Reductive Coupling of Acrylates with Ketones and Ketimines by a Nickel-Catalyzed Transfer-Hydrogenative Strategy

Craig Buxton; David C. Blakemore; John Bower

doi:10.1002/anie.201707531

Reductive Coupling of Acrylates with Ketones and Ketimines by a Nickel-Catalyzed Transfer-Hydrogenative Strategy

Craig Buxton, David C. Blakemore, John Bower

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

26 Citations (Scopus)

278 Downloads (Pure)

Abstract

Nickel-catalyzed coupling of benzyl acrylates with activated ketones and imines provides γ-butyrolactones and lactams, respectively. The benzyl alcohol byproduct released during the lactonization/lactamization event is relayed to the next cycle where it serves as the reductant for C−C bond formation. This strategy represents a conceptually unique approach to transfer-hydrogenative C−C bond formation, thus providing examples of reductive heterocyclizations where hydrogen embedded within an alcohol leaving group facilitates turnover.

Original language	English
Pages (from-to)	13824-13828
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	44
Early online date	4 Sept 2017
DOIs	https://doi.org/10.1002/anie.201707531
Publication status	Published - 23 Oct 2017

Research Groups and Themes

BCS and TECS CDTs

Keywords

alcohols
lactones
nickel
spiro compounds
transfer hydrogenation

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10.1002/anie.201707531

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A 13C NMR Coldprobe to Underpin Chemistry Research.
Butts, C. P. (Principal Investigator)
28/02/14 → 29/11/17
Project: Research
3-month Core Capability for Chemistry Research
Crosby, J. (Principal Investigator)
1/01/13 → 1/04/13
Project: Research

Cite this

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title = "Reductive Coupling of Acrylates with Ketones and Ketimines by a Nickel-Catalyzed Transfer-Hydrogenative Strategy",

abstract = "Nickel-catalyzed coupling of benzyl acrylates with activated ketones and imines provides γ-butyrolactones and lactams, respectively. The benzyl alcohol byproduct released during the lactonization/lactamization event is relayed to the next cycle where it serves as the reductant for C−C bond formation. This strategy represents a conceptually unique approach to transfer-hydrogenative C−C bond formation, thus providing examples of reductive heterocyclizations where hydrogen embedded within an alcohol leaving group facilitates turnover.",

keywords = "alcohols, lactones, nickel, spiro compounds, transfer hydrogenation",

author = "Craig Buxton and Blakemore, {David C.} and John Bower",

year = "2017",

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doi = "10.1002/anie.201707531",

language = "English",

volume = "56",

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journal = "Angewandte Chemie - International Edition",

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publisher = "Wiley-VCH Verlag",

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TY - JOUR

T1 - Reductive Coupling of Acrylates with Ketones and Ketimines by a Nickel-Catalyzed Transfer-Hydrogenative Strategy

AU - Buxton, Craig

AU - Blakemore, David C.

AU - Bower, John

PY - 2017/10/23

Y1 - 2017/10/23

N2 - Nickel-catalyzed coupling of benzyl acrylates with activated ketones and imines provides γ-butyrolactones and lactams, respectively. The benzyl alcohol byproduct released during the lactonization/lactamization event is relayed to the next cycle where it serves as the reductant for C−C bond formation. This strategy represents a conceptually unique approach to transfer-hydrogenative C−C bond formation, thus providing examples of reductive heterocyclizations where hydrogen embedded within an alcohol leaving group facilitates turnover.

AB - Nickel-catalyzed coupling of benzyl acrylates with activated ketones and imines provides γ-butyrolactones and lactams, respectively. The benzyl alcohol byproduct released during the lactonization/lactamization event is relayed to the next cycle where it serves as the reductant for C−C bond formation. This strategy represents a conceptually unique approach to transfer-hydrogenative C−C bond formation, thus providing examples of reductive heterocyclizations where hydrogen embedded within an alcohol leaving group facilitates turnover.

KW - alcohols

KW - lactones

KW - nickel

KW - spiro compounds

KW - transfer hydrogenation

U2 - 10.1002/anie.201707531

DO - 10.1002/anie.201707531

M3 - Article (Academic Journal)

C2 - 28868751

SN - 1433-7851

VL - 56

SP - 13824

EP - 13828

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 44

ER -

Reductive Coupling of Acrylates with Ketones and Ketimines by a Nickel-Catalyzed Transfer-Hydrogenative Strategy

Abstract

Research Groups and Themes

Keywords

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A 13C NMR Coldprobe to Underpin Chemistry Research.

3-month Core Capability for Chemistry Research

Cite this