One-Pot Synthesis of Dihydropyrans via CO2 Reduction and Domino Knoevenagel/oxa-Diels-Alder Reactions

Kazuto Takaishi; Ritsuki Nishimura; Yuha Toda; Hajime Morishita; Tadashi Ema

doi:10.1021/acs.orglett.3c00047

One-Pot Synthesis of Dihydropyrans via CO₂ Reduction and Domino Knoevenagel/oxa-Diels-Alder Reactions

Kazuto Takaishi, Ritsuki Nishimura, Yuha Toda, Hajime Morishita, Tadashi Ema

Research output: Contribution to journal › Article › peer-review

Abstract

Catalytic CO₂ reduction with phenylsilane under solvent-free conditions was linked with the one-pot synthesis of 3,4-dihydropyrans from β-dicarbonyl compounds and styrenes. The synthesis includes three processes: (1) bis(silyl)acetal formation from CO₂ and phenylsilane and a domino reaction of (2) Knoevenagel condensation and (3) inverse-electron-demand oxa-Diels-Alder reaction. The first process was catalyzed by a pentanuclear Zn^II complex (0.07 mol %) to generate bis(silyl)acetals, which were hydrolyzed into formaldehyde to be used in the second step.

Original language	English
Journal	Organic Letters
DOIs	https://doi.org/10.1021/acs.orglett.3c00047
Publication status	Accepted/In press - 2023

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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@article{2176c4d5910142b6839f045c8bdacfe0,

title = "One-Pot Synthesis of Dihydropyrans via CO2 Reduction and Domino Knoevenagel/oxa-Diels-Alder Reactions",

abstract = "Catalytic CO2 reduction with phenylsilane under solvent-free conditions was linked with the one-pot synthesis of 3,4-dihydropyrans from β-dicarbonyl compounds and styrenes. The synthesis includes three processes: (1) bis(silyl)acetal formation from CO2 and phenylsilane and a domino reaction of (2) Knoevenagel condensation and (3) inverse-electron-demand oxa-Diels-Alder reaction. The first process was catalyzed by a pentanuclear ZnII complex (0.07 mol %) to generate bis(silyl)acetals, which were hydrolyzed into formaldehyde to be used in the second step.",

author = "Kazuto Takaishi and Ritsuki Nishimura and Yuha Toda and Hajime Morishita and Tadashi Ema",

note = "Funding Information: This work was supported by a Grant for Promotion of Science and Technology in Okayama Prefecture by MEXT and Nagase Science Technology Foundation. We thank Dr. Shigeki Mori (Ehime University) for the X-ray analyses. The computations were performed using RCCS, Okazaki, Japan (Project: 22-IMS-C115). Publisher Copyright: {\textcopyright} 2023 American Chemical Society.",

year = "2023",

doi = "10.1021/acs.orglett.3c00047",

language = "English",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

}

TY - JOUR

T1 - One-Pot Synthesis of Dihydropyrans via CO2 Reduction and Domino Knoevenagel/oxa-Diels-Alder Reactions

AU - Takaishi, Kazuto

AU - Nishimura, Ritsuki

AU - Toda, Yuha

AU - Morishita, Hajime

AU - Ema, Tadashi

N1 - Funding Information: This work was supported by a Grant for Promotion of Science and Technology in Okayama Prefecture by MEXT and Nagase Science Technology Foundation. We thank Dr. Shigeki Mori (Ehime University) for the X-ray analyses. The computations were performed using RCCS, Okazaki, Japan (Project: 22-IMS-C115). Publisher Copyright: © 2023 American Chemical Society.

PY - 2023

Y1 - 2023

N2 - Catalytic CO2 reduction with phenylsilane under solvent-free conditions was linked with the one-pot synthesis of 3,4-dihydropyrans from β-dicarbonyl compounds and styrenes. The synthesis includes three processes: (1) bis(silyl)acetal formation from CO2 and phenylsilane and a domino reaction of (2) Knoevenagel condensation and (3) inverse-electron-demand oxa-Diels-Alder reaction. The first process was catalyzed by a pentanuclear ZnII complex (0.07 mol %) to generate bis(silyl)acetals, which were hydrolyzed into formaldehyde to be used in the second step.

AB - Catalytic CO2 reduction with phenylsilane under solvent-free conditions was linked with the one-pot synthesis of 3,4-dihydropyrans from β-dicarbonyl compounds and styrenes. The synthesis includes three processes: (1) bis(silyl)acetal formation from CO2 and phenylsilane and a domino reaction of (2) Knoevenagel condensation and (3) inverse-electron-demand oxa-Diels-Alder reaction. The first process was catalyzed by a pentanuclear ZnII complex (0.07 mol %) to generate bis(silyl)acetals, which were hydrolyzed into formaldehyde to be used in the second step.

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U2 - 10.1021/acs.orglett.3c00047

DO - 10.1021/acs.orglett.3c00047

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JO - Organic Letters

JF - Organic Letters

ER -

One-Pot Synthesis of Dihydropyrans via CO₂ Reduction and Domino Knoevenagel/oxa-Diels-Alder Reactions

Abstract

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