Triphenylbismuthine

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 C6H5MgBr3 ->  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