Article
Chemistry, Multidisciplinary
Josep Mas-Rosello, Christopher J. Cope, Eric Tan, Benjamin Pinson, Alan Robinson, Tomas Smejkal, Nicolai Cramer
Summary: Cyclometalated cyclopentadienyl iridium(III) complexes are efficient catalysts in the hydrogenation of oximes, with alkoxy-substituted aryl ketimine ligands providing the best catalytic performance. The stable iridium C,N-chelation is crucial for the catalytic activity, and the hydrogenation system demonstrates high functional group compatibility.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Inorganic & Nuclear
Juan Carlos Perez-Sanchez, Raquel P. Herrera, M. Concepcion Gimeno
Summary: This review explores the recent advancements in the combination of the ferrocene structure with gold-mediated catalysis in the field of organometallic chemistry, discussing the application and potential of ferrocene in gold catalysis.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Callum R. Woof, Derek J. Durand, Natalie Fey, Emma Richards, Ruth L. Webster
Summary: The catalytic mechanism of iron-catalyzed alkene isomerization reaction was studied through a combination of experimental and theoretical approaches. The results suggest that the isomerization of alkenes can be achieved through the combination of a hydride source and an iron(II) beta-diketiminate pre-catalyst.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Teng Yuan, Qi Tang, Chuan Shan, Xiaohan Ye, Jin Wang, Pengyi Zhao, Lukasz Wojtas, Nicholas Hadler, Hao Chen, Xiaodong Shi
Summary: This study presents a novel method for alkyne trifunctionalization through gold catalysis, achieving consecutive reactions with high efficiency and excellent yields under mild conditions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Xiaohan Ye, Chenhuan Wang, Shuyao Zhang, Qi Tang, Lukasz Wojtas, Minyong Li, Xiaodong Shi
Summary: This study achieved enantioselective, intermolecular alkene arylamination through gold redox catalysis. Chiral P,N ligands were found to be the optimal choice, enabling alkene aminoarylation with good yields and excellent stereoselectivity. As the first example of enantioselective gold redox catalysis, this work confirmed the feasibility of applying a chiral ligand at the gold(I) stage and introduced a new way to conduct gold redox catalysis with stereochemistry control.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Review
Chemistry, Multidisciplinary
Catriona C. James, Bas de Bruin, Joost N. H. Reek
Summary: The importance of transition metal catalysis lies in its wide range of applications, including the synthesis of chemicals, natural products, and pharmaceuticals. However, a relatively new application is the catalysis of new-to-nature reactions inside living cells. The complex environment of living cells poses challenges to transition metal catalysts due to the potential inhibition or deactivation by various biological components. In this review, we summarize the current progress in the field of transition metal catalysis, focusing on the evaluation of catalysis efficiency under living cell and biological conditions. Catalyst poisoning is a common issue in this field, and we suggest that future research should explore physical and kinetic protection strategies to enhance the reactivity of catalysts in cells.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Tingrui Li, Yilitabaier Julaiti, Xiaopeng Wu, Jie Han, Jin Xie
Summary: The gold-catalyzed ring-opening rearrangement of cyclopropenes provides an efficient method for synthesizing polysubstituted naphthols or aryl-substituted furans. The reaction selectivity between naphthols and furans can be switched by using different gold-carbenes or gold-carbocations as catalysts.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Cristian Cavedon, Sebastian Gisbertz, Susanne Reischauer, Sarah Vogl, Eric Sperlich, John H. Burke, Rachel F. Wallick, Stefanie Schrottke, Wei-Hsin Hsu, Lucia Anghileri, Yannik Pfeifer, Noah Richter, Christian Teutloff, Henrike Mueller-Werkmeister, Dario Cambie, Peter H. Seeberger, Josh Vura-Weis, Renske M. van der Veen, Arne Thomas, Bartholomaus Pieber
Summary: We demonstrate visible-light-mediated carbon-heteroatom cross-coupling reactions using a photoactive Ni(II) precatalyst. The activation of this precatalyst involves an initial intraligand charge transfer event triggered by visible light irradiation. Additionally, a porous, recyclable organic polymer for heterogeneous nickel catalysis of cross-coupling reactions is obtained through ligand polymerization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Philipp M. Stein, Matthias Rudolph, A. Stephen K. Hashmi
Summary: Water has an impact on the rate constant of gold-catalyzed reactions, not only showing tolerance but also potentially promoting reactions in some cases. Kinetic data demonstrates that the addition of water in gold catalysis can lead to better results.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Guilin Ruan, Pritam Ghosh, Natalia Fridman, Galia Maayan
Summary: Water electrolysis is a promising method for producing low-cost renewable fuels, but the efficiency is limited by high overpotential and slow kinetics. Cu-2(BEE)(2) is a unique homogeneous electrocatalyst for water oxidation, with low overpotential and a high turnover frequency. The ethanolic side chains and the borate buffer play significant roles in the high stability and catalytic activity of Cu-2(BEE)(2).
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Shashank P. Sancheti, Yukta Singh, Manoj V. Mane, Nitin T. Patil
Summary: This study reports the first gold-catalyzed 1,2-dicarbofunctionalization of alkynes using organohalides as non-prefunctionalized coupling partners. The mechanism of the reaction involves an oxidative addition/pi-activation pathway, which is different from the migratory insertion/cis-trans isomerization pathway observed in other transition metal catalysis. Mechanistic investigations including experiments, NMR studies, HR-MSMS analyses, and DFT calculations provide strong support for the proposed mechanism.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Jonathan Trouve, Paolo Zardi, Shaymaa Al-Shehimy, Thierry Roisnel, Rafael Gramage-Doria
Summary: Utilizing secondary interactions between substrates and catalysts is a promising approach to discover selective transition metal catalysts for atom-economy C-H bond functionalization. The most powerful catalysts are often discovered through trial-and-error screening, as small stereo-electronic modifications within the substrate and catalyst can lead to vastly different reactivities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Vishal Chugh, Basujit Chatterjee, Wei-Chieh Chang, Hanna H. Cramer, Carsten Hindemith, Helena Randel, Thomas Weyhermueller, Christophe Fares, Christophe Werle
Summary: An adaptive catalytic system that controls the nitroarene hydrogenation network has been developed for the synthesis of aniline and hydroxylamine derivatives. The system shows high chemoselectivity and is applicable at a preparative scale.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Yanwei Cao, Yang Huang, Lin He
Summary: In this study, a step- and atom-economic synthesis of N-Boc amines from readily available substrates was reported. The catalytic system showed unique selectivity for N-Boc amines in good yields and demonstrated potential application prospects in industrial syntheses. Mechanistic investigations revealed that gold catalyzed the reaction and copper acted as an electron transfer mediator in the catalytic cycle.
Article
Chemistry, Applied
Fernando Martinez-Lara, Anisley Suarez, Noelia Velasco, Samuel Suarez-Pantiga, Roberto Sanz
Summary: The gold-catalyzed transformation of propargylic glycols with thiols results in the formation of alpha-indol-3-yl alpha-((Z)-2-thioalkenyl) ketones through a complex but selective reaction mechanism. This sequence involves regioselective thiolation of indolyl diols followed by the attack of sulfur on the activated alkyne, rather than the indole. The final compounds are obtained in high yields from simple starting materials such as indolyl acyloins, ethynyl magnesium bromide, and thiols.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Review
Chemistry, Organic
Dilip V. Patil, Seunghoon Shin
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Nguyen H. Nguyen, Quynh H. Nguyen, Soumen Biswas, Dilip V. Patil, Seunghoon Shin
Article
Chemistry, Organic
Tae-Woong Urn, Girim Lee, Seunghoon Shin
Article
Chemistry, Organic
Jangbin Im, Sang Ik Shin, Cheon-Gyu Cho, Seunghoon Shin
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Cheng-dong Wang, Qinyang Chen, Seunghoon Shin, Cheon-Gyu Cho
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Subin Choi, Hyeonji Oh, Jeongwoo Sim, Eunsoo Yu, Seunghoon Shin, Cheol-Min Park
Article
Chemistry, Multidisciplinary
Hanbyul Kim, Jiwon Jang, Seunghoon Shin
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Multidisciplinary
Ravi Kumar, Quynh H. Nguyen, Tae-Woong Um, Seunghoon Shin
Summary: Umpolung approach, achieved through polarity inversion of traditional enolates, provides an unprecedented opportunity for cross-coupling via alkylation. This method allows for coupling with unmodified nucleophiles under conditions that avoid the highly basic nature required in classical enolate chemistry.
Article
Chemistry, Multidisciplinary
Nguyen H. Nguyen, Soo Min Oh, Cheol-Min Park, Seunghoon Shin
Summary: The study presents a strategy to invert the normal polarity of indoles in heterobiaryl coupling, achieving exclusive ortho-selective coupling with phenols. Various substrates coupled with exceptional efficiency and selectivity under the action of Brønsted acid or Cu(i) catalysts at ambient temperature.
Article
Chemistry, Organic
Milan Bera, Ho Seong Hwang, Tae-Woong Um, Soo Min Oh, Seunghoon Shin, Eun Jin Cho
Summary: A new type of sp(3)-like N-centered radical was generated through selective energy transfer catalysis, which led to the synthesis of valuable 3-oxyindole derivatives.
Article
Chemistry, Physical
Quynh H. Nguyen, Ho Seong Hwang, Eun Jin Cho, Seunghoon Shin
Summary: Irradiation of N-enoxybenzotriazoles with blue LEDs in the presence of photosensitizers generates benzotriazolyl and alpha-carbonyl radicals, leading to the synthesis of biologically significant benzotriazolyl derivatives through atom-economic [1,3]-shift and group transfer radical addition reactions.
Article
Chemistry, Organic
Jiwon Jang, Youngjin Bae, Seunghoon Shin
Summary: The gold-catalyzed formation of allyl sulfonium intermediates enables an exceptional level of control for the synthesis of skipped 1,4-dienes. However, the use of cinnamyl thioether derivatives in this reaction has been unsuccessful due to the dissociation of the cinnamyl cation. By tuning the bisphosphine ligands, cinnamyl thioethers can be successfully engaged in the rearrangement to yield the desired 1,4-dienes in good yields and with high enantioselectivity. The resulting products can be further transformed into optically active molecules.
Article
Chemistry, Organic
Eun-Jeong Kwahk, Nguyen H. Nguyen, Sumin Jang, Seunghoon Shin, Hyunwoo Kim
Summary: In this study, we propose a new method for chiral recognition of phosphates using cationic octahedral cobalt complexes. By utilizing 31P NMR spectroscopy, we accurately measure the enantiopurities of chiral phosphoric acids after forming ion pairs with the cobalt complexes. This method has been successfully applied to various chiral phosphoric acids and achieved an optical resolution with an enantiomeric excess of greater than 99%.
Article
Chemistry, Organic
Jiwon Jang, Hanbyul Kim, Seunghoon Shin
Summary: This study reports a revised mechanism for the gold-catalyzed enantioselective thioallylation of propiolates, which delivers highly enantio-enriched alpha-allyl-beta-thioacrylates. The research reveals that the competitive binding of thioethers as nucleophiles to the catalytic site inhibits its activity. The revised mechanism suggests that the conjugate addition of thioethers is the slowest step, followed by a rapid rearrangement, indicating the efficacy of the sulfonium-based approach in accelerating Claisen rearrangement.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Quynh H. Nguyen, Nguyen H. Nguyen, Hanbyul Kim, Seunghoon Shin
