The document discusses the development of a tin-catalyzed method for the conjugate reduction of α,β-unsaturated ketones using organotin hydrides. Organotin reagents, particularly Bu3SnH, are widely used in organic synthesis but have toxicity concerns. Chemoselective catalytic reduction of conjugated α,β-unsaturated ketones to saturated ketones via a hydroboration/protodeboronation strategy. Organic Chemistry Frontiers 2016, 3 (1) , 14-18. Chemoselective Hydrosilylation of the α,β-Site Double Bond in α,β- and α,β,γ,δ-Unsaturated Ketones Catalyzed by Macrosteric Borane Promoted by Hexafluoro-2-propanol. Organotin hydrides are very good radical reducing agents due to the relatively weak, nonionic bond between tin and hydrogen (Bu 3 SnH 74 kcal/mol) that can cleave homolytically. Tributyltin hydride (Bu₃SnH) is defined as a versatile reagent used for replacing halogen atoms in organic molecules with hydrogen atoms, often requiring radical initiators or thermal conditions for reactions with iodides and bromides, while exhibiting high chemoselectivity towards various functional groups. Triphenyltin hydride was found to reduce the carbonarbon double bond (2), whereas tributyltin hydride, under the influence cf U.V. -irradiation, yielded mainly the 1,4dduct (3). the relatively well-understood, sometimes unique, chem- istry of tin, while greatly reducing the amount of orga- notin reagent that is required.We describe herein the have established that these two observations form the basis for a new catalytic process, the Bu3SnH-catalyzed, PhSiH3-mediated conjugate reduction of an R,â-unsatur- We demonstrate that a pentavalent phosphorus compound, tetraarylhydrophosphorane, is capable of catalyzing 1,4-reduction of α,β-unsaturated ketones in the presence of pinacolborane. The rhodium (III) complex (Cy3P)2Rh (H)Cl2 is an effective catalyst precursor for the hydrogenation of the double bond of alpha, beta-unsaturated aldehydes or ketones under mild... Cite Download(241.91 kB) Share Embed journal contribution posted on1996-09-20, 00:00authored byDavid S. Hays, Matthias Scholl, Gregory C. Fu Organotin Hydride-Catalyzed Conjugate Reduction of α,β-Unsaturated Ketones
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