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
Yinchao Zhang, Wenxiu Xu, Tongtong Gao, Mengjuan Guo, Chun-Hua Yang, Hua Xie, Xiangtao Kong, Zhantao Yang, Junbiao Chang
Summary: A Pd-catalyzed borylsilylative cyclization of 1,6-allenynes with PhMe2SiBpin was developed, providing a practical and general method to synthesize carbocycles and heterocycles bearing silyl and boryl groups with high regioselectivities and stereoselectivities.
Article
Chemistry, Organic
Tao Wang, Ji-Xun Guan, Yun-Xuan Tan, Ping Tian
Summary: This paper reports the first cobalt-catalyzed highly selective arylation carbocyclization reaction of 1,6-allenynes with arylboronic acids. The reaction demonstrates moderate to high yields, broad substrate scope, and good compatibility with functional groups.
Article
Chemistry, Multidisciplinary
Debayan Roy, Beeraiah Baire
Summary: A new Cu-II-catalyzed tandem cycloisomerization-[3+2] cyclodimerization reaction of 1-(indol-2-yl)pent-4-yn-3-ol has been developed, providing access to structurally unprecedented dimeric tetrahydrocarbazoles fused to a tetrahydrofuran unit. This strategy allows for the construction of multiple C-C and C-O bonds, creation of stereocenters, and formation of multiple rings in a single operation. A chiral pool version using enantio- and diastereopure substrate was also demonstrated.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Hitomi Tsuno, Jingfeng Shen, Hiroki Komatsu, Norihito Arichi, Shinsuke Inuki, Hiroaki Ohno
Summary: A gold-catalyzed cascade cyclization of naphthalene-tethered allenynes leads to strained fused phenanthrene derivatives. The reaction involves the nucleophilic reaction of an alkyne with an activated allene to generate a vinyl cation intermediate, followed by arylation with a tethered naphthalene ring to form the 4H-cyclopenta[def]phenanthrene (CPP) scaffold. The gold-catalyzed reaction of aryl-substituted substrates on the alkyne terminus also produces dibenzofluorene derivatives alongside the CPP derivatives, depending on the reaction conditions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Jie Wang, Hui Qian, Shengming Ma
Summary: In this contribution, a palladium-catalyzed cross-coupling reaction was developed for the synthesis of conjugated allenynes. The reaction showed excellent efficiency and selectivity, resulting in high yields of diversely substituted allenynes. The synthetic method demonstrated potential utility in gram-scale reactions and synthetic transformations.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Velautham Saravanan, Masilamani Jeganmohan
Summary: This study describes a palladium-catalyzed tandem reaction of 7-oxabenzonorbornadienes with organic carboxylic acids, which produces cis-1,2-dihydro-l-naphthyl derivatives with moderate to good yields and high diastereoselectivity. A proposed reaction mechanism involving syn acylation, insertion, and diastereoselective ring-opening with 7-oxabenzonorbornadienes explains the reaction.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Kua-Fei Wei, Qing Liu, Guang Ma, Xiao-Lei Jiang, Xiu-Hong Zhu, Guang-Xin Ru, Wen-Bo Shen
Summary: A copper-catalyzed hetero Diels-Alder reaction of allenynes with cis diazenes has been developed to efficiently synthesize a diverse array of valuable polycyclic N-heterocycles. The reaction exhibits temperature control and stereocontrol, leading to the synthesis of tetracyclic pyrrolidines, pentacyclic triazepanes, and tricyclic pyrrolidines.
COMMUNICATIONS CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Liye Chen, Katerina G. Malollari, Adam Uliana, John F. Hartwig
Summary: The lack of functional groups in polyolefins limits their applications, but the functionalization of C-H bonds holds promise for incorporating functionalities into ethylene and linear alpha-olefins polymers. The selective functionalization of polyolefins derived from branched alkenes has not been achieved due to steric effects, but a polyfluorinated ruthenium-porphyrin catalyst successfully incorporates ketone units into polyisobutene without chain cleavage, resulting in a thermally stable polymer with enhanced wetting properties.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Giacomo Mari, Matteo Corrieri, Lucia De Crescentini, Gianfranco Favi, Stefania Santeusanio, Fabio Mantellini
Summary: Substituted 1-aminopyrroles can be easily accessed through an iron-catalyzed cascade reaction of 1,2-diaza-1,3-dienes, which involves a [4+2] cyclodimerization and ring contraction process. The presence of activated hydrogen in the terminal position of the azo-enic moiety is crucial for the synthesis of pyrroles.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Anna N. Philippova, Daria V. Vorobyeva, Pavel S. Gribanov, Ivan A. Godovikov, Sergey N. Osipov
Summary: An efficient method for the selective preparation of trifluoromethyl-substituted azepin-2-carboxylates and their phosphorous analogues has been developed via Cu(I)-catalyzed tandem amination/cyclization reaction of functionalized allenynes with primary and secondary amines.
Article
Chemistry, Applied
Ines Manjon-Mata, M. Teresa Quiros, Elena Velasco-Juarez, Elena Bunuel, Diego J. Cardenas
Summary: A diastereoselective synthesis of borylated bicyclic 5-5 fused ring systems has been achieved through a domino Ni-catalyzed hydroborylative polycyclization of allenynes, providing two new C-C bonds and one C-B bond. The reaction is atom-economical, rapid, and tolerant to functional groups. The process involves oxidative cyclometallation, sigma-metathesis, and 1,2-insertion into the Ni-H bond, followed by reductive elimination.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Yun-Xuan Tan, Shijia Li, Lijuan Song, Xinhao Zhang, Yun-Dong Wu, Jianwei Sun
Summary: The first geminal hydroborative cyclization of enynes is disclosed in this study. Unlike known hydroborative cyclizations, this reaction adds hydrogen and boron to the same position, leading to a new reaction mode. By using a specific catalyst, a variety of gem-hydroborated bicyclic products with a cyclopropane unit can be rapidly formed from simple enyne substrates. Control experiments and calculations provide important insights into the reaction mechanism. Notably, two competing pathways may operate, depending on the substrate.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Hiroki Komatsu, Takaya Ikeuchi, Hitomi Tsuno, Norihito Arichi, Kosuke Yasui, Shinya Oishi, Shinsuke Inuki, Aiko Fukazawa, Hiroaki Ohno
Summary: A novel method based on gold-catalyzed cascade cyclization of aminoallenynes for the direct construction of tricyclic nitrogen heterocycles is described. Efficient synthesis of 1,2-dihydrobenzo[cd]indole derivatives was achieved by promoting the expected biscyclization reaction of hydroxyisobutyryl-protected aminoallenynes with a catalytic amount of BrettPhosAuNTf(2) in the presence of iPrOH. The resulting tricyclic products were further converted into nitrogen-containing polycyclic aromatic compounds (N-PACs) with highly conjugated pi-electron systems.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Chun-Hua Yang, Xiangkun Sun, Congcong Niu, Zhiwei Zhang, Mingzhu Liu, Fangjie Zheng, Ling Jiang, Xiangtao Kong, Zhantao Yang
Summary: This metal-free reaction method allows the construction of different valuable compounds based on the substituents of the allene, with conjugative and sterically hindered phenyl groups favoring the formation of 3,5-dihydroazepine derivatives.
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)
