Nickel Catalyzed Regiodivergent Cross-Coupling Alkylation of Aryl Halides with Redox-Active Imines

Long Huang; Rajesh Kancherla; Magnus Rueping

doi:10.1021/acscatal.2c03396

Nickel Catalyzed Regiodivergent Cross-Coupling Alkylation of Aryl Halides with Redox-Active Imines

Long Huang, Rajesh Kancherla, Magnus Rueping

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

5 Scopus citations

Abstract

The advent and development of photoredox/nickel synergistic catalysis have enabled the use of various alkyl radical precursors in the cross-coupling arylation, yet none has addressed the challenge of regiodivergent synthesis. Herein, we disclose a visible light nickel-catalyzed protocol for the deaminative cross-coupling of redox-active imines with various electrophiles that allow for the rapid construction of C(sp3) enriched arene architectures in a regiodivergent manner. Key to the success of this protocol is the combination of a readily available organic photocatalyst and a Lewis acid additive. As an additional approach to alkylarenes, we also showcase that the nature of electrophiles dictates the regiochemical outcome.

Original language	English (US)
Pages (from-to)	11563-11572
Number of pages	10
Journal	ACS Catalysis
DOIs	https://doi.org/10.1021/acscatal.2c03396
State	Published - Sep 8 2022

Bibliographical note

KAUST Repository Item: Exported on 2022-09-12
Acknowledged KAUST grant number(s): URF/1/4405
Acknowledgements: This work was financially supported by the King Abdullah University of Science and Technology (KAUST), Saudi Arabia, Office of Sponsored Research (URF/1/4405).

ASJC Scopus subject areas

Catalysis

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10.1021/acscatal.2c03396

https://repository.kaust.edu.sa/bitstream/10754/681132/1/Manuscript-accepted%20%281%29.pdf

Cite this

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title = "Nickel Catalyzed Regiodivergent Cross-Coupling Alkylation of Aryl Halides with Redox-Active Imines",

abstract = "The advent and development of photoredox/nickel synergistic catalysis have enabled the use of various alkyl radical precursors in the cross-coupling arylation, yet none has addressed the challenge of regiodivergent synthesis. Herein, we disclose a visible light nickel-catalyzed protocol for the deaminative cross-coupling of redox-active imines with various electrophiles that allow for the rapid construction of C(sp3) enriched arene architectures in a regiodivergent manner. Key to the success of this protocol is the combination of a readily available organic photocatalyst and a Lewis acid additive. As an additional approach to alkylarenes, we also showcase that the nature of electrophiles dictates the regiochemical outcome.",

author = "Long Huang and Rajesh Kancherla and Magnus Rueping",

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doi = "10.1021/acscatal.2c03396",

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AU - Kancherla, Rajesh

AU - Rueping, Magnus

N1 - KAUST Repository Item: Exported on 2022-09-12 Acknowledged KAUST grant number(s): URF/1/4405 Acknowledgements: This work was financially supported by the King Abdullah University of Science and Technology (KAUST), Saudi Arabia, Office of Sponsored Research (URF/1/4405).

PY - 2022/9/8

Y1 - 2022/9/8

N2 - The advent and development of photoredox/nickel synergistic catalysis have enabled the use of various alkyl radical precursors in the cross-coupling arylation, yet none has addressed the challenge of regiodivergent synthesis. Herein, we disclose a visible light nickel-catalyzed protocol for the deaminative cross-coupling of redox-active imines with various electrophiles that allow for the rapid construction of C(sp3) enriched arene architectures in a regiodivergent manner. Key to the success of this protocol is the combination of a readily available organic photocatalyst and a Lewis acid additive. As an additional approach to alkylarenes, we also showcase that the nature of electrophiles dictates the regiochemical outcome.

AB - The advent and development of photoredox/nickel synergistic catalysis have enabled the use of various alkyl radical precursors in the cross-coupling arylation, yet none has addressed the challenge of regiodivergent synthesis. Herein, we disclose a visible light nickel-catalyzed protocol for the deaminative cross-coupling of redox-active imines with various electrophiles that allow for the rapid construction of C(sp3) enriched arene architectures in a regiodivergent manner. Key to the success of this protocol is the combination of a readily available organic photocatalyst and a Lewis acid additive. As an additional approach to alkylarenes, we also showcase that the nature of electrophiles dictates the regiochemical outcome.

UR - http://hdl.handle.net/10754/681132

UR - https://pubs.acs.org/doi/10.1021/acscatal.2c03396

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JO - ACS Catalysis

JF - ACS Catalysis

ER -

Nickel Catalyzed Regiodivergent Cross-Coupling Alkylation of Aryl Halides with Redox-Active Imines

Abstract

Bibliographical note

ASJC Scopus subject areas

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