Article
Chemistry, Organic
Xin Geng, Heng He, Andrey Shatskiy, Elena V. Stepanova, Gregory R. Alvey, Jian-Quan Liu, Markus D. Karkas, Xiang-Shan Wang
Summary: This study presents a straightforward synthetic approach for constructing phenanthridin-6(5H)-one skeletons. The method utilizes palladium catalysis and provides controlled access to various functionalized phenanthridin-6(5H)-ones in yields ranging from 59% to 88%. Plausible reaction pathways are proposed based on mechanistic experiments.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Xin Geng, Heng He, Andrey Shatskiy, Elena V. Stepanova, Gregory R. Alvey, Jian-Quan Liu, Markus D. Karkas, Xiang-Shan Wang
Summary: A straightforward synthetic approach for the construction of phenanthridin-6-(5H)-one skeletons is reported. Palladium catalysis is used to provide controlled access to a range of functionalized phenanthridin-6-(5H)-ones in yields of 59-88%. Plausible reaction pathways are proposed based on mechanistic experiments.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Hao Wu, Shi-Hui He, Hai-Tao Qin, Feng Liu
Summary: This study reports a photoredox-catalyzed formal [5 + 2] annulation reaction that rapidly synthesizes structurally diverse alkene/alkyne-containing oxepanes by reacting N-alkoxypyridiniums with 1,3-dienes/1,3-enynes. The reaction selectively functionalizes distal unactivated C(sp(3))-H bonds and has a broad substrate scope, allowing for the transformation of complex natural products. A radical mechanism involving oxygen-directed 1,5-hydrogen atom transfer, facile coupling of alkyl radicals with 1,3-dienes/1,3-enynes, and the construction of oxepane motifs via C-O bond formation is proposed.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Zhizhou Chen, Xiangwen Kong, Shengtong Niu, Shuang Yang, Jinggong Liu, Bolai Chen, Benlong Luo, Changyu Zhou, Chenglin Ding, Xinqiang Fang
Summary: Asymmetric construction of cyclopentenones using N-Heterocyclic carbene catalysis with enals and alpha-diketones has been achieved, yielding a series of highly functionalized cyclopentenones in a highly diastereo- and enantioselective manner. The protocol is tolerant of substrates with both aromatic and aliphatic groups, and further transformations of the products have led to a range of value-added molecules.
Article
Chemistry, Organic
Siyang Xing, Yuhan Wang, Changkun Jin, Shaochen Shi, Yihui Zhang, Ziya Liao, Kui Wang, Bolin Zhu
Summary: In this study, a method for intramolecular formal [3+2] cycloaddition of activated aziridines and epoxides with electron-deficient alkene was developed, enabling efficient construction of bridged aza- and oxa-[n.2.1] skeletons. This strategy proved to be highly efficient with the assistance of lithium iodide.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Hongbo Qi, Kaiming Han, Shufeng Chen
Summary: This study presents a convenient palladium-catalyzed domino cyclization reaction for the synthesis of bis(benzofuranyl)methane scaffolds bearing all-carbon quaternary center, in which multiple bonds and rings are formed in a single synthetic sequence through a cascade reaction. The approach demonstrates broad substrate scope and good functional-group tolerance, and has been successfully applied to the synthesis of benzofuranyl methyl chromane derivatives.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Siyang Xing, Chenyu Wang, Tingxuan Gao, Yuhan Wang, Hongzheng Wang, Hanfei Wang, Kui Wang, Bolin Zhu
Summary: A stepwise cyclization method has been developed for the synthesis of 4-spiroannulated tetrahydroisoquinoline compounds, which involves sequential ring opening of aziridines and Pictet-Spengler reaction. This strategy exhibits high bonding and cyclization efficiency, broad substrate scope, mild reaction conditions, and good generality of the ring size in the product.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Applied
Jun-Sheng Wei, Zi-Yu Xu, Yin Wei, Min Shi
Summary: In this paper, a gold(I)-catalyzed cascade cyclization of N- or O-nucleophile tethered-vinylidenecyclopropanes (VDCPs) is reported, leading to the synthesis of pyrrole, furan, pyrrolidine, and piperidine skeletons in 30%-98% yields. The reaction pathways depend on the carbon chain length connecting the nucleophile and VDCPs, resulting in different products. By using α-amino VDCPs and α-hydroxyl VDCPs with a methylene group as the connection, intramolecular nucleophilic addition and aromatization occur, followed by ring-opening of the cyclopropane unit to produce substituted pyrroles and furans. Extending the chain length to three or four carbons enables the formation of pyrrolidines and piperidines with a cyclobutene moiety through ring expansion of the cyclopropane unit and gold carbene induced vinylogous nucleophilic addition.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Applied
Juan C. Nieto-Carmona, Ines Manjon-Mata, M. Teresa Quiros, Gema Caballero-Santiago, Fernando Perez-Maseda, Diego J. Cardenas
Summary: In this study, we report the Ni-catalyzed cycloisomerization of 1,5-allenynes, which can yield different products depending on the substrates used. Internal alkynes can form fused bicyclic compounds, while those with terminal alkynes can generate cyclopentene derivatives. The mechanism of the reaction was also investigated and a catalytic cycle involving Ni(0)-Ni(II) species was proposed.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Meng-Lian Yao, Xiao-Yuan Wang, Guang-Chao Feng, Ji-Kai Liu, Bin Wu, Jin-Ming Yang
Summary: A novel palladium(II)-catalyzed intramolecular [2 + 2 + 2] annulation of indolyl 1,3-diynes is described, resulting in the synthesis of various azepino-fused carbazoles in moderate to excellent yields. The success of this transformation is attributed to the use of a carboxylic acid additive. This method exhibits broad functional group tolerance, easy handling in air, and 100% atom economy. Additionally, the scalability, late-stage derivatization, and photophysical property investigations demonstrate the potential synthetic utility of this methodology.
Article
Chemistry, Applied
Wei-Min Feng, Xian-Ming Liu, Li-Jun Xiao, Qi-Lin Zhou
Summary: We have developed a new method for synthesizing tricyclic [1,2-a]indoles using nickel-catalyzed reactions. This method shows high synthetic utility and can be used to obtain useful indole amine compounds through conversion.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Yunlong Zhao, Chen-Fei Liu, Leroy Qi Hao Lin, Albert S. C. Chan, Ming Joo Koh
Summary: In this study, a N-heterocyclic carbene-Ni-I catalytic species was used to achieve highly substituted alkenes from abundant monosubstituted substrates with excellent regio- and stereoselectivities. Trimethylsilyl triflate and trimethylamine additives were added to mediate the reaction, resulting in the generation of trisubstituted boron- and arene-containing trans alkenes. This method represents a significant addition to the toolbox of reactions for the concise synthesis of unsaturated biologically active compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Jian Xiao, Ya-Wen Wang, Zhong-Ping Qiu, Yu Peng
Summary: The facile access to the tetracyclic skeleton of podophyllotoxin, a medicinally important lignan natural product, was efficiently achieved via a unique intramolecular alkylarylation of the tethered alkene in a dihalide under mild conditions using reductive nickel catalysis.
Article
Chemistry, Organic
Shengnan Lin, Jianchao Cui, Yu Chen, Yi Li
Summary: A copper-catalyzed trifluoromethylarylated cycloaddition of imidazoles and olefins using CF3SO2Cl as the radical source was reported, leading to the synthesis of highly functionalized tricyclic imidazoles. The procedure showed a wide substrate scope with isolated yields ranging from 25% to 93% (36 examples). Mechanistic studies supported a free trifluoromethyl radical pathway.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Talia J. Steiman, Annah E. Kalb, James C. Coombs, Justin K. Kirkland, Hector Torres, Daniel H. Ess, Christopher Uyeda
Summary: The study investigates the reductive cyclization of 1,1-dichloroalkenes using a dinickel catalyst, with mechanistic studies supporting the intermediacy of a Ni-2(vinylidene) species. The results suggest that both nickel centers cooperate in mediating key steps in the cyclization mechanism.
Article
Chemistry, Organic
Tsuyoshi Mita, Hiroki Masutani, Sho Ishii, Yoshihiro Sato
Article
Chemistry, Multidisciplinary
Yoshihiro Oonishi, Shuichi Masusaki, Shunki Sakamoto, Yoshihiro Sato
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Multidisciplinary
Koichi Katagiri, Haruka Kodera, Masanori Tayu, Nozomi Saito
Article
Chemistry, Applied
Tsuyoshi Mita, Masashi Uchiyama, Yoshihiro Sato
ADVANCED SYNTHESIS & CATALYSIS
(2020)
Article
Chemistry, Organic
Toshiki Akiyama, Yuki Wada, Makito Yamada, Yasunori Shio, Tetsuo Honma, Shuhei Shimoda, Kazuki Tsuruta, Yusuke Tamenori, Hitoshi Haneoka, Takeyuki Suzuki, Kazuo Harada, Hayato Tsurugi, Kazushi Mashima, Jun-ya Hasegawa, Yoshihiro Sato, Mitsuhiro Arisawa
Article
Chemistry, Physical
Ryohei Doi, Koji Shimizu, Yuma Ikemoto, Masashi Uchiyama, Mikiko Koshiba, Atsushi Furukawa, Katsumi Maenaka, Satoshi Watanabe, Yoshihiro Sato
Summary: This study reports a nickel-catalyzed cascade reaction to construct a 3-acylbenzo[b]furan skeleton. Through reaction condition optimization, the catalyst loading could be reduced to 5-10 mol %, leading to the synthesis of various functionalized compounds. Stoichiometric study of nickel complexes and DFT calculations were conducted to support a possible reaction mechanism.
Article
Chemistry, Multidisciplinary
Ryohei Doi, Kanako Hayashi, Yoshihiro Sato
Summary: In this study, palladium-catalyzed decarboxylative alpha-polyfluoroarylation of ketones was reported. By screening reaction conditions, XPhos and Ruphos were selected as ancillary ligands for Pd(0) catalysts, enabling the reaction to be applied to various substrates. A cross-over experiment was conducted to gain insight into the reaction mechanism.
Article
Chemistry, Organic
Yoshihiro Oonishi, Shunki Sakamoto, Shuya Agata, Yoshihiro Sato
Summary: In the Rhodium(I)-catalyzed enantioselective cyclization of enynes, the presence of different functional groups on the substrate molecules affects the structure and yield of the products, with C(sp(3))-H bond activation being an important high energy barrier step in the cyclization reaction.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Souta Misawa, Asaki Miyairi, Yoshihiro Oonishi, Steven P. Nolan, Yoshihiro Sato
Summary: Polarized alkynes such as ynol ethers and ynamides undergo Au(I)-catalyzed hydroalkoxylation/Claisen rearrangement cascade reactions with allylic alcohols, proceeding under mild conditions with high regioselectivity. The resulting gamma,delta-unsaturated esters or amides are formed in an atom-economical manner using the [Au(IPr)NTf(2)] catalyst.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Applied
Yoshihiro Oonishi, Kazuki Takagishi, Yi-Min Liu, Yoshihiro Sato
Summary: This article describes the rhodium-catalyzed enantioselective hydroacylation of racemic alkynals with a substituent at the alpha-position of the carbonyl group. The reaction can be applied to a wide range of substrates (22 examples), and mechanistic studies reveal a dynamic kinetic resolution (DKR) process during the hydroacylation, leading to various cyclic ketones with yields of 47-93% and enantiomeric ratios (er) of 59:41 to 97:3 from racemic starting materials.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Koji Yamada, Kaho Ishizawa, Yoshihiro Oonishi, Yoshihiro Sato, Takahide Nishi
Summary: This study presents a practical synthetic method for accessing oxazolidinone-2,3-fused indoline and azaindoline derivatives through one-pot cyclization. These derivatives, which contain sp3-hybridized carbons, could serve as novel scaffolds in medicinal chemistry.
Article
Chemistry, Organic
Mikiko Koshiba, Yuto Furuki, Kazuhiro Morisaki, Ryohei Doi, Yoshihiro Sato
Summary: We report a nickel-catalyzed migratory cycloisomerization reaction for the synthesis of 2,3-disubstituted indoles. The reaction proceeds via acyl transfer on the nitrogen atom of the substrate to the C3 position in the product, and a suitable N-heterocyclic carbene ligand is used in the reaction.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Asaki Miyairi, Yoshihiro Oonishi, Yoshihiro Sato
Summary: This study successfully demonstrated the one-pot synthesis of fully substituted 2-aminofurans via a gold-catalyzed cascade reaction, under highly mild conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Inorganic & Nuclear
Ryohei Doi, Yoshihiro Sato
NICKEL CATALYSIS IN ORGANIC SYNTHESIS: METHODS AND REACTIONS
(2020)
Meeting Abstract
Chemistry, Multidisciplinary
Toshiki Akiyama, Tetsuo Honma, Kazuki Tsuruta, Yusuke Tamenori, Yohei Ueda, Hayato Tsurugi, Kenichi Murai, Ohno Shohei, Kazushi Mashima, Hiromichi Fujioka, Yoshihiro Sato, Mitsuhiro Arisawa
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2019)