Related Experiment Video
Updated: Sep 5, 2026

Light-driven Enzymatic Decarboxylation
Published on: May 22, 2016
A General Photoredox Platform for the Hydroarylation of Olefins
Yi-Lun Li1, Johnny Z Wang1, David W C MacMillan1
1Merck Center for Catalysis at Princeton University , Princeton, New Jersey08544, United States.
Abstract:
Alkene hydroarylation provides a direct strategy for merging aryl groups with alkene-derived C(sp3)-rich fragments, yet general methods that employ abundant aryl bromides across diverse alkene classes remain elusive. Herein, we report XAT-Heck, a radical hydroarylation platform that couples aryl bromides with alkenes under mild photoredox conditions through halogen-atom transfer (XAT)-enabled aryl radical generation. The method accommodates terminal, internal, and gem-disubstituted alkenes, as well as a broad range of heteroaryl and aryl bromides. Chemical-space mapping further supports the broad coverage of commercially available olefin and aryl bromide space. The versatility of this platform is showcased through deuterium incorporation, medium-ring formation, late-stage functionalization, and proteolysis-targeting chimera (PROTAC) library construction.
Related Concept Videos
Reduction 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 surface of...
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...
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
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.
Hydroboration-Oxidation of Alkenes
Reduction 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.
![[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
