Article
Chemistry, Organic
Anais Loison, Gilles Hanquet, Fabien Toulgoat, Thierry Billard, Armen Panossian, Frederic R. Leroux
Summary: In this study, we report the in situ generation of a novel intermediate, difluoromethoxylated ketenimines, obtained from the corresponding oxime through a Beckmann rearrangement. The reactivity potential of this intermediate is demonstrated as it easily undergoes addition reactions with various nucleophiles. The broad applicability of this transformation leads to a chemical library of original molecules bearing -OCHF2, an Emergent Fluorinated Group (EFG).
Article
Chemistry, Organic
Rajendra K. Mallick, Srinivas Vangara, Nagarjuna Kommu, Tirumaleswararao Guntreddi, Akhila K. Sahoo
Summary: This paper describes a novel Cu(II)-catalyzed rearrangement reaction for the synthesis of a series of synthetically important α-(m-substituted phenol)-α,β-unsaturated ketones, with a wide scope of functional group tolerance and synthetic viability. The synthesis of α,β-unsaturated ketones is also demonstrated in this study.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Mingchuang Shen, Yingzhang Shi, Zhiwen Wang, Taikang Wu, Ling Hu, Ling Wu
Summary: Ultrathin Bi4Ti3O12 nanosheets with a thickness of about 3.9 nm were successfully synthesized and used as a photocatalyst for the oxidation of benzyl alcohol. The nanosheets exhibited a photocatalytic performance about 8 times higher than that of bulk Bi4Ti3O12. The enhanced performance was attributed to the presence of more surface Lewis acid sites for adsorption and activation of benzyl alcohol, as well as the efficient utilization of photogenerated electrons and holes to produce radicals.
JOURNAL OF COLLOID AND INTERFACE SCIENCE
(2022)
Article
Chemistry, Multidisciplinary
Shintaro Ishida, Kengo Sakamoto, Ryo Kobayashi, Takeaki Iwamoto
Summary: This study reports the reactions of silanone with triarylboranes to form boroxysilanes. Experimental results and computational studies show that the electrophilicity of the unsaturated silicon atom is enhanced by the complexation of silanone with triarylboranes, and subsequent aryl migration from the boron atom to the electrophilic silicon atom takes place.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Physical
Hajime Maeda, Saki Nakamura, Taniyuki Furuyama, Masahito Segi
Summary: The reaction of 1-naphthyl naphthylmethyl ethers 1 and 2 with Lewis acids in CH2Cl2 resulted in rearrangement of the naphthylmethyl group to different positions of the naphthalene ring. The rearrangement of 2-naphthyl ethers 3 and 4 proceeded to the 1-position. Irradiation of compound 1 in benzene solution led to rearrangement at the 4-position, while rearrangement of compound 2 occurred at the 2- and 4-positions. The regioselectivity of the reactions can be explained by charge density, spin density, steric hindrance, and solvent cage effect.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Physical
Pingping Wu, Lei Song, Yue Wang, Xuehua Liu, Zhengke He, Peng Bai, Zifeng Yan
Summary: Enhancing benzaldehyde selectivity and improving oxygen transfer during the reaction can be achieved by generating more surface Lewis acid sites on ZrO2-modified alumina. The introduction of ZrO2 also enhances noble metal dispersion, leading to the formation of more active sites for improved catalytic activity.
APPLIED SURFACE SCIENCE
(2021)
Review
Chemistry, Multidisciplinary
Daniele Fiorito, Simone Scaringi, Clement Mazet
Summary: This review covers the one-pot reactions centered around transition metal-catalyzed isomerization of alkenes, showcasing their advantages in atom, step, and redox economy, as well as the preparation of value-added products that are difficult to access through conventional methods.
CHEMICAL SOCIETY REVIEWS
(2021)
Article
Chemistry, Physical
Sergio Rojas-Buzo, Patricia Concepcion, Avelino Corma, Manuel Moliner, Mercedes Boronat
Summary: Different silicates containing Lewis acid sites were studied for the tandem N-alkylation reaction of aniline with benzyl alcohol, with Hf-Beta and Zr-Beta showing the highest catalytic activity. The N-alkylation reaction was found to proceed through a hydrogen borrowing pathway, with in situ Hf-hydride species generated. Thermal treatment of the catalyst increased the amount of active species, and the Hf-Beta zeolite could be reused multiple times without significant deactivation.
Article
Biochemistry & Molecular Biology
Xiang Yu, Yinkai Xi, Yi Sui, Yang Liu, Guifen Chen, Minjie Zhang, Yan Zhang, Guoyong Luo, Yi Long, Wude Yang
Summary: A hydroxide-mediated SNAr rearrangement was used to synthesize new depside derivatives with diaryl ether skeleton from barbatic acid. The synthesized compounds were characterized using various techniques and screened for cytotoxicity against cancer cell lines. Compound 3b exhibited the highest antiproliferative activity against liver cancer cells and showed low toxicity, suggesting its potential for further investigation.
Article
Chemistry, Applied
Xin Jin, Rusi Peng, Wen Tong, Jinpeng Yin, Hao Xu, Peng Wu
Summary: In the Beckmann rearrangement, TS-1 exhibits superior catalytic performance with silanol groups (including terminal silanols, hydrogen-bonded silanols, and silanol nests) as the active centers. Monolithic TS-1 microspheres (M-TS-1) show higher catalytic activity compared to conventional TS-1, and the diffusion properties of M-TS-1 can be further improved through chemical modifications to achieve longer reaction lifetime.
Article
Chemistry, Applied
Peng Bai, Tao Zhou, Xiaohua Wang, Xiaofei Liu, Yi Wang, Yue Wang, Edgar Muhumuza, Yonghui Zhang, Pingping Wu
Summary: A series of Au-Pd alloy nanoparticles catalysts supported on gamma-Al2O3 were synthesized using MPTMS as an anchoring ligand. The results showed that the catalysts modified with MPTMS exhibited high catalytic activity and benzaldehyde selectivity, which can be attributed to the anchoring and dispersion effect of MPTMS on Au-Pd NPs and the formation of more surface Lewis acid sites.
Article
Plant Sciences
Georgijs Stakanovs, Anastasija Blazevica, Sergey Belyakov, Dace Rasina, Aigars Jirgensons
Summary: This study presents the first semisynthetic routes towards terrestrial anti-inflammatory natural products linariophyllene A-C and the refined route towards marine natural product rumphellolide H. By determining the correct structures of these natural products, the study enriched the diversity of sesquiterpenoids and provided reference standards for further research on the chemical constituents of terrestrial and marine organisms.
JOURNAL OF NATURAL PRODUCTS
(2023)
Article
Chemistry, Multidisciplinary
Jinxiu Xu, Yanji Song, Jia Yang, Bingqian Yang, Zhishan Su, Lili Lin, Xiaoming Feng
Summary: In this article, a highly diastereo- and enantioselective alpha-regioselective Mannich reaction is achieved by using chiral N,N'-dioxide/Sc-III catalysts. A series of chiral alpha-quaternary allyl aldehydes and homoallylic alcohols with vicinal multisubstituted stereocenters are constructed in excellent yields, good diastereomeric ratios, and excellent enantiomeric excess values. Experimental studies and DFT calculations reveal the critical factors for the alpha-regioselectivity to be the large steric hindrance of the ligand and the Boc protecting group of imines.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Tien Tan Bui, Hee-Kwon Kim
Summary: A novel method for direct transformations of benzyl THP ethers and allyl benzyl ethers to azido compounds was developed in this study. The direct nucleophile additions of carbon nucleophiles to these compounds were successfully accomplished in the presence of catalytic AlCl3. This method could be applied to various direct transformations such as azidation, allylation, and alkynylation.
SYNTHETIC COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Qianchi Lin, Sujuan Zheng, Long Chen, Jin Wu, Jinzhao Li, Peizhi Liu, Shunxi Dong, Xiaohua Liu, Qian Peng, Xiaoming Feng
Summary: In this study, a highly enantioselective tandem reaction of alpha-alkynylketoamides with diarylphosphine oxides was achieved, leading to the synthesis of trisubstituted allenes with a diarylphosphinate functionality. The reaction showed broad substrate scope, high regio- and enantioselectivity, and good functional-group compatibility. The synthetic utility of the methodology was demonstrated by the conversion of products into complex bridged polycyclic architectures.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
