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C‐C Bond Formation by Dual Pyrrolidine and Nickel Catalysis: Allylation of Ketones by Allylic Alcohols

Research output: Contribution to Journal/Magazine › Journal article › peer-review

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C‐C Bond Formation by Dual Pyrrolidine and Nickel Catalysis: Allylation of Ketones by Allylic Alcohols. / Wright, Noah; Townsend, Bara; Nicholson, Steven et al.
In: Advanced Synthesis & Catalysis, Vol. 366, No. 18, 17.09.2024, p. 3833-3838.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Wright, N, Townsend, B, Nicholson, S, Robinson, J, Akien, G, Ball, AK, Sweeney, JB & Doulcet, J 2024, 'C‐C Bond Formation by Dual Pyrrolidine and Nickel Catalysis: Allylation of Ketones by Allylic Alcohols', Advanced Synthesis & Catalysis, vol. 366, no. 18, pp. 3833-3838. https://doi.org/10.1002/adsc.202400610

APA

Wright, N., Townsend, B., Nicholson, S., Robinson, J., Akien, G., Ball, A. K., Sweeney, J. B., & Doulcet, J. (2024). C‐C Bond Formation by Dual Pyrrolidine and Nickel Catalysis: Allylation of Ketones by Allylic Alcohols. Advanced Synthesis & Catalysis, 366(18), 3833-3838. https://doi.org/10.1002/adsc.202400610

Vancouver

Wright N, Townsend B, Nicholson S, Robinson J, Akien G, Ball AK et al. C‐C Bond Formation by Dual Pyrrolidine and Nickel Catalysis: Allylation of Ketones by Allylic Alcohols. Advanced Synthesis & Catalysis. 2024 Sept 17;366(18):3833-3838. Epub 2024 Sept 12. doi: 10.1002/adsc.202400610

Author

Wright, Noah ; Townsend, Bara ; Nicholson, Steven et al. / C‐C Bond Formation by Dual Pyrrolidine and Nickel Catalysis : Allylation of Ketones by Allylic Alcohols. In: Advanced Synthesis & Catalysis. 2024 ; Vol. 366, No. 18. pp. 3833-3838.

Bibtex

@article{e4c8b683dac747bcb61bffbb40924ce7,
title = "C‐C Bond Formation by Dual Pyrrolidine and Nickel Catalysis: Allylation of Ketones by Allylic Alcohols",
abstract = "Whilst catalytic ketone allylation using palladium(0) is well–precedented, nickel(0)‐catalysed equivalents of such reactions remain scarce. We report here the first nickel‐catalysed allylation of ketones which uses an easily handled and inexpensive bench‐stable Ni(II) pre‐catalyst. This method avoids generation of stoichiometric by‐products via the use of readily available allyl alcohols, rather than the esters or related derivatives which are often used in such transformations. Under the optimised conditions, 25 monoallylated ketones were obtained in 16% to 98% yield and with high selectivity for the linear (E)–isomers.",
keywords = "Allylation, C−C coupling, Ketone, Nickel, Sustainable catalysis",
author = "Noah Wright and Bara Townsend and Steven Nicholson and Joshua Robinson and Geoffrey Akien and Ball, {Anthony K.} and Sweeney, {Joseph B.} and Julien Doulcet",
year = "2024",
month = sep,
day = "17",
doi = "10.1002/adsc.202400610",
language = "English",
volume = "366",
pages = "3833--3838",
journal = "Advanced Synthesis & Catalysis",
issn = "1615-4150",
publisher = "Wiley",
number = "18",

}

RIS

TY - JOUR

T1 - C‐C Bond Formation by Dual Pyrrolidine and Nickel Catalysis

T2 - Allylation of Ketones by Allylic Alcohols

AU - Wright, Noah

AU - Townsend, Bara

AU - Nicholson, Steven

AU - Robinson, Joshua

AU - Akien, Geoffrey

AU - Ball, Anthony K.

AU - Sweeney, Joseph B.

AU - Doulcet, Julien

PY - 2024/9/17

Y1 - 2024/9/17

N2 - Whilst catalytic ketone allylation using palladium(0) is well–precedented, nickel(0)‐catalysed equivalents of such reactions remain scarce. We report here the first nickel‐catalysed allylation of ketones which uses an easily handled and inexpensive bench‐stable Ni(II) pre‐catalyst. This method avoids generation of stoichiometric by‐products via the use of readily available allyl alcohols, rather than the esters or related derivatives which are often used in such transformations. Under the optimised conditions, 25 monoallylated ketones were obtained in 16% to 98% yield and with high selectivity for the linear (E)–isomers.

AB - Whilst catalytic ketone allylation using palladium(0) is well–precedented, nickel(0)‐catalysed equivalents of such reactions remain scarce. We report here the first nickel‐catalysed allylation of ketones which uses an easily handled and inexpensive bench‐stable Ni(II) pre‐catalyst. This method avoids generation of stoichiometric by‐products via the use of readily available allyl alcohols, rather than the esters or related derivatives which are often used in such transformations. Under the optimised conditions, 25 monoallylated ketones were obtained in 16% to 98% yield and with high selectivity for the linear (E)–isomers.

KW - Allylation

KW - C−C coupling

KW - Ketone

KW - Nickel

KW - Sustainable catalysis

U2 - 10.1002/adsc.202400610

DO - 10.1002/adsc.202400610

M3 - Journal article

VL - 366

SP - 3833

EP - 3838

JO - Advanced Synthesis & Catalysis

JF - Advanced Synthesis & Catalysis

SN - 1615-4150

IS - 18

ER -