American Chemical Society
ol0c02600_si_001.pdf (5.34 MB)

B(C6F5)3‑Catalyzed β‑Functionalization of Pyrrolidines Using Isatins via Borrowing Hydrogen: Divergent Access to Substituted Pyrrolidines and Pyrroles

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journal contribution
posted on 2020-09-29, 13:34 authored by Yong Chen, Hai-Lun Wan, Yuan Huang, Song Liu, Feiyi Wang, Cuifen Lu, Junqi Nie, Zuxing Chen, Guichun Yang, Chao Ma
We report herein a B­(C6F5)3-catalyzed redox-neutral β-functionalization of pyrrolidines with isatins. Under transition-metal- and oxidant-free conditions at ambient temperature, a series of pyrrolidines bearing a functionalized exocyclic alkene are accessed in high efficiency through a borrowing hydrogen process. A simple switch to higher reaction temperature in a one-pot procedure also provides access to a diverse array of C(3)-functionalized pyrroles while liberating water and hydrogen gas as the only byproducts.