32094-37-4Relevant academic research and scientific papers
Visible-light-mediated alkylation of 4-alkyl-1,4-dihydropyridines with alkenyl sulfones
Dong, Jianyang,Liu, Yuxiu,Wang, Qingmin,Yue, Fuyang
, p. 8924 - 8928 (2021/11/04)
Herein we report a mild, general protocol for visible-light-mediated alkylation of 4-alkyl-1,4-dihydropyridines with alkenyl sulfones. The protocol permits efficient functionalization of sulfones with a broad range of cyclic and acyclic secondary and tert
Dealkenylative Alkenylation: Formal σ-Bond Metathesis of Olefins
Kwon, Ohyun,Sadykhov, Gusein,Swain, Manisha,Wang, Ruoxi
supporting information, p. 17565 - 17571 (2020/09/01)
The dealkenylative alkenylation of alkene C(sp3)?C(sp2) bonds has been an unexplored area for C?C bond formation. Herein 64 examples of β-alkylated styrene derivatives, synthesized through the reactions of readily accessible feedstock olefins with β-nitrostyrenes by ozone/FeII-mediated radical substitutions, are reported. These reactions proceed with good efficiencies and high stereoselectivities under mild reaction conditions and tolerate an array of functional groups. Also demonstrated is the applicability of the strategy through several synthetic transformations of the products, as well as the syntheses of the natural product iso-moracin and the drug (E)-metanicotine.
RETRACTED ARTICLE: Copper-Catalyzed Decarboxylative C(sp2)-C(sp3) and C(sp)-C(sp3) Coupling of Substituted Cinnamic Acids and 3-Phenyl Propiolic Acid with N-Tosyl Oxaziridines
Nguyen, Bich-Ngoc,Cao, Hai-Thuong
supporting information, p. 5912 - 5915 (2019/08/07)
A mild and efficient strategy for decarboxylative C(sp2)-C(sp3) and C(sp)-C(sp3) coupling of α,β-unsaturated carboxylic acids such as substituted cinnamic acids and 3-phenyl propiolic acid with N-Tosyl oxaziridines was developed. The corresponding products were achieved in moderate to good yields with excellent stereoselectivity. Base-free and oxidant-free conditions allow good functional group tolerance. Radical inhibitors such as TEMPO and BHT completely suppressed the reactions suggesting a radical mechanism was involved. This study is supposed to broaden the frontier of oxaziridines' chemistry and to open up a novel cascade for alkylating reagents.
Copper- and Nickel-Catalyzed Cross-Coupling Reaction of Monofluoroalkenes with Tertiary, Secondary, and Primary Alkyl and Aryl Grignard Reagents
Shi, Hongyan,Dai, Wenpeng,Wang, Biyun,Cao, Song
supporting information, p. 459 - 463 (2018/02/17)
A highly efficient cross-coupling reaction of monofluoroalkenes with tertiary, secondary, and primary alkyl and aryl Grignard reagents in the presence of a catalytic amount of copper or nickel catalyst, respectively, has been developed. The reactions proceeded smoothly at room temperature, providing (E)-alkene isomers in moderate to high yields. Plausible mechanisms of the Ni-catalyzed coupling reaction of monofluoroalkene with Grignard reagents are suggested.
Metal-Free Oxidative Decarbonylative Hydroalkylation of Alkynes with Secondary and Tertiary Alkyl Aldehydes
Ouyang, Xuan-Hui,Song, Ren-Jie,Liu, Bang,Li, Jin-Heng
, p. 1903 - 1909 (2016/07/06)
A new, metal-free, radical-mediated oxidative decarbonylative hydroalkylation of various alkynes with secondary and tertiary alkyl aldehydes using di-tert-butyl peroxide (DTBP) as oxidant is presented. This method enables the simultaneous formation of a C C bond and a C H bond through a sequence of decarbonylation, radical addition and protonation, and provides a straightforward route for transforming alkynes into alkenes with high compatibility with both alkynes and alkyl aldehydes. (Figure presented.) .
Role of sterically demanding chiral dirhodium catalysts in site-selective C-H functionalization of activated primary C-H bonds
Qin, Changming,Davies, Huw M. L.
supporting information, p. 9792 - 9796 (2014/07/22)
The influence of sterically demanding dirhodium tetracarboxylate catalysts on the site selectivity of C-H functionalization by means of rhodium carbene-induced C-H insertion is described. The established dirhodium tetraprolinate-catalyzed reactions of aryldiazoacetates cause preferential C-H functionalization of secondary C-H bonds as a result of competing steric and electronic effects. The sterically more demanding dirhodium tetrakis(triarylcyclopropanecarboxylate) catalysts, exemplified by dirhodium tetrakis[(R)-(1-(biphenyl)-2,2-diphenylcyclopropanecarboxylate)] [Rh 2(R-BPCP)4], favor C-H functionalization of activated primary C-H bonds. Highly site-selective and enantioselective C-H functionalization of a variety of simple substrates containing primary benzylic, allylic, and methoxy C-H bonds was achieved with this catalyst. The utility of this approach has been demonstrated by the late-stage primary C-H functionalization of (-)-∝-cedrene and a steroid.
Lithium hydroxide as base in the Wittig reaction. A simple method for olefin synthesis
Antonioletti,Bonadies,Ciammaichella,Viglianti
, p. 4644 - 4648 (2008/09/20)
A mild and practical procedure for the Wittig olefination, promoted by lithium hydroxide and triphenylbenzyl phosphonium bromide, has been set up for the synthesis of stilbenes and styrenes. The experimental conditions allow aromatic, heteroaromatic, unsaturated and saturated aliphatic aldehydes to give final products in good yields.
NiCl2(dppe)-Catalyzed Geminal Dialkylation of Dithioacetals and Trimethylation of Ortho Thioesters
Tzeng, Yih-Ling,Yang, Ping-Fan,Mei, Nai-Wen,Yuan, Tien-Min,Yu, Chun-Chi,Luh, Tien-Yau
, p. 5289 - 5293 (2007/10/02)
NiCl2(dppe)-catalyzed cross-coupling of cinnamaldehyde dithioacetals gave the corresponding geminal dimethylation products in excellent yields.Allylic ortho thioesters afforded regioselectively the corresponding trimethylation products.The reaction may occur via an 18-electron ?-allyl intermediate, which undergoes facile reductive elimination to afford the geminal dimethylation product.Benzylic dithioacetals having an ortho amino group gave 2-isopropylanilines exclusively.The reaction of benzylic dithioacetals with EtMgBr under the same conditions yielded geminal diethylation products.
Nickel-Catalyzed Geminal Dimethylation of Allylic Dithioacetals
Yang, Ping-Fan,Ni, Zhi-Jie,Luh, Tien-Yau
, p. 2261 - 2262 (2007/10/02)
A geminal dimethyl group is introduced regioselectively in excellent yield from the reactions of allylic dithioacetals and methylmagnesium iodide in the presence of 3 mol percent of NiCl2(dppe) in refluxing ether-benzene.
