Systematic Study on the Catalytic Arsa-Wittig Reaction

Ryoto Inaba; Ikuo Kawashima; Toshiki Fujii; Takashi Yumura; Hiroaki Imoto; Kensuke Naka

doi:10.1002/chem.202002792

Systematic Study on the Catalytic Arsa-Wittig Reaction

Chemistry. 2020 Oct 21;26(59):13400-13407. doi: 10.1002/chem.202002792. Epub 2020 Sep 16.

Authors

Ryoto Inaba¹, Ikuo Kawashima¹, Toshiki Fujii¹, Takashi Yumura², Hiroaki Imoto^{1

3}, Kensuke Naka^{1

3}

Affiliations

¹ Faculty of Molecular Chemistry and Engineering, Graduate School of, Science and Technology, Kyoto Institute of Technology, Goshokaido-cho, Matsugasaki, Sakyo-ku, Kyoto, 6068585, Japan.
² Faculty of Material Science and Technology, Graduate School of, Science and Technology, Kyoto Institute of Technology, Goshokaido-cho, Matsugasaki, Sakyo-ku, Kyoto, 606-8585, Japan.
³ Materials Innovation Lab, Kyoto Institute of Technology, Goshokaido-cho, Matsugasaki, Sakyo-ku, Kyoto, 6068585, Japan.

PMID: 32662545
DOI: 10.1002/chem.202002792

Abstract

Efficient catalytic arsa-Wittig reactions have been developed by using 1-phenylarsolane as a catalyst. A wide array of aldehydes was converted to the corresponding olefins in high yields with moderate to excellent E stereoselectivity in the presence of a catalytic amount of 1-phenylarsolane. Moreover, density functional theory calculations were carried out to afford insight into the E/Z selectivity.

Keywords: E/Z selectivity; arsenic; catalytic arsa-Wittig reaction; density functional calculations; iron-free.