Table 2. Mononitration of (Hetero)arenes with 2o^a,b.

^aStandard conditions I: 3 (1.0 equiv), 2o (1.2–1.5 equiv), Yb(OTf)₃ (10 mol %), MeCN (0.2 M), and 80 °C. Standard conditions II: 3 (1.0 equiv), 2o (2.0 equiv), In(OTf)₃ (20 mol %), HFIP (0.5 M), and 80 °C.

^bAll reactions were performed on a 0.2 mmol scale unless otherwise noted. Isolated yields were reported. The minor regioisomeric position is labeled.

^cGram scale.

^d1.2 equiv of 2o.

^eThe deiodinative nitration product 1-methoxy-2,4-dinitrobenzene (4ee′) was also isolated in a 24% yield.

^fThe deformylative nitration product 4ee′ was also isolated in a 15% yield.

^gIn(OTf)₃ (10 mol %), 2o (1.5 equiv), MeCN (0.2 M), and 100 °C.