Article
Chemistry, Organic
En-He Huang, Ying-Qi Zhang, Da-Qiu Cui, Xin-Qi Zhu, Xiao Li, Long-Wu Ye
Summary: A new copper-catalyzed Si-H bond insertion reaction involving N-propargyl ynamides and hydrosilanes has been discovered, providing an efficient method for the practical and atom-economic synthesis of valuable organosilanes in generally moderate to excellent yields under mild reaction conditions. This reaction also introduces a new pathway for Si-H bond insertion involving vinyl cations as key intermediates.
Article
Chemistry, Organic
Chuan-Chuan Wang, Ya-Li Qu, Xue-Hua Liu, Zhi-Wei Ma, Bo Yang, Zhi-Jing Liu, Xiao-Pei Chen, Ya-Jing Chen
Summary: In this study, the convenient preparation of N2-unprotected five-membered cyclic guanidines was achieved via a cascade [3 + 2] cycloaddition between organo-cyanamides and alpha-haloamides under mild conditions in good to excellent yields (up to 99%). The resulting cyclic guanidines could be easily transformed into hydantoins through hydrolysis.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Bin Li, Jiang-Ling Shi, Ying Xia
Summary: The construction of all-carbon quaternary centers in small-ring systems is an important yet challenging task in organic synthesis. In this study, we developed a practical method for building all-carbon quaternary centers in gem-difluorinated cyclopropanes (DFCs) by utilizing gem-difluorocyclopropyl bromides (DFCBs) as general and versatile building blocks. The reaction involves the participation of a gem-difluorocyclopropyl radical intermediate, which undergoes coupling with a wide range of nucleophiles under copper catalysis.
Article
Chemistry, Organic
Bin Li, Jiang-Ling Shi, Ying Xia
Summary: In this study, a practical method for building all-carbon quaternary centers in gem-difluorinated cyclopropanes was developed using gem-difluorocyclopropyl bromides as a general building block. The reaction involves the participation of a gem-difluorocyclopropyl radical intermediate, which can undergo coupling with a wide range of nucleophiles under copper catalysis.
Article
Chemistry, Multidisciplinary
Taichi Koike, Takeaki Iwamoto
Summary: C4H4 isomers have important implications in understanding the properties of hydrocarbons and their role in combustion and organic reactions in outer space. In this study, a crystalline cyclobutenylidene derivative known as 3-silacyclobut-2-en-4-ylidene (SiCBY) was synthesized via a carbene-to-carbene ring-expansion reaction. SiCBY demonstrated diverse electronic properties, exhibiting strong electron-donating abilities and ambiphilic reactivity towards small gaseous molecules and C-H bonds. This research introduces a novel strategy and molecular motif for accessing low-valent carbon species with unique electronic properties.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Hiroki Tashiro, Masahiro Terada, Itaru Nakamura
Summary: Gold-catalyzed reactions were used to synthesize 2H-azirines with sulfenyl and acyl groups at the 3-position, yielding good to excellent results. These reactions involved internal transfer of sulfinyl oxygen atom and carbene insertion into the N-S bond for ring construction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Yu-Yang Zhang, Han Li, Xiaoding Jiang, Chitreddy V. Subba Reddy, Hao Liang, Yaqi Zhang, Rihui Cao, Raymond Wai-Yin Sun, Man Kin Tse, Liqin Qiu
Summary: A new synthetic method was developed for the synthesis of functional flavones using nickel-catalyzed decarbonylative cycloaddition of benzofuran-2,3-diones with alkynes, with yields ranging from 65% to 99%. Terminal alkynes with substituted phenyl groups and internal alkynes like aryl acyl acetylenes and diphenylacetylenes are suitable substrates for this reaction. The effects of bases on the reactions of different types of alkyne substrates were also investigated and discussed.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Xue Li, Haohua Chen, Qingqing Xuan, Shaoyu Mai, Yu Lan, Qiuling Song
Summary: Inspired by the body circulation of Omeprazole, a novel carbenetriggered cascades for synthesizing 2-aminobenzofuran derivatives from N-sulfonyl-1,2,3-triazoles or benzothioazole-bearing thiocarbamates was disclosed, representing an unprecedented imine derivative migration process. Additionally, desulfurizing reagent-free Barton-Kellogg-type reactions starting from N-sulfonyl-1,2,3-triazoles were achieved for the first time, with elemental sulfur confirmed as a byproduct. Experimental data and DFT calculations further explained the unique reactivity observed in these reactions.
Article
Chemistry, Organic
Tasuku Inami, Takuya Kurahashr, Seijiro Matsubara
Summary: A new nickel-catalyzed insertion reaction has been developed, where an alkyne is inserted into a 2-(trifluoromethyl)-1,3-benzothiazole to yield a novel compound. The structure of the intermediate was confirmed through X-ray single-crystal structure analysis and in situ X-ray absorption fine-structure spectroscopy.
Article
Chemistry, Organic
Bo-Han Zhu, Cang-Hai Shen, Min-Ling Nie, Fumin Zheng, Chengzhe Huang, Fan Chen, Long Li, Chao Deng, Long-Wu Ye, Peng-Cheng Qian
Summary: In this study, a novel non-noble-metal-catalyzed oxidation/cyclization reaction has been developed to synthesize diversely functionalized lactams in moderate to good yields with excellent diastereoselectivities, without the production of typical cyclopropanation products. Furthermore, the combination with another chemical reaction allows for the high diastereo- and enantioselective synthesis of chiral gamma-lactams containing three contiguous stereocenters. Density functional theory calculations suggest that this reaction possibly involves a carbon cation or proton transfer process.
Article
Chemistry, Multidisciplinary
Fei-Hu Cui, Qian Li, Le-Han Gao, Kaidong Ruan, Kexin Ma, Siyuan Chen, Zhengyu Lu, Jiawei Fei, Yu-Mei Lin, Haiping Xia
Summary: The rapid synthesis of tetracyclic metallaaromatics with broad absorption is described in this study. The formation of these unique compounds involves unconventional reactions to broaden the absorption window. These condensed metallaquinolines show high photothermal conversion efficiency, stability, and have numerous potential applications.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Swapnil V. V. Halnor, Pawan S. S. Dhote, Chepuri V. V. Ramana
Summary: A new catalytic method has been developed to construct the quinobenzoxazine core by employing gold-catalyzed cyclization of o-azidoacetylenic ketones in the presence of anthranils. The process involves a 6-endo-dig cyclization of o-azidoacetylenic ketone catalyzed by gold, leading to the formation of an alpha-imino gold carbene, which then transfers to anthranil to form the 3-aryl-imino-quinoline-4-one intermediate. This intermediate undergoes 6 pi-electrocyclization and aromatization to form the central quinobenzoxazine core. This transformation provides a new and scalable approach to diverse quinobenzoxazine structures under mild reaction conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Cong Guan, Jiabin Yin, Jian Ji, Jinhua Liu, Xiang Wu, Tong Zhu, Shunying Liu
Summary: A regioselective electrochemical C-H amination method using easily accessible ethers has been developed to synthesize N (2)-substituted 1,2,3-triazole. Multiple substituents, including heterocycles, were well-tolerated, and 24 examples were obtained in moderate to good yields. Control experiments and DFT calculations revealed that the electrochemical synthesis occurs through a N-tosyl 1,2,3-triazole radical cation process, promoted by single-electron transfer from the lone pair electrons of the aromatic N-heterocycle, and the desulfonation is responsible for the high N (2)-regioselectivity.
Article
Chemistry, Organic
Yujia Gao, Juan Zhang, Wenyu Shan, Weihong Fei, Jinzhong Yao, Weijun Yao
Summary: In this study, a trimerization reaction of gamma-aryl-3-butynoates was achieved through catalysis, leading to the formation of exocyclopentene derivatives with an allcarbon quaternary stereocenter. The reaction exhibited high stereoselectivity and enantioselectivity, delivering optically pure products with high enantiomeric excess values.
Article
Chemistry, Multidisciplinary
Feng-Lin Hong, Chong-Yang Shi, Pan Hong, Tong-Yi Zhai, Xin-Qi Zhu, Xin Lu, Long-Wu Ye
Summary: In this study, a copper-catalyzed asymmetric cascade cyclization/[1,2]-Stevens-type rearrangement was reported to efficiently assemble a variety of valuable chiral chromeno[3,4-c]pyrroles bearing a quaternary carbon stereocenter with generally moderate to good yields and excellent enantioselectivities (up to 99% ee). Notably, this protocol represents the first example of catalytic asymmetric [1,2]-Stevens-type rearrangement based on alkynes and the first asymmetric formal carbene insertion into the Si-O bond.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Yao Zhong, Nathan A. Spahn, Ryan M. Stolley, Minh H. Nguyen, Janis Louie
Article
Chemistry, Inorganic & Nuclear
Ryan M. Stolley, Jonathan M. Darmon, Parthapratim Das, Monte L. Helm
Article
Chemistry, Multidisciplinary
Ryan M. Stolley, Jonathan M. Darmon, Monte L. Helm
CHEMICAL COMMUNICATIONS
(2014)
Article
Chemistry, Multidisciplinary
Ryan M. Stolley, Hung A. Duong, David R. Thomas, Janis Louie
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2012)
Article
Chemistry, Organic
Ryan M. Stolley, Wenxing Guo, Janis Louie
Article
Chemistry, Inorganic & Nuclear
Andrew L. Clevenger, Ryan M. Stolley, Nicholas D. Staudaher, Noman Al, Arnold L. Rheingold, Ryan T. Vanderlinden, Janis Louie
Article
Chemistry, Inorganic & Nuclear
Noman Al, Ryan M. Stolley, Nicholas D. Staudaher, Ryan T. Vanderlinden, Janis Louie
Article
Chemistry, Organic
Jonas Renner, Ashish Thakur, Philipp M. Rutz, Jacob M. Cowley, Judah L. Evangelista, Puneet Kumar, Matthew B. Prater, Ryan M. Stolley, Janis Louie
Review
Chemistry, Multidisciplinary
Andrew L. Clevenger, Ryan M. Stolley, Justis Aderibigbe, Janis Louie
Article
Chemistry, Multidisciplinary
Haoliang Liu, Hans Malissa, Ryan M. Stolley, Jaspal Singh, Matthew Groesbeck, Henna Popli, Marzieh Kavand, Su Kong Chong, Vikram V. Deshpande, Joel S. Miller, Christoph Boehme, Z. Valy Vardeny
ADVANCED MATERIALS
(2020)
