The Group 14 (Si, Ge, and Sn), Group 15 (P, As, Sb, and Bi), and Group 16 (Se and Te) 2-trimethylsilyl-1-benzometalloles (7) were prepared by the reaction of the corresponding metal reagents with beta,o-dilithio-beta-trimethylsilylstyrene intermediate (6), which was derived from phenylacetylene or o-bromoiodobenzene via three steps. The trimethylsilyl group in 7 could be readily removed by treatment with tetrabutylammonium fluoride to give the C-unsubstituted 1-benzometalloles (10).