American Chemical Society
ol2c02327_si_001.pdf (5.56 MB)

Iridium-Catalyzed Selective trans-Semihydrogenation of 1,3-Enynes with Ethanol: Access to (E,E)‑1,4-Diarylbutadienes

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journal contribution
posted on 2022-07-21, 14:10 authored by Fengjie Huang, Zhidao Huang, Guixia Liu, Zheng Huang
A trans-semihydrogenation of 1,3-enynes with ethanol as the hydrogen source was developed using a new (PCN)Ir complex as the precatalyst and tBuNH2 as the cocatalyst. This catalyst system provides an efficient and atom-economical access to unsymmetrical (E,E)-1,4-diarylbutadienes with high yields and stereoselectivities. Monitoring the process revealed that a sequence of cis-semihydrogenation of the triple bond of 1,3-enynes (to form (E,Z)-butadienes) and (E,Z)-to-(E,E) isomerization occurs to form (E,E)-butadienes.