Jump to main content
Jump to site search


Pd-Catalyzed C–H arylation of pyridazine-based fused 1,2,4-triazoles: overriding selectivity at the usual position by undermining of preferred chelate formation

Author affiliations

Abstract

The applicability of C–H functionalization to medicinally important 2-pyridyl-based N-heterocycles suffers from severe challenges owing to the high Lewis basicity of the N-atom. This arrests catalytic activity and yields undesirable positional selectivity due to preferential chelate formation. In this regard, we report a novel palladium(II)-catalyzed arylation strategy on multiple-N-containing pyridazines by over-riding the functionalization due to a chelated palladacycle. We report a regioselective mono-arylation at the 8-position of diphenyl azolopyridazines without any ortho-C–H activation on the proximal phenyl groups. This methodology presents a broad arylation scope with uncompromised yield and positional selectivity, including the heteroarylation of N-heterocycles, which is an unprecedented feat for these types of molecules.

Graphical abstract: Pd-Catalyzed C–H arylation of pyridazine-based fused 1,2,4-triazoles: overriding selectivity at the usual position by undermining of preferred chelate formation

Back to tab navigation

Supplementary files

Publication details

The article was received on 10 Aug 2017, accepted on 18 Sep 2017 and first published on 18 Sep 2017


Article type: Communication
DOI: 10.1039/C7CC06226E
Citation: Chem. Commun., 2017, Advance Article
  •   Request permissions

    Pd-Catalyzed C–H arylation of pyridazine-based fused 1,2,4-triazoles: overriding selectivity at the usual position by undermining of preferred chelate formation

    R. Srinivasan, A. Dey, N. S. Nagarajan, R. S. Kumaran, T. Gandhi and D. Maiti, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC06226E

Search articles by author

Spotlight

Advertisements