Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 15, Pages 5095-5099Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201900659
Keywords
carbohalogenation; dearomative reaction; diastereoselective catalysis; indoles; nickel
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Funding
- Natural Science and Engineering Research Council (NSERC)
- Alphora Research Inc.
- Province of Ontario
- Science Foundation Ireland (SFI) [12/RC/2275]
- University of Toronto
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A diastereoselective dearomative carboiodination reaction is reported. We report a novel metal-catalyzed approach to install reactive secondary benzylic iodides. Utilizing the unique reactivity of nickel, we have expanded the carboiodination reaction to non-activated aromatic double bonds forming a previously unattainable class of iodides. We also report a broadly applicable method to avoid the use of a metallic reducing agent by utilizing an alkyl phosphite as the ligand. The reaction is thought to proceed through a syn intramolecular carbonickelation across a 2-substituted indole followed by a diastereoretentive reductive elimination of the carbon-iodine bond. The complex iodinated indolines generated in the reaction were obtained in moderate to good yields and good to excellent diastereoselectivity. The products were easily functionalized by a variety of synthetic methods.
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