Article
Chemistry, Applied
I. Lopez-Hernandez, V. Truttmann, N. Barrabes, G. Rupprechter, F. Rey, J. Mengual, A. E. Palomares
Summary: Catalysts based on gold nanoclusters supported by different materials have shown excellent selectivity in the semi-hydrogenation of phenylacetylene to styrene. The interaction between the gold nanoclusters and the support material plays a crucial role in determining the activity and selectivity. Basic support materials enhance both the activity and selectivity.
Article
Chemistry, Physical
Feng Wang, Yuecong Guo, Yutong Zhang, Pingping Tang
Summary: The silver-catalyzed dibromotrifluoromethoxylation of terminal alkynes reported provides 1,1-dibromo-2-(trifluoromethoxy)alkenes in good yields and high regioselectivity under mild reaction conditions. The reaction has a broad substrate scope and can be used for late-stage trifluoromethoxylation of complex small molecules. The products can be further modified, offering a convenient method for synthesizing compounds containing the OCF3 group.
Article
Chemistry, Physical
Qiang Huang, Yu-Xuan Su, Wei Sun, Meng-Yang Hu, Wei-Na Wang, Shou-Fei Zhu
Summary: In this study, an operationally simple and mild iron-catalyzed alkylzincation method for terminal alkynes was developed, which can efficiently produce diverse alkenylzinc compounds with high selectivity. The method demonstrates a high anti-Markovnikov selectivity and high cis stereoselectivity, making it a competitive alternative for the selective synthesis of trisubstituted olefins.
Article
Chemistry, Physical
Lu Ouyang, Yuqiu Liang, Sen Wang, Rui Miao, Jianhua Liao, Zhanhui Yang, Renshi Luo
Summary: Here, we report an efficient one-pot iridium-catalyzed reductive hydroamination of terminal alkynes with amines, which allows for the formation of complex aliphatic amines. This transformation not only employs inexpensive and easily accessible HCO2H as the reducing agent, but also utilizes water as the reaction media, aligning with the principles of green and sustainable chemistry.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Toshimichi Ohmura, Yuta Takaoka, Michinori Suginome
Summary: The copper-catalyzed silafunctionalization of alkynes using silylboronic ester as a silicon source has made rapid progress. The trans-selective 1,2-addition of silylboronic esters to internal arylalkynes was efficiently promoted by the CuOt-Bu/RCy2P/NaOt-Bu catalysts, with a stereochemical switch to cis-addition observed in reactions utilizing Me-2(i-PrO)Si-B(pin) in hydrocarbon solvents including cyclohexane.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Zhen Yang, Rene M. Koenigs
Summary: A conceptually distinct approach was developed for the dicarbofunctionalization of alkynes at room temperature using simple alkyl iodides and a second molecule of alkyne as coupling partner. This method enables the one-step synthesis of 1,3-enynes with high efficiency without the need for exogenous photosensitizers or oxidants, paving the way for cascade reactions via photochemical palladium catalysis.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Multidisciplinary Sciences
Shangwen Fang, Jie Han, Chengjian Zhu, Weipeng Li, Jin Xie
Summary: In this study, a gold-catalyzed, four-component reaction was reported, which efficiently breaks a carbon-carbon triple bond and forms four new chemical bonds, achieving the oxo-arylfluorination or oxo-arylalkenylation of internal aromatic or aliphatic alkynes. The site-directing functional groups in the alkynes control the reaction divergence, with phosphonate unit favoring oxo-arylfluorination and carboxylate motif benefiting oxo-arylalkenylation. The reaction proceeds through an Au(I)/Au(III) redox coupling process using Selectfluor as both an oxidant and a fluorinating reagent, resulting in the synthesis of structurally diverse α,α-disubstituted ketones and tri- or tetra-substituted unsaturated ketones with excellent selectivity and yields.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Hiroki Tashiro, Masahiro Terada, Itaru Nakamura
Summary: Gold-catalyzed reactions were used to synthesize 2H-azirines with sulfenyl and acyl groups at the 3-position, yielding good to excellent results. These reactions involved internal transfer of sulfinyl oxygen atom and carbene insertion into the N-S bond for ring construction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(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
Jieping Chen, Xuzhong Shen, Zhan Lu
Summary: A cobalt-catalyzed Markovnikov-type hydroboration method has been developed for the synthesis of alpha-alkenyl boronates with good regioselectivity and atom economy. The new ligand used with the cobalt hydride catalyst facilitates the selective insertion of terminal alkynes into metal hydride bonds. This protocol shows excellent tolerance to functional groups and delivers valuable alkene derivatives efficiently.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Rakesh K. Saunthwal, Kapil Mohan Saini, Nicolas Grimblat, Abhinandan K. Danodia, Sushil Kumar, Vincent Gandon, Akhilesh K. Verma
Summary: We describe an unconventional approach for the synthesis of highly decorated polyaromatic biaryls with excellent regioselectivity through site-selective Ag-catalyzed twofold electrophilic cycloisomerization followed by Au-catalyzed double C-H activation. DFT computations reveal that this reaction represents a rare example of C1-C5 endo-exo and C1-C6 endo-endo cycloaromatization, with the formation of the 6-membered ring predicted to be the result of an uncommon SEAr on a vinyl carbocation.
Article
Multidisciplinary Sciences
Jieping Chen, Jiale Ying, Zhan Lu
Summary: In this study, a cobalt-catalyzed selective hydroallylation reaction was developed to synthesize branched 1,4-dienes. The reaction exhibited excellent functional group tolerance and substrate scope, allowing for gram-scale reactions. The proposed mechanism was based on deuterium labeling experiment and kinetic studies.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Applied
Jiaming Zhou, Jin Huang, Changhui Lu, Huanfeng Jiang, Liangbin Huang
Summary: A B(C6F5)(3)-catalyzed hydroarylation of terminal alkynes with various phenols at room temperature was developed, leading to the synthesis of 2-gem-vinylphenols with good regio-selectivity. The transformations exhibited a broad substrate scope with moderate yields, and mechanism studies suggested the activation of phenol by B(C6F5)(3) followed by protonation of the alkyne/Friedel-Crafts-type reaction.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Stefan Weber, Daniel Zobernig, Berthold Stoeger, Luis F. Veiros, Karl Kirchner
Summary: The Mn-catalyzed hydroboration of terminal alkenes and the 1,2-diboration of terminal alkynes with pinacolborane have been successfully achieved. The most active pre-catalyst is a bench-stable alkyl bisphosphine Mn-I complex. The catalytic process involves migratory insertion of a CO ligand into the Mn-alkyl bond to yield an acyl intermediate, which further undergoes B-H bond cleavage or C-H bond cleavage for alkenes and alkynes, respectively, forming active Mn-I boryl and acetylide catalysts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Hanna Stachowiak-Dluzynska, Krzysztof Kucinski, Bozena Wyrzykiewicz, Rhett Kempe, Grzegorz Hreczycho
Summary: Vinylsilanes are versatile chemical derivatives that are increasingly being used in various synthetic transformations. In this study, a novel cobalt-catalyzed procedure was developed for the selective hydrosilylation of internal aryl-, alkyl-, and silylalkynes. The use of cobalt complexes with triazine-based PNP pincer-type ligands enabled the exclusive syn-addition of primary and secondary silanes to C=C bonds, resulting in the efficient formation of (E)-silylalkenes and vicinal disilylalkenes with excellent stereoselectivity and regioselectivity. Unlike other transition metal-catalyzed procedures, no external additives were required as hydrosilanes served as both substrates and activators.
Article
Chemistry, Organic
Marios Kidonakis, Manolis Stratakis
Article
Chemistry, Inorganic & Nuclear
Ioannis Titilas, Marios Kidonakis, Charis Gryparis, Manolis Stratakis
Article
Chemistry, Organic
Marios Kidonakis, Manolis Stratakis
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Physical
Iakovos Saridakis, Marios Kidonakis, Manolis Stratakis
Article
Chemistry, Organic
Marios Kidonakis, Manolis Stratakis
Article
Chemistry, Physical
Marios Kidonakis, Manolis Stratakis
Article
Chemistry, Organic
Marios Kidonakis, Anisa Mullaj, Manolis Stratakis
JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Multidisciplinary
Marios Kidonakis, Vasiliki Kotzabasaki, Eleni Vasilikogiannaki, Manolis Stratakis
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Chemistry, Organic
Leandros Zorba, Marios Kidonakis, Iakovos Saridakis, Manolis Stratakis
Article
Chemistry, Organic
Vasiliki Kotzabasaki, Marios Kidonak, Eleni Vassilikogiannaki, Manolis Stratakis
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Applied
Michael Fragkiadakis, Marios Kidonakis, Leandros Zorba, Manolis Stratakis
ADVANCED SYNTHESIS & CATALYSIS
(2020)
Article
Chemistry, Organic
Anastasia Louka, Marios Kidonakis, Iakovos Saridakis, Elisavet-Maria Zantioti-Chatzouda, Manolis Stratakis
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Argyro T. Papastavrou, Marios Kidonakis, Manolis Stratakis, Michael Orfanopoulos
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Marios Kidonakis, Manolis Stratakis
Summary: Supported Au nanoparticles on TiO2 are capable of catalyzing the reduction of alpha-diazocarbonyl compounds into a methylene group in methanol using NH3BH3 or NaBH4. The reaction occurs rapidly at room temperature and differs from the reaction catalyzed by Pt/CeO2, which leads to hydrazones instead. Under stoichiometric Au-catalyzed conditions, ketone-type carbonyls remain intact, in contrast to the uncatalyzed conditions where they are selectively reduced by the boron hydride reagent.
Article
Chemistry, Organic
Marios Kidonakis, Michael Fragkiadakis, Manolis Stratakis
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
