Rhodium-catalyzed C–H functionalization of heteroarenes using indoleBX hypervalent iodine reagents

• Erwann Grenet,
• Ashis Das,
• Paola Caramenti and
• Jérôme Waser

Beilstein J. Org. Chem. 2018, 14, 1208–1214, doi:10.3762/bjoc.14.102

• regioselectivity for the C-6 position of bipyridinones and the C-8 position of quinoline N-oxides and tolerated a broad range of functionalities, such as halogens, ethers, or trifluoromethyl groups. Keywords: C–H activation; hypervalent iodine; indoleBX; indoles; pyridinones; rhodium catalysis; Introduction

• develop a new C–H heteroarylation of pyridinones. Herein, we report the selective C–H heteroarylation of the C-6 position of bipyridinones by a rhodium-catalyzed reaction with indoleBX (reaction 2, Scheme 1A). In addition, we demonstrate that the mild conditions developed allow the heteroarylation of the

• building blocks in the search for new bioactive compounds. Results and Discussion We started the studies on C–H indolation with the optimization of the reactions conditions (Table 1) for the coupling of [1,2'-bipyridin]-2-one (5a) with Me-indoleBX 6a, easily obtained from commercially available 1