Highly Efficient and Eco-friendly Gold Catalysed Synthesis of Homoallylic Ketones

Danila Gasperini; Adrian Goméz-Suàrez; Sai V. M. Vummaleti; Albert Poater; Luigi  Cavallo; Steven P. Nolan

doi:10.1021/cs500806m

Highly Efficient and Eco-friendly Gold Catalysed Synthesis of Homoallylic Ketones

Danila Gasperini, Adrian Goméz-Suàrez, Sai V. M. Vummaleti, Albert Poater, Luigi Cavallo, Steven P. Nolan

Department of Chemistry

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

57 Citations (SciVal)

Abstract

We report a new catalytic protocol for the synthesis of γ,δ−unsaturated carbonyl units from simple starting materials, allylic alcohols and alkynes, via a hydroxalkoxylation/Claisen rearrangement sequence. This new process is more efficient (higher TON and TOF) and more eco-friendly (increased mass efficiency) than the previous state-of-the-art technique. In addition, this method tolerates both terminal and internal alkynes. Moreover, computational studies have been carried out in order to shed light on how the Claisen rearrangement is initiated.

Original language	English
Pages (from-to)	2701-2705
Number of pages	5
Journal	ACS Catalysis
Volume	4
Issue number	8
DOIs	https://doi.org/10.1021/cs500806m
Publication status	Published - 15 Jul 2014

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abstract = "We report a new catalytic protocol for the synthesis of γ,δ−unsaturated carbonyl units from simple starting materials, allylic alcohols and alkynes, via a hydroxalkoxylation/Claisen rearrangement sequence. This new process is more efficient (higher TON and TOF) and more eco-friendly (increased mass efficiency) than the previous state-of-the-art technique. In addition, this method tolerates both terminal and internal alkynes. Moreover, computational studies have been carried out in order to shed light on how the Claisen rearrangement is initiated.",

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AU - Gasperini, Danila

AU - Goméz-Suàrez, Adrian

AU - Vummaleti, Sai V. M.

AU - Poater, Albert

AU - Cavallo, Luigi

AU - Nolan, Steven P.

PY - 2014/7/15

Y1 - 2014/7/15

N2 - We report a new catalytic protocol for the synthesis of γ,δ−unsaturated carbonyl units from simple starting materials, allylic alcohols and alkynes, via a hydroxalkoxylation/Claisen rearrangement sequence. This new process is more efficient (higher TON and TOF) and more eco-friendly (increased mass efficiency) than the previous state-of-the-art technique. In addition, this method tolerates both terminal and internal alkynes. Moreover, computational studies have been carried out in order to shed light on how the Claisen rearrangement is initiated.

AB - We report a new catalytic protocol for the synthesis of γ,δ−unsaturated carbonyl units from simple starting materials, allylic alcohols and alkynes, via a hydroxalkoxylation/Claisen rearrangement sequence. This new process is more efficient (higher TON and TOF) and more eco-friendly (increased mass efficiency) than the previous state-of-the-art technique. In addition, this method tolerates both terminal and internal alkynes. Moreover, computational studies have been carried out in order to shed light on how the Claisen rearrangement is initiated.

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DO - 10.1021/cs500806m

M3 - Article

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JF - ACS Catalysis

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Highly Efficient and Eco-friendly Gold Catalysed Synthesis of Homoallylic Ketones

Abstract

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