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Regioselective Hydroalkylation of Vinylarenes by Cooperative Cu and Ni Catalysis

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Regioselective Hydroalkylation of Vinylarenes by Cooperative Cu and Ni Catalysis. / Ravn, Anne K.; Johansen, Martin B.; Skrydstrup, Troels.

In: Angewandte Chemie - International Edition, Vol. 61, No. 4, e202112390, 21.01.2022.

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

Vancouver

Ravn AK, Johansen MB, Skrydstrup T. Regioselective Hydroalkylation of Vinylarenes by Cooperative Cu and Ni Catalysis. Angewandte Chemie - International Edition. 2022 Jan 21;61(4):e202112390. doi: 10.1002/anie.202112390

Author

Ravn, Anne K. ; Johansen, Martin B. ; Skrydstrup, Troels. / Regioselective Hydroalkylation of Vinylarenes by Cooperative Cu and Ni Catalysis. In: Angewandte Chemie - International Edition. 2022 ; Vol. 61, No. 4.

Bibtex

@article{2b2074d1525541c6b5f37fd8b83530c6,

title = "Regioselective Hydroalkylation of Vinylarenes by Cooperative Cu and Ni Catalysis",

abstract = "Disclosed here is a dual copper and nickel catalytic system with a silyl hydride source for promoting the linear selective hydroalkylation of vinylarenes. This carbon–carbon bond-forming protocol is applied to couple a variety of functionalized vinylarenes with alkyl halides applying a nickel(II) NNN pincer complex in the presence of an NHC-ligated copper catalyst. This combination allows for a 1 mol % loading of the nickel catalyst leading to turnover numbers of up to 72. Over 40 examples are presented, including applications for pharmaceutical diversification. Labeling experiments demonstrated the regioselectivity of the reaction and revealed that the copper catalyst plays a crucial role in enhancing the rate for formation of the reactive linear alkyl nickel complex. Overall, the presented work provides a complimentary approach for hydroalkylation reactions, whilst providing a preliminary mechanistic understanding of the cooperativity between the copper and nickel complexes.",

keywords = "dual catalysis, hydroalkylation, metal hydrides, regioselectivity, vinylarenes",

author = "Ravn, {Anne K.} and Johansen, {Martin B.} and Troels Skrydstrup",

note = "Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH",

year = "2022",

month = jan,

day = "21",

doi = "10.1002/anie.202112390",

language = "English",

volume = "61",

journal = "Angewandte Chemie International Edition",

issn = "1433-7851",

publisher = "Wiley - VCH Verlag GmbH & CO. KGaA",

number = "4",

}

RIS

TY - JOUR

T1 - Regioselective Hydroalkylation of Vinylarenes by Cooperative Cu and Ni Catalysis

AU - Ravn, Anne K.

AU - Johansen, Martin B.

AU - Skrydstrup, Troels

PY - 2022/1/21

Y1 - 2022/1/21

N2 - Disclosed here is a dual copper and nickel catalytic system with a silyl hydride source for promoting the linear selective hydroalkylation of vinylarenes. This carbon–carbon bond-forming protocol is applied to couple a variety of functionalized vinylarenes with alkyl halides applying a nickel(II) NNN pincer complex in the presence of an NHC-ligated copper catalyst. This combination allows for a 1 mol % loading of the nickel catalyst leading to turnover numbers of up to 72. Over 40 examples are presented, including applications for pharmaceutical diversification. Labeling experiments demonstrated the regioselectivity of the reaction and revealed that the copper catalyst plays a crucial role in enhancing the rate for formation of the reactive linear alkyl nickel complex. Overall, the presented work provides a complimentary approach for hydroalkylation reactions, whilst providing a preliminary mechanistic understanding of the cooperativity between the copper and nickel complexes.

AB - Disclosed here is a dual copper and nickel catalytic system with a silyl hydride source for promoting the linear selective hydroalkylation of vinylarenes. This carbon–carbon bond-forming protocol is applied to couple a variety of functionalized vinylarenes with alkyl halides applying a nickel(II) NNN pincer complex in the presence of an NHC-ligated copper catalyst. This combination allows for a 1 mol % loading of the nickel catalyst leading to turnover numbers of up to 72. Over 40 examples are presented, including applications for pharmaceutical diversification. Labeling experiments demonstrated the regioselectivity of the reaction and revealed that the copper catalyst plays a crucial role in enhancing the rate for formation of the reactive linear alkyl nickel complex. Overall, the presented work provides a complimentary approach for hydroalkylation reactions, whilst providing a preliminary mechanistic understanding of the cooperativity between the copper and nickel complexes.

KW - dual catalysis

KW - hydroalkylation

KW - metal hydrides

KW - regioselectivity

KW - vinylarenes

UR - http://www.scopus.com/inward/record.url?scp=85120894358&partnerID=8YFLogxK

U2 - 10.1002/anie.202112390

DO - 10.1002/anie.202112390

M3 - Journal article

C2 - 34727415

AN - SCOPUS:85120894358

VL - 61

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

SN - 1433-7851

IS - 4

M1 - e202112390

ER -