Directed Nickel-Catalyzed Selective Arylhydroxylation of Unactivated Alkenes under Air
Yihua Wang1, Cong Lin1, Zongxu Zhang1
1College of Chemistry and Chemical Engineering, Jiangxi Science & Technology Normal University, Nanchang 330013, China.
Abstract:
An expeditious and novel nickel-catalyzed selective arylhydroxylation of unactivated alkenes with arylboronic acids was developed. This protocol is compatible with β,γ- and γ,δ-alkene amides, including traditionally challenging internal alkenes, to provide important β-arylethylalcohol scaffolds. The free hydroxyl group in the final product could be smoothly further transformed into other functional groups. Control experiments indicated that the oxygen atom of the hydroxyl group in the product is derived from the oxygen in the air.
More Related Videos
07:30A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
Published on: January 21, 2020
07:06A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Related Concept Videos
02:24Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
02:17Reduction 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...
02:47Alkynes 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.
02:13Reduction of Alkenes: Catalytic Hydrogenation
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
01:25Radical Anti-Markovnikov Addition to Alkenes: Overview
02:44Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide