Article
Chemistry, Multidisciplinary
Che-Sheng Hsu, Carlos R. Goncalves, Veronica Tona, Amandine Pons, Marcel Kaiser, Nuno Maulide
Summary: The article presents a method of synthesizing amine compounds using highly electron-deficient iminium ions and highlights its broad applicability through a specific case study.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Organic
Hai-Bin Yang
Summary: The field of nucleophilic organocatalysis has gained significant interest and utility in the past two decades. This review highlights the recent advancements in single-electron nucleophilic organocatalysis, categorizing them based on the type of catalyst and emphasizing strategies for radical generation and new bond formation. It also provides an overview of the relationships among different nucleophilic organocatalysis and prospects for future development.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Oriol Galeote, Stuart C. D. Kennington, Miguel Mellado-Hidalgo, Anna M. Costa, Pedro Romea, Felix Urpi
Summary: This article describes the development and optimization of oxocarbenium cations and their applications in the synthesis of natural products. By utilizing the high reactivity of oxocarbenium species derived from acetals, glycals, and orthoesters with metal enolates, a series of stereoselective aldol-like processes have been developed.
Article
Chemistry, Organic
Erika Mezo, Mihaly Herczeg, Fruzsina Demeter, Ilona Bereczki, Magdolna Csavas, Aniko Borbas
Summary: The reductive opening of cyclic acetals has been widely used in the introduction of protecting groups in synthetic organic chemistry. This study systematically investigated the efficacy of various reagent combinations in the regioselective cleavage of glucosidic 4,6-halobenzylidene acetals, leading to the successful introduction of versatile halobenzyl protecting groups. The study identified several reagent combinations that efficiently cleaved the acetal rings with high regioselectivity, demonstrating the potential for practical applications in organic synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Xian Xu, Qianlin Sun, Xin Xu
Summary: This work presents a chemo- and stereoselective benzylic C(sp(3))-H alkenylation of tertiary ortho-methyl anilines with internal alkynes using a beta-diketiminato scandium catalyst. The protocol offers an efficient method for synthesizing a new family of tertiary ortho-allylanilines in high yields, which can be further transformed into other valuable anilines. A cationic scandium benzyl species was identified as the catalytic intermediate.
Article
Chemistry, Organic
Hongjun Jeon, Sang Won Choi, Soojun Park, Seokwoo Lee, Sanghee Kim
Summary: In this study, a facile method for generating O-acyloxocarbenium ions (AOIs) from ester and acetal groups was presented, resulting in a unique bridged bicyclic system. The proposed mechanism for the reaction was based on experimental and computational studies, revealing the formation pathway through an epoxonium-like transition state.
Review
Biotechnology & Applied Microbiology
Sang-Woo Han, Jong-Shik Shin
Summary: Aromatic L-amino acid decarboxylases (AADCs) catalyze the conversion of aromatic L-amino acids into aromatic monoamines. Microbial AADCs have limited distribution but hold significant potential for biomedical applications.
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY
(2022)
Article
Biochemistry & Molecular Biology
Dmitry L. Lipilin, Alexander E. Frumkin, Alexey Y. Tyurin, Vitalij V. Levin, Alexander D. Dilman
Summary: This study describes a reaction involving aromatic halides with electron-withdrawing groups and tertiary amines in the presence of an iridium catalyst under blue light irradiation. The products obtained are the result of aromatic substitution of the halide by the dialkylamino fragment. The interaction between aryl radicals and tertiary amines to form zwitterionic radical species is believed to be the main factor contributing to the reaction efficiency.
Review
Chemistry, Multidisciplinary
Maria Tereza M. Martins, Flaviana Rodrigues F. Dias, Raphael Silva M. de Moraes, Marcos Felipe da Silva, Kaio R. Lucio, Karin D'Oliveira Goes, Patrick A. do Nascimento, Andre S. S. da Silva, Vitor F. Ferreira, Anna C. Cunha
Summary: This article provides an overview of multicomponent reactions (MCRs) that involve ortho-quinone methide intermediates (o-QM) and discusses their applications in organic synthesis and biological processes. QMs are generated through eliminative processes or photochemical reactions and can undergo various types of reactions.
Review
Chemistry, Multidisciplinary
Ken Kamikawa
Summary: Although arynes are usually fleeting intermediates, they are highly useful in synthetic applications due to their ability to introduce aromatic rings and form new bonds at multiple sites. Asymmetric catalysis for capturing arynes has been a challenging goal in aryne chemistry, as it requires sufficient interactions between the short-lived arynes and reactive intermediates in a stereo-controlled manner. This review highlights recent advances in asymmetric reactions using arynes, including diastereoselective, enantioselective, and catalytic enantioselective reactions.
NATURE REVIEWS CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Chaorong Wang, Zhencheng Lai, Hujun Xie, Sunliang Cui
Summary: This study demonstrated the use of triazenyl alkynes as versatile building blocks in multicomponent reactions, leading to the synthesis of beta-amino amides with high diastereoselectivity and structural diversity. The bifunctionality of triazenyl alkynes, acting as both C2 fragment and directing group, played a crucial role in achieving the desired outcomes. Furthermore, the triazenyl group allowed for diverse late-stage transformations, opening up new possibilities for building block discovery and rational design of MCRs.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Biochemistry & Molecular Biology
Brenno A. D. Neto, Pedro S. Beck, Jenny E. P. Sorto, Marcos N. Eberlin
Summary: This article discusses the problems associated with using melting points to characterize the products and intermediates of multicomponent reactions (MCRs), highlighting the serious potential for misinterpretation and misleading conclusions. Despite the inherent non-confirmatory nature of melting points, many publications continue to rely on this method for structural confirmation, contradicting best practices in organic synthesis. Precautions are recommended to avoid future confusion in the MCRs field.
Article
Chemistry, Organic
Tania Xavier, Sylvie Condon, Christophe Pichon, Erwan Le Gall, Marc Presset
Summary: The decarboxylative Mannich reaction using DABCO as an organocatalyst allows for the synthesis of beta(2,3)-aminoesters with the syn diastereomer as the major product. An alternative multicomponent protocol has also been developed to enhance the overall eco-compatibility of the process.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Inorganic & Nuclear
Dmitry Moiseev, Brian R. James
Summary: Phosphorus-based Mannich reactions involving primary or secondary phosphines with carbonyl compounds and amines provide a powerful synthetic tool for the design and development of future ligands.
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
(2022)
Article
Chemistry, Multidisciplinary
Hua-Wei Liu, Dian-Liang Wang, Nan-Quan Jiang, Hai-Yan Li, Zhong-Jian Cai, Shun-Jun Ji
Summary: This study presents a novel sequential ring opening reaction of aza-cyclobutanone oxime esters with isocyanides, leading to the synthesis of various compounds under mild conditions. Selective cleavage reactions can be achieved by changing the iron-catalyst system, providing new opportunities for reaction design.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Yuka Sakurai, Yohei Ogiwara, Norio Sakai
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Organic
Norio Sakai, Retsu Shimada, Yohei Ogiwara
Summary: A novel InBr3/PhSiH3 reducing system in a 1,4-dioxane solution efficiently deoxygenated a variety of sulfoxides, leading to the easy preparation of sulfide derivatives. It also exhibited higher reactivity towards sulfoxides compared to commonly reducible functional groups.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yuka Sakurai, Kana Ikai, Kazuki Hayakawa, Yohei Ogiwara, Norio Sakai
Summary: The catalytic intramolecular cyclization of acyl fluorides using a Pd(OAc)(2)/PCy3 system is described, which can be applied to the synthesis of indenofluorenedione derivatives and the construction of other molecules with fivemembered rings. The reaction proceeds via an intramolecular coupling between aromatic C-H bonds with acyl C-F bonds, using a wide range of 2-arylbenzoyl fluoride derivatives as fluorenone precursors.
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2021)
Article
Chemistry, Multidisciplinary
Takumi Nakajima, Ken Takano, Hiromu Maeda, Yohei Ogiwara, Norio Sakai
Summary: The study shows that disilathiane is effective in mediating the synthesis of alkyl aryl sulfides, promoting cleavage of disulfides to generate thiosilane. Diselenides can also be used in this transformation to produce corresponding selenides.
CHEMISTRY-AN ASIAN JOURNAL
(2021)
Article
Chemistry, Organic
Norio Sakai, Kohei Minato, Shota Nakata, Yohei Ogiwara
Summary: We have developed a two-step synthesis for dibenzotetra-thiafulvalene (DBTTF) derivatives by combining the indium-catalyzed reductive dithioacetalization of oxalic acid and electron-rich aromatic dithiols with a subsequent oxidation of the resulting dithioacetals.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Inorganic & Nuclear
Norio Sakai, Mio Ishii, Shouya Tsukahara, Yohei Ogiwara
Summary: This research presents a novel method for the iodine-promoted C-H sulfidation of electron-deficient fluorine-containing aromatic compounds with benzenethiols, enabling the unsymmetrical bis-sulfidation of pentafluorobenzene. Additionally, this oxidizing system could be used for the C-H selenation of fluorine-containing aromatic compounds, leading to the introduction of two different chalcogen atoms on tetrafluorobenzene derivatives.
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
(2022)
Correction
Chemistry, Organic
Norio Sakai, Kohei Minato, Shota Nakata, Yohei Ogiwara
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Inorganic & Nuclear
Hiroyuki Hattori, Yohei Ogiwara, Norio Sakai
Summary: This article reports the formation of benzoyl(benzoato)palladium complexes through a stoichiometric reaction, and elucidates the generation mechanism and applications of the complex.
Article
Chemistry, Organic
Hiroyuki Hattori, Kento Ishida, Yohei Ogiwara, Norio Sakai
Summary: In this study, a new synthetic method for acyl fluorides was developed through a phosphine-catalyzed acyl-group exchange reaction. This is the first example of utilizing an acyl fluoride as a deoxyfluorination reagent.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Takumi Nakajima, Ryuki Takeuchi, Keita Oomori, Kento Ishida, Yohei Ogiwara, Norio Sakai
Summary: A copper-catalyzed synthesis of isothiochromenes and benzo[b]thiophenes via annulation with 1,1,1,3,3,3-hexamethyldisilathiane as a sulfur source is described. The use of the disilathiane as a sulfur source successfully controls the regioselectivity of cyclization to afford high purity products.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Norio Sakai, Kurumi Fukuda, Yohei Ogiwara, Kento Ishida
Summary: Here, an iodide-promoted insertion reaction of vinyltrimethylsilane into diaryl or dialkyl disulfides in the presence of iodine/KF is described, leading to the formation of a 1,1'-adduct, a dithioacetal derivative. This method also enables the insertion into a diaryl diselenide, resulting in the corresponding diselenoacetal derivative.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Physical
Yuriko Ohki, Yohei Ogiwara, Kotohiro Nomura
Summary: Exclusive chemical conversions of polyesters (PEA, PBA, PET, PBT) to the corresponding monomers (diethyl adipate, diethyl terephthalate, ethylene glycol, 1,4-butane diol) by transesterification with ethanol using Cp'TiCl3 catalyst have been demonstrated.
Article
Chemistry, Multidisciplinary
Kento Ishida, Shu Mizusawa, Koji Nakamura, Yohei Ogiwara, Norio Sakai
Summary: The synthesis of 1,3-diarylpropanes is important due to their reported biological activities. Two types of 1,3-diarylpropane derivatives were synthesized through cobalt-catalyzed cycloaddition of 1,6-diynes. The cyclotrimerization of 1,6-diynes catalyzed by CoCl(PPh3)(3) yielded a series of 1,3-diarylpropane derivatives. Additionally, double [4+2]-cycloaddition between 1,6-diynes and 1,3-dienes proceeded in the presence of CoBr2-DPPE-Zn-ZnBr2, followed by oxidation with DDQ to afford another type of 1,3-diarylpropane derivatives.
Article
Chemistry, Multidisciplinary
Yohei Ogiwara, Kotohiro Nomura
Summary: A catalytic method for upcycling polyesters has been developed, which can transform common polyesters into morpholine amides without the use of additives. The method is applicable to various polyesters and allows for further transformations into other organic compounds.
ACS ORGANIC & INORGANIC AU
(2023)
