1. For reviews on the synthetic utility of vinylic selenides/tellurides and vinylic phosphonates, see: (a) Comasseto, J. V.; Ling, L. W.; Stefani, H. A.; Petragnani, N. Synthesis 1997, 373.
2. (b) Minami, T.; Motoyoshiya, J. Synthesis 1992, 333.
3. Tanaka, M.; Choi, N.; Han, L. J. Am. Chem. Soc. 1996, 118, 7000.
4. Oh, D. Y.; Gil, J. M.; Sung, J. W.; Park, C. P. Synth. Commun. 1997, 27, 3171.
5. Typical procedure: To a solution of RYNa [generated in situ from R2YYR2 (1.0 mmol) and NaBH4 (2.2 mmol)] in absolute ethanol (10 mL) the 1-alkynylphosphonate 1 (2.0 mmol) was added dropwise at room temperature. The reaction mixture was stirred for the time indicated in Table 1. Then the mixture was poured into a saturated aqueous solution of NH4Cl (10 mL) and the aqueous layer was extracted with ethyl acetate (2×25 mL). The organic layer was dried (MgSO4) and evaporated. The residue was purified by flash chromatography on silica gel with ethyl acetate:hexane (3:7). Selected spectral and analytical data for 2 (R2Y=PhTe; R1=n-Bu): 1H NMR (200 MHz, CDCl3): δ 7.92 (d, J=7.6 Hz, 2H), 7.42–7.21 (m, 3H), 6.27 (d, 2JP–H=16.4 Hz, 1H), 4.11 (dq, 3JP–H=7.5 Hz, J=7.2 Hz, 4H), 2.21 (t, J=7.8 Hz, 2H), 1.40–1.23 (m, 2H), 1.35 (t, J=7.2 Hz, 6H), 1.00 (sext, J=7.4 Hz, 2H), 0.66 (t, J=7 Hz, 3H); 13C NMR (50 MHz, CDCl3) δ 154.75 (d, 2JP–C=6.3 Hz), 141.43, 128.58, 128.27, 115.33 (d, 1JP–C=192 Hz), 115.29, 61.27 (d, 2JP–C=5 Hz), 41.67 (d, 3JP–C=23 Hz), 31.56, 21.16, 15.94 (d, 3JP–C=6.2 Hz), 13.05; 31P NMR (161 MHz, CDCl3) δ 15.33 (s); MS m/z (relative intensity) 426 (M+2, 25), 347 (15), 219 (76), 163 (80), 81 (100); IR (KBr, film; cm-1) 3064, 2956, 1559, 1433, 1391, 1292, 1231, 1163, 1027, 965. Anal. calcd for C16H25O3PTe: C, 45.33; H, 5.94. Found: C, 44.91; H, 5.80.