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

Research output: Other conference contributionPaper, poster or abstractScientific

Details

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

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.