Asymmetric domino heck arylation and alkylation of nonconjugated dienes : double C–F···sodium attractive noncovalent interaction

Asymmetric domino heck arylation and alkylation of nonconjugated dienes : double C–F···sodium attractive noncovalent interaction

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 sodiu...

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Main Authors: Zhu, Daoyong, Xu, Wenqiang, Pu, Maoping, Wu, Yun-Dong, Chi, Robin Yonggui, Zhou, Steve Jianrong
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2022
Subjects:
Science::Chemistry
Palladium
Hydrocarbons
Online Access:https://hdl.handle.net/10356/155069
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1550692022-02-22T08:35:27Z Asymmetric domino heck arylation and alkylation of nonconjugated dienes : double C–F···sodium attractive noncovalent interaction Zhu, Daoyong Xu, Wenqiang Pu, Maoping Wu, Yun-Dong Chi, Robin Yonggui Zhou, Steve Jianrong School of Physical and Mathematical Sciences Science::Chemistry Palladium Hydrocarbons 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. Economic Development Board (EDB) Nanyang Technological University We acknowledge financial support from Peking University Shenzhen Graduate School and Shenzhen Bay Laboratory for J.S.Z.; the National Natural Science Foundation of China (NSFC 21933004) for Y.-D.W.; Nanyang Technological University and GlaxoSmithKline and the Singapore Economic Development Board Trust Fund (2017 GSK-EDB Green & Sustainable Manufacturing Award) for Y.R.C. 2022-02-22T08:35:27Z 2022-02-22T08:35:27Z 2021 Journal Article Zhu, D., Xu, W., Pu, M., Wu, Y., Chi, R. Y. & Zhou, S. J. (2021). Asymmetric domino heck arylation and alkylation of nonconjugated dienes : double C–F···sodium attractive noncovalent interaction. Organic Letters, 23(18), 7064-7068. https://dx.doi.org/10.1021/acs.orglett.1c02457 1523-7060 https://hdl.handle.net/10356/155069 10.1021/acs.orglett.1c02457 34469162 2-s2.0-85114858204 18 23 7064 7068 en Organic Letters © 2021 American Chemical Society. All rights reserved.
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Science::Chemistry
Palladium
Hydrocarbons
spellingShingle Science::Chemistry
Palladium
Hydrocarbons
Zhu, Daoyong
Xu, Wenqiang
Pu, Maoping
Wu, Yun-Dong
Chi, Robin Yonggui
Zhou, Steve Jianrong
Asymmetric domino heck arylation and alkylation of nonconjugated dienes : double C–F···sodium attractive noncovalent interaction
description 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.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Zhu, Daoyong
Xu, Wenqiang
Pu, Maoping
Wu, Yun-Dong
Chi, Robin Yonggui
Zhou, Steve Jianrong
format Article
author Zhu, Daoyong
Xu, Wenqiang
Pu, Maoping
Wu, Yun-Dong
Chi, Robin Yonggui
Zhou, Steve Jianrong
author_sort Zhu, Daoyong
title Asymmetric domino heck arylation and alkylation of nonconjugated dienes : double C–F···sodium attractive noncovalent interaction
title_short Asymmetric domino heck arylation and alkylation of nonconjugated dienes : double C–F···sodium attractive noncovalent interaction
title_full Asymmetric domino heck arylation and alkylation of nonconjugated dienes : double C–F···sodium attractive noncovalent interaction
title_fullStr Asymmetric domino heck arylation and alkylation of nonconjugated dienes : double C–F···sodium attractive noncovalent interaction
title_full_unstemmed Asymmetric domino heck arylation and alkylation of nonconjugated dienes : double C–F···sodium attractive noncovalent interaction
title_sort asymmetric domino heck arylation and alkylation of nonconjugated dienes : double c–f···sodium attractive noncovalent interaction
publishDate 2022
url https://hdl.handle.net/10356/155069
_version_ 1725985675064377344

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