- Synthesis of α-Alkylated Ketones via Selective Epoxide Opening/Alkylation Reactions with Primary Alcohols
-
A new method for converting terminal epoxides and primary alcohols into α-alkylated ketones under borrowing hydrogen conditions is reported. The procedure involves a one-pot epoxide ring opening and alkylation via primary alcohols in the presence of an N-heterocyclic carbene iridium(I) catalyst, under aerobic conditions, with water as the side product.
- Gen?, Serta?,Gülcemal, Süleyman,Günnaz, Salih,?etinkaya, Bekir,Gülcemal, Derya
-
supporting information
p. 5229 - 5234
(2021/07/19)
-
- Visible-Light-Promoted Photocatalyst-Free Hydroacylation and Diacylation of Alkenes Tuned by NiCl2·DME
-
Herein, we describe a visible light-promoted hydroacylation strategy that facilitates the preparation of ketones from alkenes and 4-acyl-1,4-dihydropyridines via an acyl radical addition and hydrogen atom transfer pathway under photocatalyst-free conditions. The efficiency was highlighted by wide substrate scope, good to high yields, successful scale-up experiments, and expedient preparation of highly functionalized ketone derivatives. In addition, this protocol allows for the synthesis of 1,4-dicarbonyl compounds through alkene diacylation in the presence of NiCl2·DME.
- Zhao, Xinxin,Li, Bing,Xia, Wujiong
-
p. 1056 - 1061
(2020/02/15)
-
- Switchable Chemoselective Transfer Hydrogenations of Unsaturated Carbonyls Using Copper(I) N-Donor Thiolate Clusters
-
Unsaturated alcohols and saturated carbonyls are important chemical, pharmaceutical, and biochemical intermediates. We herein report an efficient transfer hydrogenation protocol in which conversion of unsaturated carbonyl compounds to either unsaturated alcohols or saturated carbonyls was catalyzed by Cu(I) N-donor thiolate clusters along with changing hydrogen source (isopropanol or butanol) and base (NaOH or K2CO3). Mechanistic studies supported by DFT transition state modeling indicate that such a chemoselectivity can be explained by the relative concentrations of Cu(I) monohydride and protonated Cu(I) hydride complexes in each catalytic system.
- Zhang, Meng-Juan,Tan, Da-Wei,Li, Hong-Xi,Young, David James,Wang, Hui-Fang,Li, Hai-Yan,Lang, Jian-Ping
-
p. 1204 - 1215
(2018/02/09)
-
- Iridium(I)-Catalyzed Alkylation Reactions to Form α-Alkylated Ketones
-
A highly effective and green procedure for the formation of α-alkylated ketones has been disclosed via the reaction of primary alcohols with secondary alcohols and ketones by using [IrCl(COD)(NHC)] complexes as a catalyst. Various α-alkylated ketones were obtained in high yields from the alkylation of alcohol with alcohol and ketone with alcohol through a borrowing hydrogen reaction by using 0.05-0.5 mol % iridium(I) and a catalytic amount of KOH (5-10 mol %) as the base under air atmosphere and within very short reaction times.
- Gen?, Serta?,Günnaz, Salih,?etinkaya, Bekir,Gülcemal, Süleyman,Gülcemal, Derya
-
p. 2875 - 2881
(2018/03/09)
-
- Transition-Metal-Free Synthesis of Homo- and Hetero-1,2,4-Triaryl Benzenes by an Unexpected Base-Promoted Dearylative Pathway
-
An unprecedented approach for the synthesis of homo- and hetero-1,2,4-triaryl benzenes has been developed using a simple base-mediated reaction of either α-aryl cinnamyl alcohols or α,γ-di-aryl propanones. The salient feature of this strategy involves the sequential hydride transfer, regiospecific condensation, regiospecific dearylation, and aromatization under metal-free reaction conditions. The synthesis of unsymmetrically substituted triphenylenes by oxidative coupling of the synthesized 1,2,4-triaryl benzenes has also been demonstrated.
- Rehan, Mohammad,Maity, Sanjay,Morya, Lalit Kumar,Pal, Kaushik,Ghorai, Prasanta
-
p. 7728 - 7732
(2016/07/07)
-
- Long-Range Triplet Hydrogen Abstraction. Photochemical Formation of 2-Tetralols from β-Arylpropiophenones
-
The four ketones β-(o-tolyl)- and β-mesitylpropiophenone and -isobutyrophenone all undergo photocyclization to 2-tetralols via triplet-state ε-hydrogen abstraction.The intermediate 1,6-biradicals cyclize in 100percent efficiency.The triplets react in very
- Zhou, Boli,Wagner, Peter J.
-
p. 6796 - 6799
(2007/10/02)
-