Cross‐Dehydrogenative Homocoupling of 2‐Aryl‐N‐heterocycles and Application to the Synthesis of Phenylpyridine Borane Dimers. Issue 17 (27th November 2022)

• Record Type: Journal Article
• Authors: Gao, Longhui; Feuillastre, Sophie; Clavier, Gilles; Pieters, Grégory
• Is Part Of: European journal of organic chemistry. Volume 26:Issue 17(2023)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-11-27
• Subjects: Cross-dehydrogenative coupling -- C−H activation -- DFT calculation -- Heterogeneous catalysis -- Fluorescent emitters; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202201164
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A method for the synthesis of 2‐aryl‐N‐heterocyclic dimers via a cross‐dehydrogenative homocoupling (homo‐CDC) has been developed using commercially available Ruthenium on charcoal as catalyst and iron trichloride as oxidant. A large variety of heterocyclic scaffolds and functional groups are tolerated and a complete regioselectivity resulting from the activation of the less sterically hindered C−H bonds was observed for meta ‐substituted substrates. Starting from several homocoupling products obtained, a series of pyridine‐borane complexes was synthesized and the impact of the dimerization on their photophysical properties was studied and rationalized using theoretical calculations. Abstract : This work reports a regioselective cross‐dehydrogenative homocoupling reaction using a heterogeneous Ru catalyst and iron trichloride as oxidant to gain access to various 2‐aryl‐N‐heterocyclic dimers. Several homocoupling products obtained were then used to synthesize a series of pyridine‐borane complexes and the impact of the dimerization on their photophysical properties was studied and rationalized by using theoretical calculations.