Table 3.

Electrophile scope containing common heterocyclic pharmacophores and electrophilic arenes

All reactions were performed on 0.25 mmol scale, unless otherwise stated, in THF or dioxane (0.1M) under an argon atmosphere.

^aMethod A was used.

^bMethod B was used.

^cDecomposition observed after 14 days at room temperature – increased stability at −20 or −80 °C under argon (see Supplementary Handling of reagents section).

^dReactions were performed on gram scales (7 examples).

^ePerformed on >2 mmol scale.

^fPerformed on >1 mmol scale. Pharmaceutical scaffolds and intermediates are outlined in grey boxes. PG, protecting group; LG, leaving group; Het, heterocycle; Me, methyl; Ph, phenyl; t-Bu, tert-butyl; Bz, benzoyl; Ts, para-toluenesulfonyl (tosyl); Piv, pivaloyl; Bn, benzyl; NaHMDS, sodium bis(trimethylsilyl)amide; THF, tetrahydrofuran.