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- Publisher
- Royal Society of Chemistry
- Copyright
- This journal is © The Royal Society of Chemistry
- ISSN
- 2041-6520
- eISSN
- 2041-6539
- DOI
- 10.1039/c8sc01315b
- Publisher site
- See Article on Publisher Site
Abstract
Recently, Chirik and co-workers reported bis(phosphine)cobalt dialkyl complexes for the hydrogenation of alkenes under mild conditions (). A significant activating effect by hydroxyl groups was observed for the cobalt catalysts. Ether, ester, or ketone groups did not provide such an effect. The reported cobalt dialkyl catalyst dppeCo(CH2SiMe3)2 (, dppe = 1,2-bis(diphenylphosphino)ethane) catalyses hydrogenation of terpinen-4-ol providing 99% conversion (entry 2, ), whereas the corresponding methyl ether displays <5% conversion despite higher catalyst loading and longer reaction time (entry 3, ). Interestingly, hydrogenation of terpinen-4-ol gives a high diastereoselectivity with a diastereomeric ratio (d.r.) of 99.8 : 0.2 (entry 2, ). Compared to tri-substituted alkenes, di-substituted terminal alkenes could be hydrogenated without a hydroxyl group present (entry 4, ).
Journal
Chemical Science – Royal Society of Chemistry
Published: Jun 6, 2018