Article
Chemistry, Multidisciplinary
Shuang Qiu, Xin Zhang, Chaopeng Hu, Hongxu Chu, Qianli Li, David A. Ruiz, Liu Leo Liu, Chen-Ho Tung, Lingbing Kong
Summary: In this study, we reveal the reactivity of aryliminoboranes via BNCC π conjugation, enabling the dearomative Diels-Alder-like reactions with aldehydes. This reaction features mild conditions, catalyst-free, and exhibits a broad substrate scope and good functional group tolerance.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Shuheng Xu, Linwei Zeng, Sunliang Cui
Summary: The Diels-Alder (DA) reaction and hetero-Diels-Alder (HDA) reaction are powerful methods for constructing carbocycles and heterocycles. This study presents an integrated building block that combines both DA and HDA reactions, utilizing triazenyl dienes to undergo the DA reaction and the newly released alkene moiety and triazene to engage in the HDA reaction.
Article
Chemistry, Organic
Aurapat Ngamnithiporn, Padon Chuentragool, Poonsakdi Ploypradith, Somsak Ruchirawat
Summary: This article reports the development of a novel three-component aza-Diels-Alder reaction, employing sultines, aldehydes, and amines as substrates. By using Cu(OTf)(2) as a Lewis acid catalyst and the in situ generation of imines, a wide range of polysubstituted tetrahydro-isoquinoline derivatives can be easily prepared from readily available precursors. The synthetic utility of these products is demonstrated through various product transformations, including the synthesis of tricyclic N-heterocycles.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Masao Ohashi, Dan Tan, Jiayan Lu, Cooper S. Jamieson, Daiki Kanayama, Jiahai Zhou, K. N. Houk, Yi Tang
Summary: The synthesis of cis-decalin structures using [4 + 2] cycloaddition with high stereoselectivity is challenging. In this study, we investigated the biosynthetic pathway of the fungal natural product fischerin (1) and identified a novel pericyclase, FinI, which catalyzes this reaction. The cocrystal structure of FinI, a predicted O-methyltransferase, with the product and SAM provides valuable insights into the natural formation of cis-decalin.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Heather O. LeClerc, Rasha Atwi, Sydney F. Niles, Amy M. McKenna, Michael T. Timko, Richard H. West, Andrew R. Teixeira
Summary: Hydrothermal liquefaction (HTL) is a promising strategy for converting organic waste into energy-dense biocrude. This study investigates the distribution and reaction pathways of nitrogen in different hydrothermal products generated from food waste. The results suggest that the Maillard reaction is the dominant pathway for converting reactive nitrogen intermediates into observed products.
Article
Chemistry, Organic
Julia O. Strelnikova, Alexander N. Koronatov, Nikolai Rostovskii, Alexander F. Khlebnikov, Olesya Khoroshilova, Mariya A. Kryukova, Mikhail S. Novikov
Summary: The domino reaction catalyzed by Rh-2(Piv)(4) leads to the formation of N-sulfonylated (Z)-2-(2-aminovinyl)imidazoles, providing a direct and flexible access to the desired compounds.
Article
Chemistry, Multidisciplinary
Jianyang Dong, Andreas Ostertag, Christof Sparr
Summary: In this study, the accessibility of atropisomeric o-quinodimethanes and the enantioselective synthesis of their precursors were described. The catalyst-stereocontrolled [2+2+2] cycloaddition and subsequent stereospecific Diels-Alder reactions enabled the synthesis of enantioselective compounds with high selectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Yan Jiang, Hao-Jie Ma, Xue-Long Wang, Yi Yang
Summary: A Yb(OTf)(3)-catalyzed formal (4 + 3) cycloaddition reaction was successfully achieved using donor-acceptor cyclopropanes and 3-benzylideneindoline-2-thiones as reactants. Functionalized 5,10-dihydro-2H-thiepino[2,3-b]indole derivatives were synthesized with good yields and moderate to good diastereoselectivity. This reaction represents the first (4 + 3) cycloaddition of 3-benzylideneindoline-2-thiones.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Jinbo Zhang, Manli Ma, Rong Zhou, Hongqiang Chu, Xue Wang, Shaojie Wang, Huhu Tian, Zhipeng Yan, Mingtao Li, Zhongyan Wu, Bin Li, Jiafeng Yan, Lan Anh Thi Nguyen, Rongxing Cao, Guoqing Wu, Xianghua Zeng, Hao-Li Zhang, Jaeyong Kim, Lin Wang, Yongjun Tian
Summary: In this study, it is demonstrated using multiple characterization techniques that the bowl-shaped clusters C18Te3Br4(Bu-O)(6) may undergo a Dehydro-Diels-Alder (DDA) reaction at high pressure, resulting in crystalline carbon materials with different transport properties.
Article
Chemistry, Organic
Nan-Fang Mo, Ying Zhang, Zheng-Hui Guan
Summary: An asymmetric organocatalyzed three-component Povarov reaction has been developed to construct azaspirocycles. A chiral phosphoric acid catalyst with a unique structure was highly efficient in the reaction, leading to a wide range of azaspirocycles in high yields and excellent enantioselectivities. This reaction has expanded the scope of the traditional Povarov reaction.
Article
Chemistry, Organic
Gary L. Points, Christopher M. Beaudry
Summary: Substituted carbazoles are efficiently synthesized from 3-triflato-2-pyrones and alkynyl anilines, allowing for multiple substituents with complete control of regiochemistry, resulting in complex substitution patterns. This strategy can also be applied to prepare substituted bicarbazoles and related biaryls, and has been demonstrated in the synthesis of the carbazole natural product clausine C.
Article
Chemistry, Organic
Tao Wang, Wen-Bin Wang, Yan-Ming Fu, Cheng-Feng Zhu, Lan-Jun Cheng, Yang-En You, Xiang Wu, You-Gui Li
Summary: An asymmetric double oxidative [3 + 2] cycloaddition is reported, which generates highly functionalized chiral CF3-containing spiro[pyrrolidin-3,2'-oxindole] with four contiguous stereocenters stereoselectively. This method directly constructs two C-C bonds from four C(sp3)-H bonds, and it features mild conditions, broad substrate scope, and excellent functional group compatibility.
Article
Chemistry, Organic
Yan Jiang, Hao-Jie Ma, Xue-Long Wang, Yi Yang
Summary: A new compound was synthesized successfully in this study by using Yb-(OTf)(3) catalyst to react donor-acceptor cyclopropanes with sulfur-containing 4π components. The reaction showed high yields and moderate to good diastereoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Yongzheng Ding, Min Si, Hanmin Huang
Summary: A palladium-catalyzed tandem carbonylative lactonization and cycloaddition reaction has been developed, allowing efficient conversion of alkenes to various bridged lactones. The strategy can also be used for intramolecular tandem hydrocarbonylative lactonization and cycloaddition reactions to access more complex bridged lactones.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Shaolei Ding, Yingbo Shi, Baochao Yang, Min Hou, Haibing He, Shuanhu Gao
Summary: We describe the asymmetric total synthesis of periglaucines A-C, N,O-dimethyloxostephine and oxostephabenine. Key strategies include a regio- and diastereoselective Hayashi-Miyaura reaction, an intramolecular photoenolization/Diels-Alder reaction, and a bio-inspired intramolecular Michael addition and transannular acetalization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Multidisciplinary
Rong Fan, Chen Tan, Yongguo Liu, Yun Wei, Xiaowen Zhao, Xinyuan Liu, Jiajing Tan, Hiroto Yoshida
Summary: Sulfonium salts and sulfur ylides are important S(IV) motifs with unique reactivities for synthesizing sulfur containing compounds. Significant developments have been observed in this field in recent years. This review aims to provide a concise overview of the recent advances in sulfonium salt and sulfur ylide chemistry.
CHINESE CHEMICAL LETTERS
(2021)
Review
Chemistry, Applied
Shintaro Kamio, Hiroto Yoshida
Summary: Recent advances in the synthesis of organoboron compounds with diminished boron Lewis acidity via B(aam)- and B(dan)-installing borylation reactions have attracted growing attention due to their unique reactivity and outstanding stability toward air and moisture. Direct Suzuki-Miyaura cross-couplings with previously believed unreactive R-B(aam)/B(dan) compounds have also been discussed.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Polymer Science
Yoshikazu Teshima, Masahiko Saito, Tsubasa Mikie, Kimihiro Komeyama, Itaru Osaka
Summary: Studies have shown that bithiazole dicarboxylate ester (BETz) is a promising building unit for pi-conjugated polymers, with copolymers forming highly crystalline structures in thin films, which is beneficial for semiconducting properties.
Article
Chemistry, Multidisciplinary
Hiroto Yoshida
Summary: In this study, a B(dan) moiety of diminished boron-Lewis acidity was efficiently installed into organic frameworks through copper catalyzed three-component carboboration of alkenes. The resulting dan-substituted organoboranes were obtained via borylative substitution of carbon electrophiles. Additionally, synthesis of diverse organostannanes based upon copper-catalyzed carbostannylation and borylstannylation have been described, where the Lewis acidity increment of a tin center facilitated the progress in some cases.
Article
Chemistry, Organic
Shintaro Kamio, Taiki Imagawa, Masaaki Nakamoto, Martin Oestreich, Hiroto Yoshida
Summary: Trialkylsilyllithium species can be easily generated under specific conditions and trapped by boron electrophiles. This method allows for the preparation of silylboronic esters.
SYNTHESIS-STUTTGART
(2021)
Correction
Chemistry, Organic
Shintaro Kamio, Taiki Imagawa, Masaaki Nakamoto, Martin Oestreich, Hiroto Yoshida
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Physical
Takumi Tsushima, Hideya Tanaka, Kazuki Nakanishi, Masaaki Nakamoto, Hiroto Yoshida
Summary: The highly internal-selective borylation of terminal alkynes under copper catalysis was achieved by diminishing boron-Lewis acidity and introducing ligand-derived steric bulk around a copper center. The use of an anthranilamide-substituted boron moiety enabled internal regioselectivity and Suzuki-Miyaura cross-coupling activity to be compatibly achieved, providing a direct and universal approach to variously substituted branched alkenylboron compounds.
Article
Chemistry, Organic
Ikuo Kageyuki, Jialun Li, Hiroto Yoshida
Summary: In this study, an unsymmetrical diboron was smoothly added across various terminal alkynes under platinum catalysis, resulting in the regio- and stereoselective formation of cis-vic-diborylalkenes. The use of a highly electron-deficient triarylphosphine ligand, P(BFPy)(3), is crucial for the regiocontrol, and electron deficiency in ligands has been proven to be closely correlated with the regioselectivity.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Hiroto Yoshida
Summary: Lewis acidity-diminished boron functionalities can be efficiently incorporated into organic frameworks through various catalytic borylation reactions, and can be utilized for direct cross-coupling. We have also developed copper-catalyzed arylation and cyanostannylation reactions, in which the Lewis acidity increment of a tin center facilitates their progress.
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
(2022)
Article
Chemistry, Applied
Mikinao Koishi, Kazuki Tomota, Masaaki Nakamoto, Hiroto Yoshida
Summary: We report the direct Suzuki-Miyaura coupling of saturated organoboron compounds with dan substituents. Despite the reduced Lewis acidity of the boron center, cyclopropyl-B(dan) can be activated by t-BuOK to undergo transmetalation with a palladium complex. The increased s-character of the C-B(dan) bond is likely crucial for this reaction.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Hideya Tanaka, Masaaki Nakamoto, Hiroto Yoshida
Summary: The Lewis acidity of organoboronates [B(pin), B(neop), B(cat), B(eg), B(nad)] and organoboronamides [B(dan), B(aam), B(mdan)] can be uniformly evaluated by computed ammonia affinity (AA), but other methods (LUMO energies, global electrophilicity index (GEI), fluoride ion affinity (FIA)) are only partially applicable. The relationships between the AA values and structural characters including the B-X bond lengths, the X-B-X angles, and the changes in the B-X bond lengths in the formation of the ammonia adducts were also described.
Article
Chemistry, Multidisciplinary
Taiki Imagawa, Kazuki Okazawa, Kazunari Yoshizawa, Hiroto Yoshida, Rong Shang, Yohsuke Yamamoto, Masaaki Nakamoto
Summary: The formation of Lewis pairs is an important concept in chemistry. Recently, the complexation of Lewis acid tris(pentafluorophenyl)borane with Lewis base moieties and subsequent reduction has been explored as a strategy for designing new reactions and structures. Through synthesis, X-ray crystallography, spectroscopic analysis, and quantum chemical calculations, it was found that Lewis adduct formation stabilizes an antiaromatic system consisting of 9,10-dicyanoanthracene and tris(pentafluorophenyl)borane. The reduction of a bisboron complex also resulted in a decrease in antiaromaticity.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Kazuki Tomota, Yuki Izumi, Kazuki Nakanishi, Masaaki Nakamoto, Hiroto Yoshida
Summary: A direct and transition metal-free method for the installation of B(dan) into organic frameworks has been developed. Heteroaryl-H bonds can be transformed into heteroaryl-B(dan) bonds through deprotonation. The resulting heteroaryl-B(dan) compounds, which are typically difficult to access, can undergo direct Suzuki-Miyaura coupling. The method has also been demonstrated to be applicable to silicon nucleophiles, leading to the formation of Lewis acidity-diminished stable silyl-B(dan) and -B(aam) in one pot.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Hiroto Yoshida, Yuki Izumi, Yuta Hiraoka, Kazuki Nakanishi, Masaaki Nakamoto, Sayaka Hatano, Manabu Abe
Summary: This article describes the synthesis of a new stable compound PhMe2Si-B(dan) and its application in catalytic silylboration and silylation reactions of alkynes.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Multidisciplinary
Kimihiro Komeyama, Takuya Michiyuki, Yoshikazu Teshima, Itaru Osaka
Summary: The scope of the Giese reaction is expanded using readily available alkyl tosylates as substrates and nucleophilic cobalt(i) catalysts under visible-light irradiation, preferentially with less bulky primary alkyl tosylates. This unique reactivity enables the regio-selective Giese reaction of polyol derivatives.
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
