Reduction of salicylaldehyde using a pinacol-derived chlorosilane\lewis base system

Benedicta Assoah, Nuno Rafael Candeias

    Research output: Other conference contributionPaper, poster or abstractScientific

    Abstract

    Reduction of carbonyl functionality into a hydroxyl moiety1 has been studied with both Lewis base2 and Lewis acid3 mediated hydrosilylation protocols. As part of an ongoing research investigating the intramolecular hydride delivery of a pinacol-derived chlorosilane, we seek to explore the Lewis acidity of hydrosilyl ethers derived from this novel cyclic chlorosilane in Lewis base activated systems for the anchimeric assistance reduction of carbonyl compounds.
    Reduction of salicylaldehyde to salicyl alcohol was achieved in 70% upon use of trimethylamine as Lewis base and hydrochloric acid capturing agent. Screening of other Lewis bases (PPh3, DBU, Hünig’s base, Pyridine, Pyridine N-oxide, HMPA, etc) and optimization of reaction conditions with the newly developed chlorosilane will be presented.
    Original languageEnglish
    Publication statusUnpublished - 27 Aug 2017
    EventSWISS SUMMER SCHOOL 2017: TRENDS IN ORGANIC SYNTHESIS - EUROTEL-VICTORIA, VILLARS SUN OLLON, Switzerland
    Duration: 27 Aug 201731 Aug 2017
    http://scg.ch/index.php?option=com_content&view=article&id=1648:swiss-summer-school-2017-trends-in-organic-synthesis-august-27-31-2017&catid=74:fr-news&Itemid=244&lang=en

    Conference

    ConferenceSWISS SUMMER SCHOOL 2017
    CountrySwitzerland
    CityVILLARS SUN OLLON
    Period27/08/1731/08/17
    Internet address

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