Hydrogen bonding mediated electron donor-acceptor acceptor catalysis in hydrosulfonylation and sulfonyl
Qiang Hu1, Ying Li1, Tianlong Zeng1
1College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, China.
Abstract:
Electron donor-acceptor (EDA) acceptor catalysis remains significantly less developed than donor catalysis. Herein, a hydrogen-bond-mediated EDA acceptor catalysis using readily available 4,4'-di-tert-butyl-2,2'-bipyridine (dtbbpy) or 4-tert-butylpyridine as the acceptor catalyst is developed, enabling the hydrosulfonylation of unactivated olefins and sulfonyl dehydrogenation of styrenes, utilizing sodium sulfinates as the sulfonyl source. The reaction proceeds under mild conditions. A broad range of functional groups is well tolerated, affording good to excellent yields. Preliminary mechanistic investigations, including both computational studies and experiments, indicate that hydrogen bonding between sulfinic acid and the acceptor catalyst may facilitate the formation of a photoresponsive EDA complex and the subsequent photo-induced radical generation.
More Related Videos
Related Concept Videos
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...
02:44Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
03:08Hydroboration-Oxidation of Alkenes
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...
02:36Regioselectivity 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 stereochemistry.
02:34Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration