4.8 Article

Fluorinated Sulfinates as Source of Alkyl Radicals in the Photo-Enantiocontrolled β-Functionalization of Enals

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出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202112632

关键词

Asymmetric Catalysis; Fluorination; Photocatalysis; Visible Light

资金

  1. European Research Council (ERC-CoG) [647550]
  2. Spanish Government [RTI2018-095038-B-I00]
  3. Comunidad de Madrid
  4. European Structural Funds [S2018/NMT-4367]

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In this study, a convenient strategy using gem-difluorinated sulfinates as upgrading-masks is reported, which allows the decomposition of precursors into corresponding alkyl radicals. The stereocontrolled light-driven insertion of gem-difluoro derivatives into unsaturated aldehydes is achieved.
The generation of sulfonyl radicals has long been known as a flexible strategy in a wide range of different sulfonylative transformations. Meanwhile their use in alkylation processes has been somehow limited due to their inherent difficulty in evolving to less-stable radicals after sulfur dioxide extrusion. Herein we report a convenient strategy that involves gem-difluorinated sulfinates as an upgrading-mask, allowing these precursors to decompose into their corresponding alkyl radicals. The electron-donor character of sulfinates in the formation of an electron donor-acceptor (EDA) complex with transient iminium ions is displayed, achieving the first example of a stereocontrolled light-driven insertion of gem-difluoro derivatives into unsaturated aldehydes. This methodology is compatible with flow conditions, maintaining identical levels of enantiocontrol.

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