Pt(II)-Chiral diene-catalyzed enantioselective formal [4 + 2] cycloaddition initiated by C–C bond cleavage and elucidation of a Pt(II)/(IV) cycle by DFT calculations

Takanori Shibata; Natsumi Shiozawa; Shun Nishibe; Hideaki Takano; Satoshi Maeda

doi:10.1039/D1QO01467F

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Pt(ii)-Chiral diene-catalyzed enantioselective formal [4 + 2] cycloaddition initiated by C–C bond cleavage and elucidation of a Pt(ii)/(iv) cycle by DFT calculations†

Takanori Shibata,

*^a Natsumi Shiozawa,^a Shun Nishibe,^a Hideaki Takano

^abc and Satoshi Maeda

*^bcd

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* Corresponding authors

^a Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Shinjuku, Tokyo 169-8555, Japan
E-mail: tshibata@waseda.jp

^b Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Kita 21 Nishi 10, Kita-ku, Sapporo, Hokkaido 001-0021, Japan
E-mail: smaeda@eis.hokudai.ac.jp

^c JST, ERATO Maeda Artificial Intelligence for Chemical Reaction Design and Discovery Project, Kita 10 Nishi 8, Kita-ku, Sapporo, Hokkaido 060-0810, Japan

^d Department of Chemistry, Faculty of Science, Hokkaido University, Kita 10 Nishi 8, Kita-ku, Sapporo, Hokkaido 060-0810, Japan

Abstract

A chiral Pt(II) complex was readily prepared from [PtCl₂(C₂H₄)]₂ and Hayashi's diene. Its dicationic derivative efficiently catalyzed a formal intramolecular [4 + 2] cycloaddition of biphenylenes possessing substituted arylalkynes tethered by an ortho-phenylene moiety at ambient temperature and axially chiral cycloadducts were obtained in excellent yields and ees. A study of the DFT calculations revealed a Pt(II)/(IV) cycle including oxidative addition of biphenylene along with C–C bond cleavage.

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DOI: https://doi.org/10.1039/D1QO01467F
Article type: Research Article
Submitted: 29 Sep 2021
Accepted: 26 Oct 2021
First published: 28 Oct 2021

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Org. Chem. Front., 2021,8, 6985-6991

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Pt(II)-Chiral diene-catalyzed enantioselective formal [4 + 2] cycloaddition initiated by C–C bond cleavage and elucidation of a Pt(II)/(IV) cycle by DFT calculations

T. Shibata, N. Shiozawa, S. Nishibe, H. Takano and S. Maeda, Org. Chem. Front., 2021, 8, 6985 DOI: 10.1039/D1QO01467F

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Organic Chemistry Frontiers

Pt(ii)-Chiral diene-catalyzed enantioselective formal [4 + 2] cycloaddition initiated by C–C bond cleavage and elucidation of a Pt(ii)/(iv) cycle by DFT calculations†

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Pt(II)-Chiral diene-catalyzed enantioselective formal [4 + 2] cycloaddition initiated by C–C bond cleavage and elucidation of a Pt(II)/(IV) cycle by DFT calculations

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