4.8 Article

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

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ORGANIC LETTERS
卷 22, 期 20, 页码 7797-7803

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c02600

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  1. National Natural Science Foundation of China [21901066, 21702053]
  2. Hubei Provincial Department of Education project [Q20181003]

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We report herein a B(C6F5)(3)-catalyzed redox-neutral beta-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.

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