jo0c01363_si_001.pdf (12.71 MB)
Elemental-Sulfur-Incorporated Cyclizations of Pyrrolidines Leading to Thienopyrroles
journal contribution
posted on 2020-08-12, 10:04 authored by Yuanyuan Yue, Huibin Shao, Zhixian Wang, Ke Wang, Le Wang, Kelei Zhuo, Jianming LiuWe report, herein, the synthesis
of thieno[3,2-b]pyrroles from the direct oxidative
[4 + 1] cyclization of 2-alkynyl
pyrrolidines with elemental sulfur. This transformation likely originates
from electrophilic attack at the β-position of pyrrolidine followed
by an intramolecular thienannulation to deliver the desired product.
Mechanistic investigation suggests that the present reaction involves
the formation of dihydrothieno[3,2-b]pyrrole as an
intermediate.