Article
Chemistry, Multidisciplinary
Qiqige Qiqige, Rylan J. Lundgren, Duanyang Kong
Summary: Stereodivergent dual catalysis is a powerful tool for selectively preparing four stereoisomers from molecules with two chiral centers. However, generating molecules with three newly formed stereocenters using dual catalyst approaches remains challenging.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Liansheng Liu, Yiying Liu, Shan Li, Jin Gao, Jing Li, Junfa Wei
Summary: The Rh(III)-catalyzed synthesis of benzoisothiazole spiropyrrolidinediones using sulfoximine as a directing group and maleimides as a coupling partner under a C-H activation and [4 + 1] annulation strategy is described. The cyclization reaction is compatible with various substituted sulfoximine and maleimides. Deuterium-labeling studies were conducted to investigate the mechanism of the reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Wei Hu, Chao Pi, Di Hu, Xiliang Han, Yangjie Wu, Xiuling Cui
Summary: A rhodium-catalyzed cyclization of azobenzenes and vinylene carbonate has been developed to construct indazolo[2,3-a]quinolines. This method offers high yields and broad functional group tolerance, forming three C-C bonds and one C-N bond in one pot. Additionally, the resulting products exhibit favorable fluorescence properties.
Article
Chemistry, Organic
Ying-Ti Huang, Indrajeet J. Barve, Yi-Ting Huang, Sandip Dhole, Wei-Jung Chiu, Chung-Ming Sun
Summary: A Rh(III)-catalyzed cascade C-H activation and cyclization reaction was reported for the synthesis of benzimidazole-fused isoquinolines and benzimidazole-spiro isoindoles. Selective formation of these products can be achieved by using unsubstituted and substituted benzimidazoles at different positions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Naohiro Hirako, Takeshi Yasui, Yoshihiko Yamamoto
Summary: 3,4-Fused 2-quinolone frameworks play important roles in natural products and biologically active compounds. Rh(III)-catalyzed alkenyl C-H functionalization of 4-amino-2-quinolones provides an efficient and selective approach to access these structural motifs.
Article
Chemistry, Organic
Yinsong Wu, Xinwei He, Mengqing Xie, Ruxue Li, Yi Ning, Jiahui Duan, Enshen Zhang, Yongjia Shang
Summary: The Rh(III)-catalyzed cascade nucleophilic addition/intramolecular annulation of 2-diazo-1,3-diketones with 1,3-dicarbonyl compounds has been successfully achieved to yield 6,7-dihydrobenzofuran-4(5H)-ones in up to 91% yields. The reaction tolerates a wide range of substrates and functional groups under optimized conditions and is scalable and adaptable to late-stage functionalization.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Bingxian Liu, Lingyun Yang, Zhenzhen Dong, Junbiao Chang, Xingwei Li
Summary: The rhodium(III)-catalyzed annulation of 2-biphenylboronic acids with activated alkenes has been achieved, leading to the synthesis of fused or bridged cyclic skeletons via transmetalation-initiated C-H activation. The bulky cyclopentadienyl ligand in the catalyst promoted reductive elimination and led to the formation of [4 + 2] annulated products. The substrate scope was broad, with high yields of up to 99% obtained under air-tolerant conditions.
Article
Chemistry, Organic
Zhidong Jiang, Jianhui Zhou, Haoran Zhu, Hong Liu, Yu Zhou
Summary: A novel Rh(III)-catalyzed C-H activation/annulation cascade of indole-enaminones with diazo compounds was reported, generating diversely functionalized carbazole frameworks with good to excellent yields. The most notable feature is the formation of a novel [5 + 1] cyclization product, accompanied by the complete removal of acetyl and N,N-dimethyl groups from the substrates, rather than the expected [4 + 2] cyclization products.
Article
Chemistry, Organic
Bo Zhu, Huili Sun, Huihui Fan, Mengqi Wang, Fangyuan Guo, Yubing Zhai, Gongming Zhu, Junbiao Chang
Summary: The formation of acyclic azomethine imine 1,3-dipoles is a fundamental strategy for the assembly of chiral pyrazolidines, but precise chemoselective control remains challenging. In this study, a highly enantioselective Bronsted base-catalyzed aza-Michael addition and cascade cycloaddition reactions were reported, which yielded chiral acyclic amination products and chiral pyrazolidines with excellent enantio- and diastereoselectivities. The enantio-enriched aza-Michael addition derivatives can be easily transformed into 2-pyrazolines with trifluoromethyl units, and the selected chiral linear acylhydrazone derivatives showed good biological specificity for the tumor cell line MCF-7.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Yimin Hu, Wangyu Shi, Zhengyang Yan, Jianning Liao, Min Liu, Jiaqing Xu, Wei Wang, Yongjun Wu, Cheng Zhang, Hongchao Guo
Summary: An efficient method using K2CO3 catalysis has been developed for the 1,4-addition/intramolecular cyclization/aromatization reaction of aurone-derived 1-azadienes with trisubstituted allenoates, resulting in a series of benzofuro[3,2-b]pyridines in moderate to excellent yields. The reaction proceeds efficiently under an air atmosphere without the need for transition metal catalysts, providing a concise approach to benzofuro[3,2-b]pyridines.
Article
Chemistry, Organic
Wenwei Li, Honggui Zhou, Yequan He, Ge Zeng, Yumeng Zheng, Yangni Hu, Zhongyan Chen, Jing-Yuan Ge, Ningning Lv, Jiuxi Chen
Summary: We report a novel pathway to synthesize gamma-lactams using acetonitrile analogues as coupling partners. This method does not require oxidants, ligands, and Lewis acids, and exhibits a broad substrate scope, good functional group tolerance, and excellent chemo/stereoselectivity. Scale-up reactions and late-stage derivatizations demonstrate the potential synthetic utility of this methodology.
Article
Chemistry, Applied
Bita Manavi, Hossein Zahedian Tejeneki, Frank Rominger, Mahsa Armaghan, Walter Frank, Hamid Reza Bijanzadeh, Saeed Balalaie
Summary: This report discusses two distinctive intramolecular cyclizations of o-propargyloxy diketopiperazines achieved via a copper(I)-catalyzed reaction, offering an opportunity for the synthesis of challenging Diazabicyclics and Spiro-Diketopiperazinochromanes with high yields and exclusive diastereoselectivity.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Zhenzhen Dong, Pengfei Li, Xingwei Li, Bingxian Liu
Summary: Divergent synthesis of useful skeletons has been achieved through rhodium(III)-catalyzed C-H activation of iminopyridinium ylides and coupling with various unsaturated coupling reagents. The reactions yield isocoumarins, isoquinolones, and fluorinated alkenes with wide substrate scopes and good efficiency under redox-neutral and air-tolerant conditions. Representative products exhibit solid-state fluorescent property and bioactivity of inhibition toward human cancer cells.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Daniel L. Priebbenow, Carol Hua
Summary: Studies on Cp*Rh(iii)-catalyzed hydroarylation of alkenes with aryl acyl silanes revealed a new synthetic strategy to access unique silicon-based indene frameworks and benzofurans. This represents the second example of rhodium-catalyzed C-H functionalization using acyl silanes as directing groups, with intramolecular aldol condensation being the key step in the process.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Huawei Lin, Xianru Yang, Wenyue Ning, Xiaofang Huang, Xiaoqun Cao, Yanqing Ge, Biming Mao, Chang Wang, Hongchao Guo, Chunhao Yuan
Summary: Nitrogen-containing heterocycles play crucial roles in biologically active natural products and pharmaceuticals, and the palladium-catalyzed decarboxylative cycloaddition reactions are powerful synthetic tools. Vinyl benzoxazinones have emerged as versatile building blocks for nitrogenous skeletons.
