Article
Chemistry, Multidisciplinary
Haibo Zhu, Yingying Zhang, Gaowen Ren, Yaoqi Wang, Jia Meng, Qiangwen Fan, Zongbo Xie, Zhang-Gao Le
Summary: An efficient nickel-catalyzed cross-coupling reaction for the synthesis of 2-sulfonylthiazoles from readily available 2-chlorobenzothiazoles and sodium sulfinates has been developed. The reaction proceeds smoothly at room temperature, allowing for the successful coupling of diverse substitution patterns. The use of precious catalysts and sensitive ligands is avoided, resulting in moderate to excellent yields of various 2-sulfonylthiazoles.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Applied
Divya Bhatt, Hun Young Kim, Kyungsoo Oh
Summary: In this study, the synthesis of 3-sulfonyl furans was achieved by the addition of sodium sulfinate to (E)-beta-chlorovinyl ketones, followed by the aerobic cyclization of alkenyl sulfone intermediates. The optimal catalyst system for the cyclization was identified as Cu(OTf)(2), with molecular oxygen as the terminal oxidant. This strategy allows the synthesis of highly functionalized and substituted furan derivatives.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Yong Liu, Shuya Xing, Jing Zhang, Wen Liu, Yuenian Xu, Yan Zhang, Kefang Yang, Lei Yang, Kezhi Jiang, Xinxin Shao
Summary: A nickel-catalyzed reductive cross coupling method for generating unsymmetrical thioethers from organic iodides, thiosulfonates, and selenosulfonates under mild conditions with low catalyst loading was developed. The approach features good functional group tolerance, excellent chemo-selectivity, and diverse synthetic applications including late-stage pharmaceutical modifications and preparation of various targeted compounds. Primary mechanistic studies suggested a radical pathway and demonstrated the ability to form C-S/C-Se bonds under mild reaction conditions.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Qian Wang, An Liu, Yan Wang, Chuanfa Ni, Jinbo Hu
Summary: The copper-mediated cross-coupling reaction between a diazo compound and a sodium alkane(arene)sulfinate results in the formation of a sulfone product. The effectiveness of the sulfinates in this reaction is determined by their nucleophilicity.
Article
Chemistry, Multidisciplinary
Ge Wu, Xueying Zhou, Caihong Wang
Summary: A novel and efficient method for decarboxylative alkynylselenation of indoles using Se powder and propiolic acids as catalyst has been developed. This method avoids the use of prefabricated arylselenation reagent and over-seleniumation issues and enriches the chemistry of selenium powder. Furthermore, this reaction can be extended to pyrrole, and its practical utility has been demonstrated in gram-scale synthesis and late-stage indolylselenation of Clofibrate-derived propiolic acid.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Meng-Die Li, Zi-Han Wang, Hui Zhu, Xin-Ru Wang, Jia-Run Wang, Tao-Yan Lin
Summary: In this study, the first remote enantioselective copper-catalyzed sulfonylation of yne-allylic esters with sodium sulfinates was reported. The method demonstrated practicality and attractiveness due to the use of readily available starting materials, mild reaction conditions, excellent selectivity, and broad substrate scope.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Xinlan A. F. Cook, Loic R. E. Pantaine, David C. Blakemore, Ian B. Moses, Neal W. Sach, Andre Shavnya, Michael C. Willis
Summary: Heteroaromatic sulfinates are effective nucleophilic reagents in Pd-0-catalyzed cross-coupling reactions with aryl halides. Base-activated, latent sulfinate reagents, such as beta-nitrile and beta-ester sulfones, have been introduced to address challenges in purifying and solubilizing metal sulfinate salts, as well as their tolerance to multi-step transformations. These latent sulfinate reagents have proven to be stable through multi-step substrate elaboration and amenable to scale-up processes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Junyi Jin, Kaiyang Zhou, Xinxiang Liu, Can Wang, Yunfeng Chen
Summary: A direct C-H bond oxidative sulfonylation of beta-alkyl cyanoalkenes with sodium sulfinates was achieved using a copper salt catalyst, I-2 and DMSO as the oxidative system. This reaction provides a straightforward and practical approach to synthesizing various cyanoallylic sulfones.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Lulu Si, Biquan Xiong, Shipan Xu, Longzhi Zhu, Yu Liu, Weifeng Xu, Ke-Wen Tang
Summary: A copper-catalyzed cross-dehydrogenative coupling reaction of P(O)-H compounds with O-/S-nucleophiles has been developed for the synthesis of phosphinates and phosphinothioates. The reaction tolerates a wide range of O- and S-nucleophiles, giving good to excellent yields of the target products. The protocol is effective and convenient, using inexpensive copper iodide as the catalyst and avoiding the use of hazardous and toxic reagents. Through control and competitive experiments, a plausible reaction mechanism has been proposed, suggesting a radical process.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Qing Wang, Xiangzhang Tao, Shengyang Ni, Yi Pan, Yi Wang
Summary: Bimolecular nucleophilic substitution S(N)2 is the earliest and most important means of amination of alkyl electrophiles, but its practical utilization is mostly limited to primary or activated substrates. Establishing C(sp(3))-N bonds from alkyl substrates in cross-coupling chemistry using palladium and nickel catalysts has been a persistent challenge. The existing routes are restricted to copper catalysis and photoredox catalysis. In this study, we demonstrate an alternative amination strategy that rapidly constructs C(sp(3))-N bonds from accessible alkyl electrophiles by utilizing Nickel (III) species reductive eliminations under high efficiency catalysis.
Article
Chemistry, Organic
Shuai Zhong, Zhiwei Zhou, Feng Zhao, Guojiang Mao, Guo-Jun Deng, Huawen Huang
Summary: In this study, sulfinates were successfully used as sulfenylating reagents in C-S couplings through visible-light-induced photo/nickel dual catalysis under base- and external reductant-free conditions. The method showed high selectivity and tolerance towards various functionalities.
Review
Chemistry, Multidisciplinary
Irina P. Beletskaya, Valentine P. Ananikov
Summary: In this review, recent progress in C-Z bond formation reactions (Z = S, Se, Te) catalyzed by transition metals is discussed. Two complementary methodologies, catalytic cross-coupling reactions and catalytic addition reactions, are considered. The development of advanced catalytic systems aims at improving catalyst efficiency, reducing catalyst loading, achieving better cost efficiency, addressing environmental concerns, and increasing selectivity and yields. The importance of research efforts in sustainability and green chemistry areas is critically assessed. Mechanistic studies are highlighted as crucial for the development of new catalytic systems and the key achievements, problems, and challenges in this field are summarized.
Article
Materials Science, Multidisciplinary
Elkana Rugut, Daniel Joubert, Glenn Jones
Summary: This study evaluates the structural stability, lattice thermal conductivity, transport properties, and thermoelectric figure of merit of scandium copper chalcogenides based on first principles. By exploring transport properties and thermal conductivity, the study reveals that scandium copper chalcogenides show promising potential for thermoelectric applications. Additionally, among the three ternary compounds, ScCuSe2 exhibits the highest dimensionless figure of merit at high temperatures.
MATERIALS TODAY COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Yang Wang, Feng Zhang, Yi Wang, Yi Pan
Summary: This work describes an electrochemical enabled nickel-catalyzed chemoselective C-S bond coupling protocol for the production of aryl sulfides and sulfones. By simply switching the nickel catalysts and electrodes, this electrochemical C-S bond coupling has demonstrated excellent redox activity, scalability, and sustainability. Furthermore, the mechanism for this electrochemical cross-coupling reaction has been investigated.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Inorganic & Nuclear
Angelita M. Barcellos, Manoela Sacramento, Gabriel P. da Costa, Gelson Perin, Eder Joao Lenardao, Diego Alves
Summary: Organochalcogen compounds have significant synthetic and biological applications. The coupling reaction between boronic acids, borate anions or boronic esters with different sources of chalcogen mediated by transition metals is a powerful tool for the formation of functionalized diorganyl chalcogenides. This strategy allows for the preparation of selenides, sulfides, and tellurides with high complexity and molecular diversity in good to excellent yields.
COORDINATION CHEMISTRY REVIEWS
(2021)
Article
Chemistry, Organic
Nobukazu Taniguchi
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Nobukazu Taniguchi
Article
Chemistry, Organic
Nobukazu Taniguchi
Article
Chemistry, Organic
Nobukazu Taniguchi
Article
Chemistry, Multidisciplinary
Nobukazu Taniguchi
Article
Chemistry, Organic
Nobukazu Taniguchi, Kenji Kitayama
Article
Chemistry, Inorganic & Nuclear
Nobukazu Taniguchi, Kenji Kitayama
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
(2019)
Article
Chemistry, Organic
Nobukazu Taniguchi, Kenji Kitayama
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Nobukazu Taniguchi
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Nobukazu Taniguchi
Summary: A copper-catalyzed hydroxysulfenylation of alkenes using disulfides in the presence of n-Bu4NI and H2O is reported in this article. The reaction proceeded smoothly under air atmosphere and resulted in good yields of β-hydroxysulfides with regio- and anti-selectivity. Additionally, the reaction using diselenides also provided the desired β-hydroxyselenides effectively. The chalcogenide groups on dichalcogenides were utilized in these reactions. Furthermore, the procedure was successful for hydrosulfenylation using thiols.
Article
Chemistry, Organic
Nobukazu Taniguchi, Kenji Kitayama
Summary: This article describes a convenient regioselective introduction of sulfide groups to alkenes or alkynes using metal catalysis, which has important applications in organic synthesis.
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
(2022)
Article
Chemistry, Organic
Nobukazu Taniguchi
Summary: Znl(2)-catalyzed addition of ammonium thiocyanate to olefins in the presence of 4-toluenesulfonic acid and tetrabutylammonium iodide has been developed, providing isothiocyanates selectively and in good yields through a Markovnikov-type process and a radical isomerization.
Article
Chemistry, Organic
Nobukazu Taniguchi, Kenji Kitayama
Summary: In this study, the Mo-catalyzed hydroarylation of alkenes at room temperature was explored. The procedure showed good regioselectivity in obtaining a mixture of para- and ortho-isomers with a high yield using electron rich arenes. Furthermore, the reaction of allylic acetates was also investigated, resulting in the formation of allyl arenes through the leaving of acetoxy group.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Nobukazu Taniguchi, Mamoru Hyodo, Lin-Wei Pan, Ilhyong Ryu
Summary: Site-selective C(sp(3))-H thiolation has been achieved using thiosulfonates as substrates and the decatungstate anion as a photocatalyst. The reaction proceeds through a cascade of double S(H)2 reactions, HAT and ArS group transfer, and PCET, allowing the recovery of the catalyst, W10O324-.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Nobukazu Taniguchi
Summary: Zn-catalyzed reactions of alkenes with alkyl thiols afford Markovnikov-type alkyl sulfides, while Zn(OAc)(2)-catalyzed reactions give rise to anti-Markovnikov-type products, proceeding via a radical process.
