphosphine Triphenylarsine Triphenylstibine
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