Directed lithiation of N-benzenesulfonyl-3-bromopyrrole. electrophile-controlled regioselective functionalization via dynamic equilibrium between C-2 and C-5 lithio species.
Directed lithiation of N-benzenesulfonyl-3-bromopyrrole (1) with LDA in THF at -78 degrees C generated C-2 lithio species 3 selectively. Reactions of 3 with reactive electrophiles produced the corresponding 2-functionalized pyrroles 4. On the other hand, quenching with less reactive electrophiles generated the corresponding 5-substituted pyrroles 5. The latter unusual functionalization at C-5 could be rationalized by dynamic equilibrium between C-2 and C-5 lithio species.
Fukuda
Tsutomu
T
Graduate School of Science and Technology, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan.
Ohta
Takeshi
T
Sudo
Ei-Ichi
E
Iwao
Masatomo
M