. 2014 Oct 20;136(43):15403–15413. doi: 10.1021/ja508632y

Table 5. Optimization of Chemoselective Barbier-Type Reaction^a.

graphic file with name ja-2014-08632y_0013.jpg

graphic file with name ja-2014-08632y_0014.jpg

Reagents and conditions: (a) i. propyne (1.0 equiv), Co(CO)₈ (1.0 equiv), CH₂Cl₂, rt, 2 h; ii. 40 (3.0 equiv), NMO (6.0 equiv), ethylene glycol/CH₂Cl₂ (1:10, 0.1M) rt, 12 h. (b) CeCl₃ (1.0 equiv), NaBH₄ (4.0 equiv), MeOH, 0 °C, 12 h. (c) PPh₃ (3.4 equiv), NCS (3.4 equiv), THF, rt, 12 h. (d) propionaldehyde (4.0 equiv), Zn (16.0 equiv), In (2 equiv), THF/6% NH₄Cl (aq), rt, 3 h.

Table 5. Optimization of Chemoselective Barbier-Type Reactiona.

Table 5. Optimization of Chemoselective Barbier-Type Reaction^a.