Palladium-Catalyzed Semihydrogenation of Alkynes with EtOH: Highly Stereoselective Synthesis of E- and Z-Alkenes

Chengniu Wang; Jin Dong; Tingting Li; Xi Zhao; Dawei Xu

doi:10.1055/a-1736-8721

Synthesis, Table of Contents

Synthesis 2022; 54(11): 2687-2695
DOI: 10.1055/a-1736-8721

paper

Palladium-Catalyzed Semihydrogenation of Alkynes with EtOH: Highly Stereoselective Synthesis of E- and Z-Alkenes

Chengniu Wang∗

^aMedical School, Institute of Reproductive Medicine, Nantong University, Nantong 226001, Jiangsu, P. R. of China

,

Jin Dong‡

^aMedical School, Institute of Reproductive Medicine, Nantong University, Nantong 226001, Jiangsu, P. R. of China

,

Tingting Li

^aMedical School, Institute of Reproductive Medicine, Nantong University, Nantong 226001, Jiangsu, P. R. of China

,

Xi Zhao

^aMedical School, Institute of Reproductive Medicine, Nantong University, Nantong 226001, Jiangsu, P. R. of China

,

Dawei Xu∗

^bDepartment of Orthopaedics, Affiliated Hospital 2 of Nantong University, Nantong 226001, Jiangsu, P. R. of China

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Abstract

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Abstract

A palladium-catalyzed semihydrogenation of alkynes to E- and Z-alkenes employing EtOH as the hydrogenating agent is reported. The selectivity of the reaction system was effectively controlled by ligand/additive and solvent regulation. The use of sodium acetate/triethanolamine (NaOAc/TEOA), THF, and (1R,2R)-bis[(2-methoxyphenyl)phenylphosphino]ethane [(R,R)-DIPAMP] in CH₃CN was critical for the stereoselective semihydrogenation of alkynes. The general applicability of this procedure was highlighted by the synthesis of more than 36 alkenes, in good yields with high stereoselectivities.

Keywords

semihydrogenation - alkynes - palladium-catalyzed - highly stereoselective - EtOH as a hydrogen source

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References

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