An efficient and mild Ir(III)-catalyzed, chelation assisted C–H alkynylation of arenes has been developed using hypervalent iodine alkynes as alkynylating reagents. A broad scope of N-phenyl-2-aminopyridines and 2-phenoxypyridines has been established as effective substrates for this C–H functionalization and the desired alkynylated products were isolated in moderate to high yields.