Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 31, Pages 10727-10731Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201903392
Keywords
allylation; latent nucleophiles; Lewis base catalysis; nitrogen heterocycles; nucleophilic substitution
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Funding
- Carl-Zeiss Foundation (endowed professorship)
- Friedrich Schiller University Jena
- State of Thuringia
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Latent nucleophiles are compounds that are themselves not nucleophilic but can produce a strong nucleophile when activated. Such nucleophiles can expand the scope of Lewis base catalyzed reactions. As a proof of concept, we report that N-silyl pyrroles, indoles, and carbazoles serve as latent N-centered nucleophiles in substitution reactions of allylic fluorides catalyzed by Lewis bases. The reactions feature broad scopes for both reaction partners, excellent regioselectivities, and produce enantioenriched N-allyl pyrroles, indoles, and carbazoles when chiral cinchona alkaloid catalysts are used.
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