Para-Selective C-H Olefination of Aniline Derivatives via Pd/S,O-Ligand Catalysis

Kananat Naksomboon; Jordi Poater; F. Matthias Bickelhaupt; M. Ángeles Fernández-Ibáñez

doi:10.1021/jacs.9b01908

Para-Selective C-H Olefination of Aniline Derivatives via Pd/S,O-Ligand Catalysis

Kananat Naksomboon
, Jordi Poater
, F. Matthias Bickelhaupt
, M. Ángeles Fernández-Ibáñez^*

^*Corresponding author for this work

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Research output: Contribution to Journal › Article › Academic › peer-review

Abstract

Herein we report a highly para-selective C-H olefination of aniline derivatives by a Pd/S,O-ligand-based catalyst. The reaction proceeds under mild reaction conditions with high efficiency and broad substrate scope, including mono-, di-, and trisubstituted tertiary, secondary, and primary anilines. The S,O-ligand is responsible for the dramatic improvements in substrate scope and the high para-selectivity observed. This methodology is operationally simple, scalable, and can be performed under aerobic conditions.

Original language	English
Pages (from-to)	6719-6725
Number of pages	7
Journal	Journal of the American Chemical Society
Volume	141
Issue number	16
Early online date	28 Mar 2019
DOIs	https://doi.org/10.1021/jacs.9b01908
Publication status	Published - 24 Apr 2019

Funding

We acknowledge financial support from NWO through a VIDI grant (723.013.006). J.P. thanks the Spanish MINECO (CTQ2016-77558-R and MDM-2017-0767). We thank Nick Westerveld for the synthesis of some protected aniline derivatives and Nippon Inorganic Colour & Chemical Co., Ltd. for providing us H6PMo9V3O40·30H2O.

Funders	Funder number
NWO	723.013.006

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This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1021/jacs.9b01908

https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6487392

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title = "Para-Selective C-H Olefination of Aniline Derivatives via Pd/S,O-Ligand Catalysis",

abstract = "Herein we report a highly para-selective C-H olefination of aniline derivatives by a Pd/S,O-ligand-based catalyst. The reaction proceeds under mild reaction conditions with high efficiency and broad substrate scope, including mono-, di-, and trisubstituted tertiary, secondary, and primary anilines. The S,O-ligand is responsible for the dramatic improvements in substrate scope and the high para-selectivity observed. This methodology is operationally simple, scalable, and can be performed under aerobic conditions.",

author = "Kananat Naksomboon and Jordi Poater and Bickelhaupt, \{F. Matthias\} and Fern{\'a}ndez-Ib{\'a}{\~n}ez, \{M. {\'A}ngeles\}",

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AU - Naksomboon, Kananat

AU - Poater, Jordi

AU - Bickelhaupt, F. Matthias

AU - Fernández-Ibáñez, M. Ángeles

PY - 2019/4/24

Y1 - 2019/4/24

N2 - Herein we report a highly para-selective C-H olefination of aniline derivatives by a Pd/S,O-ligand-based catalyst. The reaction proceeds under mild reaction conditions with high efficiency and broad substrate scope, including mono-, di-, and trisubstituted tertiary, secondary, and primary anilines. The S,O-ligand is responsible for the dramatic improvements in substrate scope and the high para-selectivity observed. This methodology is operationally simple, scalable, and can be performed under aerobic conditions.

AB - Herein we report a highly para-selective C-H olefination of aniline derivatives by a Pd/S,O-ligand-based catalyst. The reaction proceeds under mild reaction conditions with high efficiency and broad substrate scope, including mono-, di-, and trisubstituted tertiary, secondary, and primary anilines. The S,O-ligand is responsible for the dramatic improvements in substrate scope and the high para-selectivity observed. This methodology is operationally simple, scalable, and can be performed under aerobic conditions.

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 16

ER -

Para-Selective C-H Olefination of Aniline Derivatives via Pd/S,O-Ligand Catalysis

Abstract

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