Fig. 5: Downstream applications and transformations. | Nature Communications

Fig. 5: Downstream applications and transformations.

From: Chemo-, regio- and stereoselective access to polysubstituted 1,3-dienes via Nickel-catalyzed four-component reactions

Fig. 5

a convert the reactive C-I bond derived from aryl boroxines. b transform the ester groups originated from accessible terminal alkynes. Reaction condition: a45 (0.05 mmol), 3-ethynylanisole (3.0 equiv), PdCl2(PPh3)2 (10 mol%), CuI (5 mol%) in Et3N and THF at rt for 12 h. b45 (0.05 mmol), methyl acrylate (5.0 equiv), Pd(tBu3P)2 (10 mol%), and N, N-dicyclohexylmethylamine (2.0 equiv) in THF at 50 oC for 12 h. c45 (0.05 mmol), (4-Ethoxycarbonylphenyl)boronic acid (1.5 equiv), Pd(PPh3)2Cl2 (10 mol%), Na2CO3 (2.0 equiv) in THF and H2O at 80 oC for 12 h. d45 (0.05 mmol), Pd(OAc)2 (5 mol%), Xantphos (10 mol%), Cs2CO3 (4.0 equiv) in 1,4-dioxane at 100 oC for 12 h. e45 (0.05 mmol), DIBAL-H (10 equiv) in THF at −78 oC for 6 h. f70 (0.05 mmol), PCC (2.4 equiv) in DCM at rt for 4 h. g71 (0.05 mmol), MePPh3Br (3.0 equiv), K2CO3 (4.0 equiv) in 1,4-dioxane at 80 oC for 12 h. h45 (0.05 mmol), NaOH (20 equiv) in MeOH and THF at 80 oC for 8 h. DIBAL-H = diisobutylaluminium hydride, PCC = pyridinium chlorochromate.

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