Hydroalkylation of alkenes

Lanman HE, Nguyen RV, Yao X et al (2008) Evaluating Lewis acid catalyzed hydroalkylation of alkenes in neat and in ionic Hqttids. 1 Mol Catal A Chem 279 218-222... 

Representative procedure for the gold-catalyzed hydroalkylation of alkenes. 2-Cyclooct-2-enyl-I,3-diphenylpropane-l,3-dion ... 

Sames and coworkers have very recently introduced BF3 OEt2 catalysis to promote room temperature hydroalkylation of electron deflcient olefins as a formal sp C-H functionalization process. Coordination of the Lewis acid to the alkene moiety of the tetrahydropyran (121) facilitates a 1,5-hydride shift to afford a zwitterionic species, (122), which is followed by nucleophilic attack at the oxocarbonium center to furnish the requisite spirocyclic pyran (123) (Equation 74) [77]. 

Hydroformylation and Hydrogenation. Octacarbonyldicobalt catalyzes a wide range of reactions of carbon monoxide (alone or with hydrogen), "" of whieh the best known is probably the hydroformylation ( 0x0 reaction ) of alkenes. Depending on reaction conditions, notably CO H2 ratio and temperature, the products are aldehydes (eq 1) or alcohols ( hydroalkylation ) (eq 2). 

On the basis of previous results, the Rueping group started to study alkylations with activated alkenes and nucleophiles other than arenes. Recently, Lewis- and Brpnsted-acid-catalyzed hydroalkylation procedures with 1,3-dicarbonyl compounds as nucleophiles have been developed [69, 70]. These reactions primarily utilized Pd... 

Several examples of gold-catalyzed addition reactions of carbon nucleophiles to unactivated alkenes have been reported in recent years. Yao and Li obtained adducts with high regioselectivity from 3-diketones and various alkenes (styrene derivatives, conjugated dienes, enol ethers) in the presence of cationic gold species prepared in situ from AuCls and AgOTf (Scheme 4-15). This hydroalkylation is... 

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