Article
Chemistry, Organic
Qiongwen Kang, Mengdan Wang, Zongkang Wang, Lu Cheng, Yilin Zhu, Chengyu Wang, Yanzhong Li
Summary: A base-promoted selective C2-N1 ring-expansion reaction of indolones toward substituted quinolines under mild conditions has been developed, achieving the cleavage of one C-N bond and three C-C bonds, and the formation of one C-N and three C-C bonds in one step. This is the first example of a transition-metal free ring-expansion reaction of indolones via the selective insertion of alkynoates into the C2-N1 bond.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Yingming Ren, Yaxin Ge, Qinqin Yan, Shiliu Chen, Yang Li, Lijun Li, Zhong-Quan Liu, Zejiang Li
Summary: The study explores a free radical-initiated cascade cyclization of unactivated alkenes with chloralkanes, providing a protocol for the synthesis of chlorinated heterocycles or polycyclic compounds through selective activation of the alpha-C(sp(3))-H bond of chloralkanes. Various radical inhibition experiments, radical capture operations, and radical clock tests were conducted in this system.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yan He, Qimeng Liu, Tian Gong, Yunfei Liu, Xinying Zhang, Xuesen Fan
Summary: A convenient synthesis protocol for alpha-substituted-beta-oxo azaheterocycles has been developed using oxoammonium salt-promoted cascade reaction. Nucleophiles such as acetyl or cyano group-containing active methylene compounds or morpholines were reacted with saturated cyclic amines, leading to the formation of different intermediates. The chemoselectivity of these reactions was investigated through experimental studies and DFT calculations.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Nuan Chen, Ting Zhou, Hong Zhang, Yuqi Zhu, Ming Lang, Jian Wang, Shiyong Peng
Summary: An unprecedented copper-catalyzed tandem reaction of 1,6-enynes with diazo compounds via a cross-coupling/[2 + 2] cycloaddition sequence was reported, leading to the synthesis of a library of methylenecyclobutane-fused ring systems with high proximal-regioselectivity and diastereoselectivity. Moreover, the key intermediate of 1,6-allenene proceeds via a thermally promoted [2 + 2] cycloaddition in the absence of copper catalyst.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Zheng Liu, Youkun Wang, Jianfeng Huo, Xiao-Jun Li, Shengnan Li, Xiaoning Song
Summary: A new synthetic method was developed for the synthesis of fully substituted isothiazolones using water-mediated reaction conditions, which showed good functional group tolerance, mild reaction conditions, and operational simplicity, providing a potential pathway for applications in pharmaceutical chemistry.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Renhua Zheng, Xiurong Hu, Huajiang Jiang, Haichang Guo, Lei Wang
Summary: A novel and efficient visible-light-induced method has been developed for the one-pot synthesis of functionalized 2-aminothiazoles from easily accessible active methylene ketone derivatives and different thioureas at room temperature. The mild reaction conditions, green chemistry, straightforward work-up, and high yields of the products make this procedure useful for the construction of 2-aminothiazole derivatives.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Jinbiao Ying, Ting Liu, Yunyun Liu, Jie-Ping Wan
Summary: A practical method for the synthesis of 2,2-difluorinated 2,3-dihydrofurans has been developed using enaminones and BrCF2CO2Et as starting materials with Na2CO3 as the catalyst. This method does not require any transition metal reagent and enables the annulative difluoromethylation by partial cleavage of the C=C double bond. Furthermore, treatment with hydrochloric acid in the same reaction system leads to the formation of beta-keto enoic acids via formal enaminone C-N carboxylation.
Article
Chemistry, Multidisciplinary
Feng Pan, Haohu Li, Xiaohua Wang, Liwen Luo, Yanfei Lin, Qingkai Yu, Wenlin Xie, Lianpeng Zhang
Summary: A general and convenient protocol for the visible light-promoted radical-mediated cascade spiro-cyclization/Michael addition of N-arylpropiolamides with thiophenols was developed. This method employs commercially available hydrochloric acid as a cheap promoter and air as a sustainable oxidant. The reaction conditions are tolerant towards many functional groups and produce sulfur-containing benzo[b]pyrrolo[2,1-c][1,4]oxazine-3,9-diones.
Article
Chemistry, Organic
Meng-Jie Jiao, Qiang Hu, Xiu-Qin Hu, Peng-Fei Xu
Summary: A visible-light-driven multistep tandem reaction has been developed for the synthesis of tetralone derivatives from vinyl azides and alkyl bromides under mild conditions, with the potential for easy scalability and high yields. Various 1-tetralone derivatives have been successfully synthesized and converted into desired products with good to high yields.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Austin D. Marchese, Andrew G. Durant, Cian M. Reid, Clara Jans, Ramon Arora, Mark Lautens
Summary: A Pd(0)/blue light catalyzed carboiodination reaction has been reported, which generates a variety of iodinated hetero- and carbocycles. The reaction system is simple and stable, and shows good tolerance towards sensitive functional groups, delivering products in high yields. Experimental evidence supports the reversible C-I bond formation via a single electron mechanism.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Jianbin Li, Amardeep Kumar, Jared C. Lewis
Summary: Despite the unique reactivity of vitamin B(12) and its derivatives, B-12-dependent enzymes remain underutilized in biocatalysis. In this study, the B-12-dependent transcription factor CarH was repurposed to enable non-native radical cyclization reactions. The engineered variant CarH* catalyzes the formation of gamma- and delta-lactams through either redox-neutral or reductive ring closure, showing marked enhancement of reactivity and selectivity compared to the free B-12 cofactor. CarH* also catalyzes an unusual spirocyclization by dearomatization of pendant arenes, producing bicyclic 1,3-diene products instead of the 1,4-dienes provided by existing methods. These results and mechanistic studies highlight the importance of protein scaffolds in controlling B-12 reactivity and expanding the synthetic utility of B-12-dependent enzymes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Applied
Bo Chen, Chang-Sheng Kuai, Jian-Xing Xu, Xiao-Feng Wu
Summary: A Mn(III)-promoted double carbonylation reaction using anilines and alkylborates or Hantzsch esters has been developed for the synthesis of alkyl alpha-ketoamides with excellent selectivity. The method provides a broad range of derivatives in moderate to good yields.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Bin Sun, Xiaohui Zhuang, Jieli Yin, Kesheng Zhang, Haiyun Zhao, Can Jin
Summary: In this study, a photoredox-catalyzed radical cascade reaction was developed for the efficient synthesis of 4-hydroxyalkyl-3,3-difluoro-gamma-lactams. The reaction demonstrated good tolerance towards various functional groups, required lower photocatalyst loading, and was easy to perform.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Polymer Science
Bowen Zhao, Jiajia Li, Xiangqiang Pan, Zhengbiao Zhang, Guoqing Jin, Jian Zhu
Summary: A photoinduced polymerization technique is reported in this study, which can achieve controlled molecular weights and narrow dispersity of polymers at different wavelengths, and can also be used for producing 3D printed objects of varying thicknesses utilizing stereolithography.
Article
Chemistry, Organic
Yingming Ren, Qinqin Yan, Yang Li, Yongjun Gao, Jincan Zhao, Lijun Li, Zhong-Quan Liu, Zejiang Li
Summary: This study presents a persulfate-promoted reaction system for the synthesis of SCF3-substituted dibenzazepines or dioxodibenzothiazepines through the reaction of aryl acetylenes with AgSCF3. The final products were confirmed by single-crystal X-ray diffraction data. The reaction system was further explored through scaled-up experiments, additional transformations, and radical inhibition experiments.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
