Fig. 5: Synthetic applications of 4a. | Nature Communications

Fig. 5: Synthetic applications of 4a.

From: Ni-catalyzed regio- and stereo-defined intermolecular cross-electrophile dialkylation of alkynes without directing group

Fig. 5

Reaction conditions: a Reductive amination. (1) PhNH2, MgSO4, AcOH, DCM (0.2 M), rt, 2 h; (2) NaBH3CN, MeOH, rt, 10 h. b Reduction. NaBH4, MeOH, rt, 2 h. c Wittig Olefination. n-BuLi, Ph3PCH2Br, THF, −30 °C to rt, overnight. d Epoxidation. m-CPBA, NaHCO3, DCM, 0 °C, 2 h. e Desaturation. Pd(TFA)2, 1 atm O2, DMSO, 85 °C, 14 h. f Aromatization. Pd(TFA)2, PTSA, N,N-dimethylpyridin-2-amine, 1 atm O2, DMSO, 80 °C, 24 h.

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