Article
Chemistry, Organic
Chuan-Ming Hong, Si-Qi Xiong, Xue Zhang, Kai-Xian Ma, Qing-Hua Li, Tang-Lin Liu
Summary: This paper discloses a silver-catalyzed 1,3-aza-benzyl migration of allyl alcohols by utilizing chelation-assisted selective cleavage of an unstrained C(sp3)-C(sp3) bond. This approach provides an available, efficient, high atom-economic, and environmentally benign procedure, leading to alkylation products with broad substrate scopes and excellent yields. The migration proceeds via a one-pot, two-step process involving a free-state alkyl metal species.
Article
Chemistry, Applied
Tao Yi, Quan Liu, Yue Zhang, Jinhao Huang, Zhigang Zeng, Yunfeng Chen
Summary: A copper-catalyzed cascade reaction was reported for the selective oxidative cleavage of C-C bonds in β-alkyl nitroolefins, followed by oxidative amidation with amines or amides. The reaction showed high selectivity and yielded α-ketoamides with 66-88% yields. Mechanistic studies revealed that the reaction occurred on more electron-rich allylic nitro tautomers originating from the equilibrium of conjugated nitroalkenes.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Review
Chemistry, Organic
Yuan-Ye Jiang, Chao Chen
Summary: This review introduces the advances in computational studies on Cu-catalyzed aerobic reactions, focusing on the cooperation mechanisms of copper catalysts and O2 in dehydrogenation, oxygenation, and coupling reactions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Review
Chemistry, Organic
Yuan-Ye Jiang, Chao Chen
Summary: This review summarizes the advances in computational studies on Cu-catalyzed aerobic reactions and focuses on the cooperation mechanisms of copper complexes and dioxygen.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Alexander Bunnell, Naish Lalloo, Conor Brigham, Melanie S. Sanford
Summary: This report describes a Pd-catalyzed decarbonylative coupling reaction for the synthesis of difluorobenzyl-substituted (hetero)arenes using (hetero)aryl boronate esters. The reaction was found to be highly selective and effective for a range of electronically diverse boronate esters and substituted difluorobenzyl glutarimides.
Article
Chemistry, Applied
Nithin Pootheri, Sunwoo Lee
Summary: A method for preparing 18O-labeled esters through a Ni-catalyzed three-component reaction has been developed. This method exhibits excellent selectivity and compatibility with various amides and alkyl halides, enabling the synthesis of diverse isotopically labeled esters.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Ziwei Zhao, Zhanrong Zhang, Qinglei Meng, Bingfeng Chen, Jinliang Song, Huizhen Liu, Buxing Han
Summary: Effectively cleaving and functionalizing C(OH)-C bonds is crucial for producing valuable chemicals from renewable biomass resources. The inert nature of C(OH)-C bonds and various side reactions associated with hydroxyl groups hinder their oxidative cleavage efficiency and selectivity. Converting secondary alcohols to aldehydes is particularly challenging due to the tendency of over-oxidation. Noble-metal catalysts are necessary to achieve satisfactory aldehyde yields.
Article
Chemistry, Organic
Abhishek A. Kadam, Tanner L. Metz, Colton M. David, Mason T. Koeritz, Levi M. Stanley
Summary: In this study, a novel palladium-catalyzed reaction was disclosed using imides as acyl electrophiles to prepare a series of polycyclic compounds. The reaction achieved moderate to high yields of α,β-unsaturated ketones, which were readily transformed into polycyclic architectures via thermal hetero-Diels-Alder reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Xiao-Hua Zhou, Jun-Hui Zhu, Guang-Ao Song, Xin-Li Jiang, Xiao-Jun Fang, Zheng Xu, Li-Wen Xu
Summary: A palladium-catalyzed cross-coupling silylation reaction has been developed for the synthesis of structurally diverse silanes. This method exhibits simplicity, wide substrate scope, high chemoselectivity, and good tolerance towards functional groups. The study highlights the importance of this reaction in the field of organosilicon chemistry.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Tingting Li, Gerald B. Hammond, Bo Xu
Summary: A widely applicable approach to synthesize ketones, esters, and amides via the oxidative C-C bond cleavage of readily available alkyl aldehydes has been developed using green and abundant molecular oxygen as the oxidant, and base metals (cobalt and copper) as catalysts. This strategy can be extended to the one-pot synthesis of ketones from primary alcohols and alpha-ketoamides from aldehydes.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Shengyun Hu, Huangdi Feng, Hui Xi, Yuchen Meng, Ming Li, Liliang Huang, Junhai Huang
Summary: Transition-metal catalyzed C-N bond activation is a promising method for bond cleavage and formation in organic synthesis. This study demonstrates a time-dependent selective synthesis of propargylamines using the CuBr2/TBHP catalysis system, which allows for site-selective deamination/alkynylation of secondary amines. Control over reaction time is critical for obtaining high yields of the desired products.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Shangzhi Tan, Xiangzhu Yu, Lina Zhu, Weiru Fu, Lianyue Wang
Summary: A heterogeneous iron-based catalyst has been developed for the conversion of alcohols to esters, and it also shows effectiveness in the degradation of organosolv lignin. The catalyst exhibits good recyclability and can be easily reused multiple times without significant loss of catalytic activity.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2022)
Article
Chemistry, Multidisciplinary
Yasuaki Iyori, Rina Ueno, Aoi Morishige, Naoto Chatani
Summary: The Ni-catalyzed reaction involves annulation of ortho-phenoxy-substituted aromatic amides with alkynes to form 1(2H)-isoquinolinones in the presence of (LiOBu)-Bu-t as a base. The reaction proceeds even without a ligand under mild conditions at 40 degrees C. An electron-donating group on the aromatic ring facilitates the reaction, which is also applicable to various leaving groups such as carbamate, methylthio, and cyano.
Article
Chemistry, Multidisciplinary
Kui Zhang, Cong Wei, Yan Li, Yueyang Yao, Liangliang Song, Jia Jin, Lingchao Cai
Summary: A low-cost and commercially available Cu(OAc)(2) catalyzed hydrazination of cyclopropyl alcohols was developed, providing a feasible method for the preparation of hydrazine derivatives. The hydrazine compound could further undergo a one-pot two-step reaction to yield 4,5-dihydropyrazoles. Furthermore, the hydrazine and 4,5-dihydropyrazole core structures showed encouraging antifungal activity.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Chikkabagilu Nagaraju Shambhavi, Masilamani Jeganmohan
Summary: A Ru(II)-catalyzed weak chelating group-aided ortho-C-H alkylation of arylamides with unactivated olefins in a redox-neutral fashion was demonstrated. This reaction was suitable for various substituted arylamides and unactivated aliphatic alkenes, with pivalic acid playing a dual role.
