Palladium-catalysed mono-α-alkenylation of ketones with alkenyl tosylates

Yong Wu; Wai Chung Fu; Chien Wei Chiang; Pui Ying Choy; Fuk Yee Kwong; Aiwen Lei

doi:10.1039/c6cc08392g

Palladium-catalysed mono-α-alkenylation of ketones with alkenyl tosylates

Yong Wu, Wai Chung Fu, Chien Wei Chiang, Pui Ying Choy, Fuk Yee Kwong, Aiwen Lei

The Hong Kong Polytechnic University

Research output: Journal article publication › Journal article › Academic research › peer-review

17 Citations (Scopus)

Abstract

The first example of palladium-catalysed selective mono-α-alkenylation of ketones with alkenyl tosylates is described. In the presence of a Pd/XPhos catalyst system (0.1-1.0 mol%), the reaction provides mono-α-alkenylated ketones in good yields and exhibits excellent substrate tolerance. Highly congested, tri- and tetra-substituted alkenyl tosylates react smoothly and even problematic heteroaryl and aliphatic ketones are applicable substrates. Notably, small β,γ-unsaturated ketones are successfully prepared using acetone as a simple three-carbon feedstock.

Original language	English
Pages (from-to)	952-955
Number of pages	4
Journal	Chemical Communications
Volume	53
Issue number	5
DOIs	https://doi.org/10.1039/c6cc08392g
Publication status	Published - 2017

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/c6cc08392g

http://hdl.handle.net/10397/101600

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title = "Palladium-catalysed mono-α-alkenylation of ketones with alkenyl tosylates",

abstract = "The first example of palladium-catalysed selective mono-α-alkenylation of ketones with alkenyl tosylates is described. In the presence of a Pd/XPhos catalyst system (0.1-1.0 mol%), the reaction provides mono-α-alkenylated ketones in good yields and exhibits excellent substrate tolerance. Highly congested, tri- and tetra-substituted alkenyl tosylates react smoothly and even problematic heteroaryl and aliphatic ketones are applicable substrates. Notably, small β,γ-unsaturated ketones are successfully prepared using acetone as a simple three-carbon feedstock.",

author = "Yong Wu and Fu, {Wai Chung} and Chiang, {Chien Wei} and Choy, {Pui Ying} and Kwong, {Fuk Yee} and Aiwen Lei",

note = "Funding Information: This work was supported by the National Natural Science Foundation of China (21390402, 21520102003), the Ministry of Science and Technology of China (2012YQ120060), the Fundamental Research Funds for the Central Universities and the Program of Introducing Talents of Discipline to Universities of China (111 Program). We also thank the Research Grants Council of Hong Kong (CRF: C5023-14G), General Research Fund (PolyU 153034/15P), and State Key Laboratory of Chirosciences for financial support. This work was supported by the Joint Supervision Scheme of The Hong Kong Polytechnic University. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",

year = "2017",

doi = "10.1039/c6cc08392g",

language = "English",

volume = "53",

pages = "952--955",

journal = "Chemical Communications",

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T1 - Palladium-catalysed mono-α-alkenylation of ketones with alkenyl tosylates

AU - Wu, Yong

AU - Fu, Wai Chung

AU - Chiang, Chien Wei

AU - Choy, Pui Ying

AU - Kwong, Fuk Yee

AU - Lei, Aiwen

N1 - Funding Information: This work was supported by the National Natural Science Foundation of China (21390402, 21520102003), the Ministry of Science and Technology of China (2012YQ120060), the Fundamental Research Funds for the Central Universities and the Program of Introducing Talents of Discipline to Universities of China (111 Program). We also thank the Research Grants Council of Hong Kong (CRF: C5023-14G), General Research Fund (PolyU 153034/15P), and State Key Laboratory of Chirosciences for financial support. This work was supported by the Joint Supervision Scheme of The Hong Kong Polytechnic University. Publisher Copyright: © The Royal Society of Chemistry.

PY - 2017

Y1 - 2017

N2 - The first example of palladium-catalysed selective mono-α-alkenylation of ketones with alkenyl tosylates is described. In the presence of a Pd/XPhos catalyst system (0.1-1.0 mol%), the reaction provides mono-α-alkenylated ketones in good yields and exhibits excellent substrate tolerance. Highly congested, tri- and tetra-substituted alkenyl tosylates react smoothly and even problematic heteroaryl and aliphatic ketones are applicable substrates. Notably, small β,γ-unsaturated ketones are successfully prepared using acetone as a simple three-carbon feedstock.

AB - The first example of palladium-catalysed selective mono-α-alkenylation of ketones with alkenyl tosylates is described. In the presence of a Pd/XPhos catalyst system (0.1-1.0 mol%), the reaction provides mono-α-alkenylated ketones in good yields and exhibits excellent substrate tolerance. Highly congested, tri- and tetra-substituted alkenyl tosylates react smoothly and even problematic heteroaryl and aliphatic ketones are applicable substrates. Notably, small β,γ-unsaturated ketones are successfully prepared using acetone as a simple three-carbon feedstock.

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U2 - 10.1039/c6cc08392g

DO - 10.1039/c6cc08392g

M3 - Journal article

C2 - 28044153

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SN - 1359-7345

VL - 53

SP - 952

EP - 955

JO - Chemical Communications

JF - Chemical Communications

IS - 5

ER -

Palladium-catalysed mono-α-alkenylation of ketones with alkenyl tosylates

Abstract

ASJC Scopus subject areas

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