58122-02-4Relevant academic research and scientific papers
Synthesis of α-Alkylated Ketones via Selective Epoxide Opening/Alkylation Reactions with Primary Alcohols
Gen?, Serta?,Gülcemal, Süleyman,Günnaz, Salih,?etinkaya, Bekir,Gülcemal, Derya
supporting information, p. 5229 - 5234 (2021/07/19)
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.
Borane-Catalyzed, Chemoselective Reduction and Hydrofunctionalization of Enones Enabled by B-O Transborylation
Nicholson, Kieran,Langer, Thomas,Thomas, Stephen P.
supporting information, p. 2498 - 2504 (2021/04/13)
The use of stoichiometric organoborane reductants in organic synthesis is well established. Here these reagents have been rendered catalytic through an isodesmic B-O/B-H transborylation applied in the borane-catalyzed, chemoselective alkene reduction and formal hydrofunctionalization of enones. The reaction was found to proceed by a 1,4-hydroboration of the enone and B-O/B-H transborylation with HBpin, enabling catalyst turnover. Single-turnover and isotopic labeling experiments supported the proposed mechanism of catalysis with 1,4-hydroboration and B-O/B-H transborylation as key steps.
Visible-Light-Promoted Photocatalyst-Free Hydroacylation and Diacylation of Alkenes Tuned by NiCl2·DME
Zhao, Xinxin,Li, Bing,Xia, Wujiong
, p. 1056 - 1061 (2020/02/15)
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.
Transition-Metal-Free Highly Chemoselective and Stereoselective Reduction with Se/DMF/H2O System
Li, Hong-Chen,An, Cui,Wu, Ge,Li, Guo-Xing,Huang, Xiao-Bo,Gao, Wen-Xia,Ding, Jin-Chang,Zhou, Yun-Bing,Liu, Miao-Chang,Wu, Hua-Yue
supporting information, p. 5573 - 5577 (2018/09/12)
A novel metal-free reduction system, in which H2Se (or HSe-) produced in situ from Se/DMF/H2O acts as the active reducing species, has been developed. By using water as an inexpensive, safe, and environmentally friendly surrogate as the hydrogen donor, this new reduction system incorporating Se/DMF/H2O displayed high selectivity and good activity in the reduction of α,β-unsaturated ketones and alkynes. Therefore, this reduction system has great potential to be a general and practical reduction methodology in organic transformation.
Compounding method for beta-aryl propiophenone compound
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Paragraph 0056-0059, (2018/03/01)
The invention discloses a compounding method for a beta-aryl propiophenone compound. The compounding method is characterized by taking chalcone compounds as reaction substrates, and selectively chemically reducing the carbon-carbon double bonds in the rea
Evaluation of AgPd Nanoshells in Dual Catalysis: One-Pot Silane Oxidation and Reduction of Organic Compounds
Kisukuri, Camila M.,Reis, Jo?o L. M. S.,Rodrigues, Thenner S.,Camargo, Pedro H. C.,Andrade, Leandro H.
, p. 3657 - 3662 (2016/12/14)
AgPd nanoshells (AgPd NSs) were used as dual catalysts for hydrogen production and reduction of organic compounds in a one-pot protocol. AgPd NSs were very efficient catalysts for the reduction of several functional groups, including alkenes, alkynes, imines, nitro compounds, and azides. Excellent chemoselectivities were observed for α,β-unsaturated ketones, esters, and cinnamonitrile. Also, deuterium-labeled compounds were prepared by using D2O instead of H2O. A packed-bed reactor containing the immobilized AgPd NSs in silica (AgPd/SiO2) was designed to be used in continuous-flow conditions. An optimized flow system with AgPd NSs was able to give the desired compounds in high conversions with 30–60 min residence time (tR).
A novel transition metal-free conjugate reduction of α,β-unsaturated ketones with tosylhydrazine as a hydrogen source
Zhou, Xiaomeng,Li, Xiaokang,Zhang, Wei,Chen, Junmin
supporting information, p. 5137 - 5140 (2015/02/19)
A novel and efficient method has been developed for the chemoselective conjugate reduction of α,β-unsaturated ketones with tosylhydrazine as a hydrogen source to the corresponding saturated ketones in moderate to good yields. The present protocol does not require the use of transition metal, and is efficient being applicable to a wide range of substrates (25 examples).
Benzotriazole as a Synthetic Auxiliary: Advantageous Syntheses of Substituted Diarylmethanes and Heterocyclic Analogues
Katritzky, Alan R.,Lan, Xiangfu,Lam, Jamshed N.
, p. 4397 - 4403 (2007/10/02)
4-(Benzotriazol-1-ylmethyl)-N,N-dimethylaniline (1b) can be substituted at the CH2 link via lithiation.Both the parent and substituted derivatives react with a variety of electron-rich benzenoid and heteroaromatic compounds in a novel approach to leuco dy
