Asymmetric Domino Heck Arylation and Alkylation of Nonconjugated Dienes: Double C-F···Sodium Attractive Noncovalent Interaction

Daoyong Zhu; Wenqiang Xu; Maoping Pu; Yun Dong Wu; Yonggui Robin Chi; Jianrong Steve Zhou

doi:10.1021/acs.orglett.1c02457

Asymmetric Domino Heck Arylation and Alkylation of Nonconjugated Dienes: Double C-F···Sodium Attractive Noncovalent Interaction

Daoyong Zhu, Wenqiang Xu, Maoping Pu, Yun Dong Wu, Yonggui Robin Chi, Jianrong Steve Zhou^*

^*Corresponding author for this work

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

9 Citations (Scopus)

Abstract

Palladium catalyzes a domino Heck arylation and alkylation of nonconjugated cyclodienes to produce trans isomers of disubstituted cyclohexenes in exceptionally high enantiomeric ratios, reaching 100:1 to 200:1 in many cases. Importantly, the interactions of the two CF bonds of Josiphos and the sodium ion of malonates facilitates stereoselective allylic attack through DFT calculations and experiments. This is a new type of attractive noncovalent interactions found in organometallic catalysis.

Original language	English
Pages (from-to)	7064-7068
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	18
DOIs	https://doi.org/10.1021/acs.orglett.1c02457
Publication status	Published - Sept 17 2021
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2021 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Asymmetric Domino Heck Arylation and Alkylation of Nonconjugated Dienes: Double C-F···Sodium Attractive Noncovalent Interaction",

abstract = "Palladium catalyzes a domino Heck arylation and alkylation of nonconjugated cyclodienes to produce trans isomers of disubstituted cyclohexenes in exceptionally high enantiomeric ratios, reaching 100:1 to 200:1 in many cases. Importantly, the interactions of the two CF bonds of Josiphos and the sodium ion of malonates facilitates stereoselective allylic attack through DFT calculations and experiments. This is a new type of attractive noncovalent interactions found in organometallic catalysis.",

author = "Daoyong Zhu and Wenqiang Xu and Maoping Pu and Wu, {Yun Dong} and Chi, {Yonggui Robin} and Zhou, {Jianrong Steve}",

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T1 - Asymmetric Domino Heck Arylation and Alkylation of Nonconjugated Dienes

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AU - Zhu, Daoyong

AU - Xu, Wenqiang

AU - Pu, Maoping

AU - Wu, Yun Dong

AU - Chi, Yonggui Robin

AU - Zhou, Jianrong Steve

PY - 2021/9/17

Y1 - 2021/9/17

N2 - Palladium catalyzes a domino Heck arylation and alkylation of nonconjugated cyclodienes to produce trans isomers of disubstituted cyclohexenes in exceptionally high enantiomeric ratios, reaching 100:1 to 200:1 in many cases. Importantly, the interactions of the two CF bonds of Josiphos and the sodium ion of malonates facilitates stereoselective allylic attack through DFT calculations and experiments. This is a new type of attractive noncovalent interactions found in organometallic catalysis.

AB - Palladium catalyzes a domino Heck arylation and alkylation of nonconjugated cyclodienes to produce trans isomers of disubstituted cyclohexenes in exceptionally high enantiomeric ratios, reaching 100:1 to 200:1 in many cases. Importantly, the interactions of the two CF bonds of Josiphos and the sodium ion of malonates facilitates stereoselective allylic attack through DFT calculations and experiments. This is a new type of attractive noncovalent interactions found in organometallic catalysis.

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JO - Organic Letters

JF - Organic Letters

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Asymmetric Domino Heck Arylation and Alkylation of Nonconjugated Dienes: Double C-F···Sodium Attractive Noncovalent Interaction

Abstract

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ASJC Scopus Subject Areas

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