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Known substrate limitations: indole with ethyl α-diazobutanoate gave the product of N-H insertion in 29% yield and <1% ee; 6-(hydroxymethyl)- N -methylindole with ethyl α-diazo-5-methylhexanoate gave the product of O-H insertion in 41% yield and <1% ee; 1,2-dimethyl-6-(4,4,5,5-tetramethyl-1, 3,2-dioxaborolan-2-yl)-1 H -indole with ethyl α-diazo-5-methylhexanoate gave the desired C-H functionalization product in 81% yield, but only 13% ee; 5-nitro-1,2-dimethylindole with ethyl α-diazobutanoate did not give any intermolecular products.
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