Nickelaelectro‐Catalyzed C─H Activation to <i>β</i>‐Arylated Pyrroles <i>via</i> Multiple Dehydrogenation

K Kazuhiro Okamoto (Department of Science, University of Toyama, 3190 Gofuku, Toyama 930-0887, Japan) S Simon L. Homölle (Wöhler Research Institute for Sustainable Chemistry (WISCh) Georg‐August‐Universität Göttingen Tammannstrasse 2 37077 Göttingen Germany) T Tristan von Münchow (University of Bologna, Department of Industrial Chemistry Toso Montanari, via Piero Gobetti 85, 40129 Bologna, Italy) S Sven E. Peters (Wöhler Research Institute for Sustainable Chemistry (WISCh) Georg‐August‐Universität Göttingen Tammannstrasse 2 37077 Göttingen Germany) S Sven Trienes (Wöhler Research Institute for Sustainable Chemistry (WISCh) Georg‐August‐Universität Göttingen Tammannstraße 2 37077 Göttingen Germany) J João C. A. Oliveira (Wöhler Research Institute for Sustainable Chemistry) L Lutz Ackermann (Institut für Organische und Biomolekulare Chemie (IOBC))

Abstract

AbstractNickel electrocatalysis has emerged as a powerful strategy for sustainable C─H activation, offering an environmentally benign alternative to traditional methods based on stoichiometric oxidants. We, herein, report a nickela‐electrocatalyzed approach for the expedient synthesis of β‐arylated pyrroles via a unique multiple dehydrogenative C─H activation approach. Hence, direct C─C bond formation between pyrroles and arenes was enabled, obviating the need for prefunctionalized substrates. The reaction proceeded under electrochemical conditions in a user‐friendly undivided cell, utilizing electricity as a traceless oxidant. Mechanistic studies, including cyclic voltammetry, provided support for a nickel(II/III/IV) regime, wherein anodic oxidation facilitates the dehydrogenation and C─H activation paired with the valuable hydrogen evolution reaction (HER). Our findings highlight the potential of electrocatalysis to unlock distinct reaction manifolds and provides a sustainable platform for accessing complex heteroaryl frameworks.

Article Details

Volume / Issue Vol. 64, Issue 40
Published September 26, 2025
ISSN 1433-7851
Publisher Wiley

Journal Info

Angewandte Chemie International Edition

Wiley

ISSN: 1433-7851 Physical Sciences

Authors (7)

K

Kazuhiro Okamoto

Department of Science, University of Toyama, 3190 Gofuku, Toyama 930-0887, Japan

S

Simon L. Homölle

Wöhler Research Institute for Sustainable Chemistry (WISCh) Georg‐August‐Universität Göttingen Tammannstrasse 2 37077 Göttingen Germany

T

Tristan von Münchow

University of Bologna, Department of Industrial Chemistry Toso Montanari, via Piero Gobetti 85, 40129 Bologna, Italy

S

Sven E. Peters

Wöhler Research Institute for Sustainable Chemistry (WISCh) Georg‐August‐Universität Göttingen Tammannstrasse 2 37077 Göttingen Germany

S

Sven Trienes

Wöhler Research Institute for Sustainable Chemistry (WISCh) Georg‐August‐Universität Göttingen Tammannstraße 2 37077 Göttingen Germany

J

João C. A. Oliveira

Wöhler Research Institute for Sustainable Chemistry

L

Lutz Ackermann

Institut für Organische und Biomolekulare Chemie (IOBC)