Article
Chemistry, Multidisciplinary
Ji-Jia Zhou, Ya-Nan Meng, Li-Gao Liu, Yi-Xi Liu, Zhou Xu, Xin Lu, Bo Zhou, Long-Wu Ye
Summary: The functionalization of etheric C-O bonds via C-O bond cleavage is a promising method for the synthesis of C-C and C-X bonds. However, the enantioselective version of these reactions, mainly involving C(sp(3))-O bond cleavage, is highly challenging. Here, we present a copper-catalyzed asymmetric cascade cyclization, which allows for the efficient and enantioselective synthesis of chromeno[3,4-c]pyrroles with a triaryl oxa-quaternary carbon stereocenter. Notably, this protocol represents the first example of [1,2]-Stevens-type rearrangement via C(sp(2))-O bond cleavage and [1,2]-aryl migration reactions via vinyl cations.
Article
Chemistry, Organic
Shuling Yu, Chao Hong, Zhanxiang Liu, Yuhong Zhang
Summary: In this study, the efficient synthesis of pyranones was achieved through a three-component cascade reaction under ruthenium catalysis using readily available acrylic acids, ethyl glyoxylate, and p-toluenesulfonamide. For the first time, the nucleophilic addition of the vinylic C-H bond of acrylic acids across aldehyde was achieved, followed by intramolecular cyclization and subsequent second insertion to aldehyde to form substituted butenolides. The sulfonamides were eliminated at higher temperature to yield the pyranones.
Article
Chemistry, Multidisciplinary
Yuanyuan Ping, Xiao Li, Qi Pan, Wangqing Kong
Summary: Ligand-directed divergent synthesis is a strategy that can transform common starting materials into distinct molecular scaffolds. This strategy enables the rapid construction of structurally rich collection of small molecules for biological evaluation and reveals novel modes of catalytic transformation, representing one of the most sought-after challenges in synthetic chemistry.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Mingshuai Zhang, Zhuoyuan Liu, Longkun Chen, Donghan Liu, Yulin Sun, Zhangmengjie Chai, Xue-Bing Chen, Fuchao Yu
Summary: A silver-catalyzed protocol for the synthesis of 3-(1H-isochromen)-chromones is described, which shows excellent regioselectivity and high bond-forming efficiency.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Xing Chen, Mengke Li, Zhipeng Liu, Can Yang, Haisheng Xie, Xinwei Hu, Shi-Jian Su, Huanfeng Jiang, Wei Zeng
Summary: An unprecedented Pd/Rh cooperatively catalyzed arylalkynylation of alkynylsilanes was developed to merge an alkynylidene moiety with benzosilacycle, resulting in silaarenes with aggregation-induced emission behavior. Mechanistic investigations revealed that the relay trimetallic transmetalation plays a pivotal role in governing this transformation.
Article
Chemistry, Organic
Shaofeng Li, Hanyu Nie, Mengyan Duan, Wenfei Wang, Congjun Zhu, Chuanjun Song
Summary: This work presents a strategy for the one-pot synthesis of protoberberine alkaloid derivatives using palladium catalyzed cascade alpha-arylation and cyclization, resulting in moderate to excellent isolated yields. The protocol provides an efficient and convenient path to multisubstituted protoberberine derivatives and can directly yield natural alkaloids.
Article
Chemistry, Multidisciplinary
Yao Ge, Fei Ye, Ji Yang, Anke Spannenberg, Haijun Jiao, Ralf Jackstell, Matthias Beller
Summary: A novel palladium-catalyzed cascade carbonylation is described for the direct and selective synthesis of alpha,beta-unsaturated piperidones, generating a broad range of intriguing heterocycles from easily available propargylic alcohols and aliphatic amines. The success of this transformation hinges on the catalytic cleavage of the carbon-carbon triple bond by a specific catalyst with 2-diphenylphosphinopyridine as ligand and suitable reaction conditions, with mechanistic studies pointing to the importance of branched unsaturated acid 11 as a crucial intermediate.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Yongbo Tan, Huawen Huang
Summary: Herein, we present a photocatalyst- and additive-free method for the synthesis of valuable 3,3-disubstituted oxindoles bearing trifluoromethyl alcohol moieties. This method utilizes readily available acrylamides and cheap trifluoropyruvates, and shows broad functional group tolerance and moderate to good yields.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Ping Wu, Liandi Wang, Kaikai Wu, Zhengkun Yu
Summary: This study addresses the challenge of the direct synthesis of triazole 2-oxides in the field of N-heterocyclic chemistry. By utilizing a novel copper-catalyzed nitrosylation/annulation cascade of enaminones and using noncorrosive tert-butyl nitrite, the synthesis of 1H-1,2,3-triazole 2-oxides with wide substrate scopes and good tolerance to various functional groups is achieved.
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, Physical
Houng Kang, Christopher Uyeda
Summary: The (pybox)Ni catalyst enables the reductive cyclization of beta-hydroxy 1,1-dichloroalkenes to form 2,3-dihydrofurans, providing a convenient method for the synthesis of stereochemically complex products. Chiral substrates can be accessed in highly enantioenriched form, with mechanistic studies supporting a vinylidene O-H insertion pathway.
Article
Chemistry, Organic
Weiwei Gao, Xiaodong Wang, Linbin Yao, Bencan Tang, Guohao Mu, Tao Shi, Zhen Wang
Summary: An isomer of lycoplanine A was synthesized with a unique tetracyclic skeleton, and detailed DFT calculations were conducted to explain the selectivity in the reaction. This study may provide valuable experience for the total synthesis of lycoplanine A and other alkaloids with similar spiro-N,O-acetal cores.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Swagata Baruah, Sabera Sultana, Pratiksha Bhorali, Pallabi Saikia, Sanjib Gogoi
Summary: A novel Ru(ii)-catalyzed decarbonylative annulation and direct C-H functionalization reaction of phthalic anhydrides with acrylates is reported, providing an efficient route for the synthesis of 3,7-disubstituted phthalides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yulin Sun, Zhangmengjie Chai, Donghan Liu, Mingshuai Zhang, Longkun Chen, Zhuoyuan Liu, Yongchao Wang, Fuchao Yu
Summary: A Cu-catalyzed oxidative [1+2+1+2] cascade cyclization for the synthesis of 1,4-DHPs was developed using benzylamines as the C4 source. A wide range of N,N-dimethyl enaminones and benzylamines were smoothly employed to provide diverse 1,4-DHPs with high efficiency. This method utilizes a one-pot cascade C(sp(3))-H bond functionalization/C(sp(3))-N cleavage/cyclization strategy to simultaneously form two C(sp(3))-C(sp(2)) bonds, two C(sp(2))-N bonds, and a 1,4-DHP ring.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Mishra Deepak Hareram, Albara A. M. A. El Gehani, James Harnedy, Alex C. Seastram, Andrew C. Jones, Matthew Burns, Thomas Wirth, Duncan L. Browne, Louis C. Morrill
Summary: A new electrochemical method for the generation of alkoxy radicals from alcohols using proton-coupled electron transfer (PCET) approach has been reported. The method allows the functionalization of cycloalkanols and access to a broad range of synthetically useful distally functionalized ketones. The products can be orthogonally derivatized through chemoselective transformations. The electrochemical process has been successfully performed on a gram scale in continuous single-pass flow.
