Table 1.

Substrate scope for heteroarene C–H etherification using optimized halogen transfer reagents.^a

^aReactions conducted on 0.5 to 1 mmol scale of heteroarene; yields are of isolated products; reaction conducted at 60 °C for 3 h for Table 1a and at 25 °C for 20 h for Table 1b and 1c.

^b18-crown-6 (1.5 equiv) additive used.

^cSide products (20% total) from 2-substitution of the starting material observed.

^d2 equiv of alcohol used.

^eDMF used as solvent.

^fReaction conducted at 60 °C.

^gReaction conducted with 2 equiv pyridazine and 1 equiv alcohol; product forms in 4:1 ratio to other aryl ethers.

^hProduct forms in 6:1 ratio to other aryl ethers. See Supporting Information for full details.