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. 2018 Mar 2;20(5):1338-1341.
doi: 10.1021/acs.orglett.8b00070. Epub 2018 Feb 12.

Ni-Catalyzed Electrochemical Decarboxylative C-C Couplings in Batch and Continuous Flow

Hui Li  1 , Christopher P Breen  1   2 , Hyowon Seo  2 , Timothy F Jamison  2 , Yuan-Qing Fang  1 , Matthew M Bio  1
Affiliations

Ni-Catalyzed Electrochemical Decarboxylative C-C Couplings in Batch and Continuous Flow

Hui Li et al. Org Lett. .

Abstract

An electrochemically driven, nickel-catalyzed reductive coupling of N-hydroxyphthalimide esters with aryl halides is reported. The reaction proceeds under mild conditions in a divided electrochemical cell and employs a tertiary amine as the reductant. This decarboxylative C(sp3)-C(sp2) bond-forming transformation exhibits excellent substrate generality and functional group compatibility. An operationally simple continuous-flow version of this transformation using a commercial electrochemical flow reactor represents a robust and scalable synthesis of value added coupling process.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Nickel-catalyzed sp3–sp2 cross-couplings using carboxylic acids/derivatives and aryl halides as coupling partners.
Figure 2
Figure 2
Proposed electrochemical-driven nickel-catalyzed decarboxylative arylation unit steps.
Scheme 1
Scheme 1. Reaction Scope of Nickel-Catalyzed Electrochemical Decarboxylative Arylations
Figure 3
Figure 3
Kinetic profile of decarboxylative coupling between NHP ester and iodobenzene (“e” denotes electron).
See this image and copyright information in PMC

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