Fig. 5: Synthetic applications of iron-catalyzed alkylzincation of internal alkynes.
From: Iron-catalyzed alkyne alkylzincation affected by counterions
a High TON and gram scale experiment. b Synthesis of tetrasubstituted alkenes by carbozincation of internal alkyne. Reaction conditions: (i) D2O (150 μL), rt (~30 °C), 30 min; (ii) NCS (N-chlorosuccinimide, 3.0 equiv), THF, rt (~30 °C), 12 h; (iii) CuCN (20 mol%), allyl bromide (5.0 equiv), THF, rt (~30 °C), 4 h; (iv) methyl propiolate (3.0 equiv), CuCN (3.0 equiv), LiCl (3.0 equiv), THF, −70 °C, 12 h; (v) Pd(PPh3)4 (2 mol%), 4-iodonitrobenzene (0.5 equiv), THF, rt (~30 °C), 12 h; (vi) benzoyl chloride (3.0 equiv), CuCN (20 mol%), LiCl (3.0 equiv), THF, 0 °C, 12 h; (vii) 4-tolyl isocyanate (0.5 equiv), THF, rt (~30 °C), 12 h.
