pyridine; pyridine hydrogenfluoride in acetonitrile 4 h; Ambient temperature;

<b>Multi-step reaction with 4 steps<br /> </b>1: 1.) (c-C₆H₁₁)2BH, 2.) aq. NaOH / 2.) Pd(PPh₃)4 / 1.) THF, r.t., 1 h, 2.) benzene, 65 deg C, 1 h<br />2: 70percent m-CPBA / CH₂Cl₂ / 1 h / Ambient temperature<br />3: BF₃*Et₂O, MeOH / 0.5 h / 0 &deg;C<br />4: 1.) t-BuLi, 2-thienyl(cyano)copper lithium / 1.) pentane, Et₂O, -78 deg C, 30 min; THF, -78 deg C, 30 min, 2.) -78 deg C, 1 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 79 percent / mesyl chloride, triethylamine / CH₂Cl₂ / 1 h / 0 &deg;C<br />2: 1) t-BuLi; 2) CuI, Bu₃P; 5) 25percent aq. TiCl₃, NH₄OAc<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 51 percent / sodium nitrite, phloroglucinol / dimethylsulfoxide / 20 h / Ambient temperature<br />2: 1) 3N sodium hydroxide; 3) acetic acid / 1) H₂O, 0 deg C, 3 h; 2) H₂O, 0 deg C, 5 h; 3) H₂O, room temp., 20 h<br />3: 79 percent / mesyl chloride, triethylamine / CH₂Cl₂ / 1 h / 0 &deg;C<br />4: 1) t-BuLi; 2) CuI, Bu₃P; 5) 25percent aq. TiCl₃, NH₄OAc<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 1) 3N sodium hydroxide; 3) acetic acid / 1) H₂O, 0 deg C, 3 h; 2) H₂O, 0 deg C, 5 h; 3) H₂O, room temp., 20 h<br />2: 79 percent / mesyl chloride, triethylamine / CH₂Cl₂ / 1 h / 0 &deg;C<br />3: 1) t-BuLi; 2) CuI, Bu₃P; 5) 25percent aq. TiCl₃, NH₄OAc<br /> <br /> &nbsp;