Nickelaelectro‐Catalyzed C─H Activation to <i>β</i>‐Arylated Pyrroles <i>via</i> Multiple Dehydrogenation
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
Authors (7)
Kazuhiro Okamoto
Department of Science, University of Toyama, 3190 Gofuku, Toyama 930-0887, Japan
Simon L. Homölle
Wöhler Research Institute for Sustainable Chemistry (WISCh) Georg‐August‐Universität Göttingen Tammannstrasse 2 37077 Göttingen Germany
Tristan von Münchow
University of Bologna, Department of Industrial Chemistry Toso Montanari, via Piero Gobetti 85, 40129 Bologna, Italy
Sven E. Peters
Wöhler Research Institute for Sustainable Chemistry (WISCh) Georg‐August‐Universität Göttingen Tammannstrasse 2 37077 Göttingen Germany
Sven Trienes
Wöhler Research Institute for Sustainable Chemistry (WISCh) Georg‐August‐Universität Göttingen Tammannstraße 2 37077 Göttingen Germany
João C. A. Oliveira
Wöhler Research Institute for Sustainable Chemistry
Lutz Ackermann
Institut für Organische und Biomolekulare Chemie (IOBC)