65739-09-5Relevant academic research and scientific papers
A Photoredox Coupling Reaction of Benzylboronic Esters and Carbonyl Compounds in Batch and Flow
Chen, Yiding,May, Oliver,Blakemore, David C.,Ley, Steven V.
supporting information, p. 6140 - 6144 (2019/08/26)
Mild cross-coupling reaction between benzylboronic esters with carbonyl compounds and some imines was achieved under visible-light-induced iridium-catalyzed photoredox conditions. Functional group tolerance was demonstrated by 51 examples, including 13 he
Iron-Catalyzed Nucleophilic Addition Reaction of Organic Carbanion Equivalents via Hydrazones
Li, Chen-Chen,Dai, Xi-Jie,Wang, Haining,Zhu, Dianhu,Gao, Jian,Li, Chao-Jun
, p. 3801 - 3805 (2018/07/25)
Earth-abundant and well-defined iron complexes are found to be cheap and effective catalysts for a series of "umpolung" nucleophilic additions of hydrazones. The new catalytic system not only maintains the broad substrate scope of an earlier expensive ruthenium system but also attains chemoselectivity of different kinds of carbonyl groups. Furthermore, the iron catalyst enables this reaction at ambient temperature.
Aldehydes as alkyl carbanion equivalents for additions to carbonyl compounds
Wang, Haining,Dai, Xi-Jie,Li, Chao-Jun
, p. 374 - 378 (2017/04/03)
Nucleophilic addition reactions of organometallic reagents to carbonyl compounds for carbon-carbon bond construction have played a pivotal role in modern chemistry. However, this reaction's reliance on petroleum-derived chemical feedstocks and a stoichiometric quantity of metal have prompted the development of many carbanion equivalents and catalytic metal alternatives. Here, we show that naturally occurring carbonyls can be used as latent alkyl carbanion equivalents for additions to carbonyl compounds, via reductive polarity reversal. Such 'umpolung' reactivity is facilitated by a ruthenium catalyst and diphosphine ligand under mild conditions, delivering synthetically valuable secondary and tertiary alcohols in up to 98% yield. The unique chemoselectivity exhibited by carbonyl-derived carbanion equivalents is demonstrated by their tolerance to protic reaction media and good functional group compatibility. Enantioenriched tertiary alcohols can also be accessed with the aid of chiral ligands, albeit with moderate stereocontrol. Such carbonyl-derived carbanion equivalents are anticipated to find broad utility in chemical bond formation.
A mild oxidative aryl radical addition into alkenes by aerobic oxidation of arylhydrazines
Taniguchi, Tsuyoshi,Zaimoku, Hisaaki,Ishibashi, Hiroyuki
, p. 4307 - 4312 (2011/05/07)
A mild and practical oxyarylation of alkenes by oxidative radical addition has been developed by using aerobic oxidation of hydrazine compounds. The use of a catalytic amount of potassium ferrocyanide trihydrate (K4[Fe(CN) 6]·3 H2O) and water accelerated this radical reaction to give peroxides or alcohols from simple alkenes in good yields. The environmentally friendly and economical radical reactions were achieved at room temperature in the presence of iron catalyst, oxygen gas, and water. A method involving aniline as a radical precursor is also described. Copyright
