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Abstract
Selective functionalization of indole C3-C bond with
aromatic/heteroaromatic 1,2-diketones has been uncovered for the first time. Earth crust abundant first-row transition metal cobalt catalyst has been demonstrated as an effective catalyst for this unusual transformation. Furthermore, the use of easily available weakly coordinating groups such as ketone and ester was found to be effective. The key feature of this methodology is the in-situ generation of water from hexafluoro-2-propanol and the removal of the pivaloyl/ester group in a decarbonylative manner at a lower temperature. In addition, photophysical studies show the potential utility of indole (C3)-acyloin and indolo-fused carbazole, in photovoltaic and optoelectronic applications
Supplementary materials
Title
Cobalt catalyzed decarbonylative ipso C-C bond functionalization: Synthesis of Indole C-3 functionalized acyloins using 1,2-diketone
Description
The cobalt-catalyzed selective indole C(3)-C bond functionalization has been achieved through a decarbonylative pathway. Where 1,2- diketones (acyclic and cyclic) have been transpired as effective reaction partners for this conversion. The in-situ generation of water is the key success of this decarbonylative conversion. This protocol gives easy access to build indole C(3)-acyloin and indolo-fused carbazole motifs. Also, the photophysical studies highlight their usefulness in pharmaceutical and material science aspects.
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