Brønsted Acid Catalyzed Addition of Phenols, Carboxylic Acids, and Tosylamides to Simple Olefins

Li, Zigang; Zhang, Junliang; Brouwer, Chad; Yang, Cai‐Guang; Reich, Nicholas W.; He, Chuan

doi:10.1021/ol0610035

Cited by 248 publications

(108 citation statements)

References 46 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Outlook 85 The addition of non-nucleophilic amines to unactivated alkenes converts bulk material into valuable fine chemicals (amines, amides, sulfonamies and carbamate); not only does this confer much added-value to the process, it does so with great atom-economy, satisfying numerous criteria of a green 5 chemical process. 38 To date, several metal complexes have been reported to be catalytically active for these reactions under mild reaction conditions.…”

Section: Scheme 8 Enantioselective Hydroamination Of Unactivated Alkementioning

confidence: 99%

Hydroamination reactions by metal triflates: Brønsted acid vs. metal catalysis?

2010

View full text Add to dashboard Cite

Catalytic hydroamination reactions involving the addition of carboxamide, carbamates and sulfonamides to unactivated C=C bonds are briefly reviewed. Development in this field of catalytic research is briefly charted, followed by a discussion of possible mechanisms, including arguments to support the operation of both metal and Brønsted acid catalysis in these systems. Future developments in the area are summarised.

show abstract

Section: Scheme 8 Enantioselective Hydroamination Of Unactivated Alkementioning

confidence: 99%

Hydroamination reactions by metal triflates: Brønsted acid vs. metal catalysis?

2010

View full text Add to dashboard Cite

show abstract

“…(45)]. [130] Suitable Scheme 18. Proposed mechanism for the ring-expansion of methylenecyclopropanes.…”

Section: Acid-catalyzed Additions To Alkenesmentioning

confidence: 99%

Electrophilic Activation of Alkenes by Platinum(II): So Much More Than a Slow Version of Palladium(II)

2007

View full text Add to dashboard Cite

The electrophilic activation of alkenes by transition-metal catalysts is a fundamental step in a rapidly growing number of catalytic processes. Although palladium is the best known metal for this purpose, the special properties of its third-row cousin platinum (strong metal-ligand bonds and slow substitution kinetics) have enabled the development of transformations that are initiated by addition to the C=C bonds by protic carbon, nitrogen, oxygen, and phosphorus nucleophiles, as well as alkene or arene nucleophiles. Additionally, reactivity profiles, which are often unique to platinum, provide wholly new reaction products. This Review concerns platinum-catalyzed electrophilic alkene activation reactions, with a special emphasis on the mechanistic properties of known systems, on the differences between platinum and palladium catalysts, and on the prospects for the development of new systems.

show abstract

“…When 1-(4-methoxyphenyl)ethanol was used as the substrate, its reaction with 1a gave very low yield, probably because the methoxyl substitution on aromatic systems is unstable under strong Brønsted acid conditions. 20 The reactions of 1a with 1-(2-naphthyl)ethanol (2e) and benzhydrol 2f proceeded smoothly to generate the products 3e and 3f in excellent yields (Table 2, Entries 5, 6). When the allylic alcohol 2g was applied to the reaction with 1a, the allylation product 3g was generated in 70% yield (Table 2, Entry 7).…”

Section: Resultsmentioning

confidence: 99%