Review
Chemistry, Multidisciplinary
Brock E. Leland, Joydeb Mondal, Ryan J. Trovitch
Summary: This article explores the historical and recent efforts in catalyzing the dehydrocoupling of amines and silanes, a direct method for Si-N bond formation with hydrogen as a byproduct. The advantages of this transformation have driven the development of catalysts across the periodic table, leading to advances in efficiency and selectivity. The article highlights the formation of monomeric, oligomeric, and polymeric aminosilanes separately, and features a recent study on the manganese-catalyzed synthesis of perhydropolysilazane and commercial chemical vapor deposition precursors.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Florian Puls, Philipp Linke, Olga Kataeva, Hans-Joachim Knoelker
Summary: This paper describes a convenient method for the oxidation of olefins to ketones using Fe(dbm)(3) or a combination of iron(II) chloride and neocuproine as catalysts and phenylsilane as an additive. The reactions are efficient and have a high yield and selectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Yanyan Liao, Shunmin Zhang, Xuefeng Jiang
Summary: Thioamide peptides were synthesized in a one-pot process by linking natural amino acids in the presence of thiolphosphonate and trichlorosilane, with minimal racemization. Experimental and computational studies showed that trichlorosilane enables the activation of carboxylic acids and coupling with thiolphosphonate to obtain the intermediate S-acyl dithiophosphate. Silyl-activated quadrangular metathesis transition states resulted in the formation of thioamide peptides.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Michael S. Crocker, Zihang Deng, Jeffrey N. Johnston
Summary: Amide synthesis is widely used in drug development and peptide synthesis, but waste elimination in this process has had limited success. Umpolung amide synthesis has been developed as a method for enantioselective synthesis, but it cannot forge N-aryl amides. This study presents a direct synthesis method for N-aryl amides using a simple Bronsted base as a promoter, using alpha-fluoronitroalkanes and N-aryl hydroxyl amines.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Wanyao Zheng, Yongjie Xu, Hang Luo, Yunhui Feng, Jinqiao Zhang, Luqing Lin
Summary: In this study, we have reported a light-promoted dual catalysis for arylsilylation of alkenes via radical-radical cross-coupling with various hydrosilanes. This method provides a simple and efficient way to prepare organosilicon compounds with a wide range of substrates and good tolerance towards functional groups under transition-metal- and chemical-oxidant-free conditions. Additionally, the arylsilylation of alkenes can also proceed via a possible electron donor-acceptor complex under exogenous photocatalyst-free conditions.
Article
Chemistry, Physical
Gabriel Durin, Jean-Claude Berthet, Emmanuel Nicolas, Thibault Cantat
Summary: Efficient synthesis of hydrosilanes was achieved by catalytic hydrogenolysis of chlorosilanes using an iridium (III) pincer catalyst. A careful selection of nitrogen base allowed for high yields (up to 98%) of Me3SiH, Et3SiH, and Me2SiHCl directly from their corresponding chlorosilanes.
Article
Chemistry, Organic
Wataru Muramatsu, Hisashi Yamamoto
Summary: We describe the development of a reliable catalytic protocol for peptide bond formation that is generally applicable to natural and unnatural alpha-amino acids, beta-amino acids, and peptides bearing various functional groups. A 10 mol % loading of HSi[OCH(CF3)(2)](3) as a catalyst was sufficient to guarantee a consistently high yield of the resulting peptide. This method facilitates the sustainable utilization of natural resources by using a catalyst and an auxiliary based on earth-abundant silicon.
Article
Chemistry, Applied
Nadja E. Niggli, Tobias Vollgraff, Christian Winter, Desislava Slavcheva Petkova, Stefan Benson, Roland Goetz, A. Stephen K. Hashmi, Thomas Schaub
Summary: In this study, we report an aminolysis reaction of aromatic and alkyl esters with anilines catalyzed by a readily available catalytic system comprising of an earth-abundant Mn-salt in combination with an inexpensive base.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Shanxuan Wu, Zijun Huang, Xiaolin Jiang, Fachao Yan, Yuehui Li, Chen-Xia Du
Summary: An efficient method using oxofluorovanadates as catalysts has been developed for the reductive amination of CO2, resulting in the transformation of various amines into N-formylated products in moderate to excellent yields at room temperature in the presence of phenylsilane. Mechanistic studies indicate a reaction pathway initiated through F-Si interactions, with activated phenylsilane allowing for CO2 insertion and subsequent formation of the target product through amine attack.
Article
Chemistry, Multidisciplinary
Gabriel Durin, Albane Fontaine, Jean-Claude Berthet, Emmanuel Nicolas, Pierre Thuery, Thibault Cantat
Summary: The metal-free catalytic hydrogenolysis of silyl triflates and halides to hydrosilanes is achieved using arylborane Lewis acids as catalysts. The catalyst acts as a Frustrated Lewis Pair and is able to split H-2 and generate a boron hydride intermediate capable of reducing (pseudo)halosilanes. This metal-free organocatalytic system competes with metal-based catalysts and enables the formation of a variety of hydrosilanes at room temperature in high yields under low hydrogen pressure.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Giulio Valenti, Paul Tinnemans, Iaroslav Baglai, Willem L. Noorduin, Bernard Kaptein, Michel Leeman, Joop H. ter Horst, Richard M. Kellogg
Summary: An efficient method for deracemization of a racemate to the desired (R)-enantiomer of Praziquantel has been developed by coupling incompatible racemization and crystallization processes. Through a library approach, a derivative that crystallizes as a conglomerate has been identified, and using a flow system, the incompatible processes have been combined to achieve complete deracemization to the desired (R)-enantiomer.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Cong Luo, Yang Zhou, Hang Chen, Ting Wang, Zheng-Bing Zhang, Pan Han, Lin-Hai Jing
Summary: We have developed an efficient strategy that combines organic photoredox and hydrogen atom transfer to prepare gem-difluoroallylsilanes via defluorinative silylation of alpha-trifluoromethylstyrenes using hydrosilanes as silicon sources. This environmentally friendly approach allows for the preparation of structurally diverse gem-difluoroallylsilanes with excellent functional group compatibility, making it suitable for late-stage modification of bioactive and complex molecules.
Article
Chemistry, Organic
Yves Yeboue, Marion Jean, Gilles Subra, Jean Martinez, Frederic Lamaty, Thomas-Xavier Metro
Summary: Peptides can be produced in high yields with minimal epimerization through mechanochemical coupling of peptide fragments containing highly epimerization-prone and/or highly hindered amino acids at the C-terminus, with ball milling identified as the key element enabling such results.
Article
Microbiology
Reyhane Nikookar Golestani, Elahe Ghods, Mosayeb Rostamian, Hamid Madanchi, Ahmad Farhad Talebi
Summary: This study synthesized acylated and amidated derivatives of AurH1 antifungal peptide and investigated their antifungal activity and cytotoxicity. The results showed that amidation at the C-terminal of AurH1 can improve its antifungal properties and cytotoxicity compared to acylation at the N-terminal. Moreover, amidation of the C-terminal does not affect the mechanism of action and time of killing of AurH1.
Review
Chemistry, Multidisciplinary
Joachim F. R. Van Guyse, Yann Bernhard, Annelore Podevyn, Richard Hoogenboom
Summary: Non-activated esters have prominent features in polymer science but their low reactivity prevents their direct use in post-polymerization modification. However, utilizing non-activated esters for modification is still a valuable opportunity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Erika Nakashima, Hisashi Yamamoto
CHEMISTRY-AN ASIAN JOURNAL
(2017)
Review
Biochemistry & Molecular Biology
Wataru Muramatsu
TRENDS IN GLYCOSCIENCE AND GLYCOTECHNOLOGY
(2016)
Article
Chemistry, Multidisciplinary
Erika Nakashima, Hisashi Yamamoto
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Article
Chemistry, Physical
Wataru Muramatsu, Hiroaki Tsuji, Hisashi Yamamoto
Article
Chemistry, Multidisciplinary
Wataru Muramatsu, Tomohiro Hattori, Hisashi Yamamoto
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2019)
Article
Chemistry, Multidisciplinary
Wataru Muramatsu, Hisashi Yamamoto
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2019)
Review
Chemistry, Multidisciplinary
Wataru Muramatsu, Tomohiro Hattori, Hisashi Yamamoto
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2020)
Article
Polymer Science
Yoshifumi Hosokawa, Erika Nakashima, Tomonaga Ueno
Summary: This study analyzed the combustion process of polymers with different molecular weights in the vertical flame test through image analysis, revealing two stages in the combustion process and significant effects of molecular structure or molecular weight on flame characteristics and combustion behavior.
JOURNAL OF APPLIED POLYMER SCIENCE
(2021)
Article
Chemistry, Multidisciplinary
Wataru Muramatsu, Hisashi Yamamoto
Summary: A one-pot peptide bond-forming reaction has been developed using unprotected amino acids and peptides, with the help of two different silylating reagents and catalysts. This method is versatile, providing high yields of corresponding peptides without racemization or polymerization.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Erika Nakashima, Hisashi Yamamoto
Summary: This study introduces two methods for the formation of 2-4 peptide bonds using a mild Bronsted acid under mild conditions. One of the methods has been successfully adapted to flow synthesis at room temperature. This solvent-free method allows for efficient formation of dipeptide, tripeptide, and tetrapeptide bonds at ambient temperature. This study also proposes a new production method to overcome the limitations of scale-up production.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Wataru Muramatsu, Hisashi Yamamoto
Summary: We describe the development of a reliable catalytic protocol for peptide bond formation that is generally applicable to natural and unnatural alpha-amino acids, beta-amino acids, and peptides bearing various functional groups. A 10 mol % loading of HSi[OCH(CF3)(2)](3) as a catalyst was sufficient to guarantee a consistently high yield of the resulting peptide. This method facilitates the sustainable utilization of natural resources by using a catalyst and an auxiliary based on earth-abundant silicon.
Article
Chemistry, Multidisciplinary
Wataru Muramatsu, Hisashi Yamamoto
Summary: An economical, solvent-free, and metal-free method for peptide synthesis via C-N bond cleavage using lactams has been developed, which exhibits high atom economy and can tolerate side chains bearing a range of functional groups, affording up to >99% yields of the corresponding peptides.
Review
Chemistry, Multidisciplinary
Wataru Muramatsu, Tomohiro Hattori, Hisashi Yamamoto
Summary: The article discusses the development of methods for amide bond formation without typical condensation reagents, presenting a metal-templated macrolactamisation approach that addresses long-standing challenges in peptide chemistry through substrate control.
CHEMICAL COMMUNICATIONS
(2021)