Dehydrogenative Coupling Reactions with Guanidino-Functionalized Aromatics.

Authors :: Walter P
Schulz M
Hübner O
Poddelskii A
Kaifer E
Himmel HJ
Source :: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Dec 18; Vol. 30 (71), pp. e202402917. Date of Electronic Publication: 2024 Nov 13.
Publication Year :: 2024
Abstract: Dehydrogenative coupling (DC) reactions are of importance for the construction of new carbon-element bonds in synthetic organic chemistry. In this work, we report on the synthesis and characterization of several redox-active guanidino-functionalized aromatic molecules (GFAs) for use in DC (C-C and C-O) reactions. In a systematic approach, we first characterize the new DC reagents in all relevant redox and protonation states, and compare their performance in competitive test proton-coupled electron transfer (PCET) reactions. Then, their use in four different DC reactions with different mechanisms is evaluated.<br /> (© 2024 The Author(s). Chemistry - A European Journal published by Wiley-VCH GmbH.)