Related Experiment Video
Updated: Sep 13, 2025

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
Published on: July 27, 2022
Tandem Oligomerization-Hydrogenation Using Brønsted Acidic Iridium Hydride Catalysts
Austin J Leitgeb1, Scott M Chapp1, Caleb D Fast1
1Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, United States.
None:
Cationic iridium complexes bearing the tris-[3,5-bis-(trifluoromethyl)-phenyl]-phosphine ligand unexpectedly give acidic metal hydrides. Net-dihydrogen heterolysis at such complexes provides hydrogenation catalysis by an ionic mechanism. The direct reduction of isobutene competes with cationic oligomerization to give the gasoline additive isooctane (2,4,4-trimethylpentane) as a major product of a tandem oligomerization/hydrogenation sequence. Mechanistic experiments argue for the role of neutral iridium hydrides generated by the proton transfer of a cationic hydride precursor to an olefin substrate.
More Related Videos
10:39Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction
Published on: August 23, 2018
11:44Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
Published on: March 20, 2014
Related Concept Videos
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Radical Anti-Markovnikov Addition to Alkenes: Mechanism
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.