Article
Chemistry, Multidisciplinary
Jun Chen, Yu-Jie Liang, Peng-Zi Wang, Guo-Qing Li, Bin Zhang, Hao Qian, Xiao-Die Huan, Wei Guan, Wen-Jing Xiao, Jia-Rong Chen
Summary: This study presents a photoinduced copper-catalyzed cross-coupling reaction for the generation of allylic esters. The reaction proceeds at room temperature with high regio- and enantioselectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Meredith A. Allen, Myroslava Volosheniuk, Eric A. Nicol, Adrian L. Schwan, Andre M. Beauchemin
Summary: In this study, we report a synthesis of the beta-aminoboronic acid motif through anti-Markovnikov hydroamination reaction, which forms novel BON-containing oxazaborolidine zwitterions. Computational study helps determine the effects of alkene boron substitution, and derivatization reactions support the synthetic utility of the oxazaborolidine adducts.
Article
Chemistry, Multidisciplinary
Mingkai Zhang, Paul S. Lee, Christophe Allais, Robert A. Singer, James P. Morken
Summary: The development of an enantioselective catalytic Suzuki-Miyaura reaction for meso 1,2-diborylcycloalkanes is presented. This reaction provides a modular approach to enantiomerically enriched substituted carbocycles and heterocycles with a versatile boronic ester. With appropriate substrates, compounds containing additional stereogenic centers and fully substituted carbon atoms can be easily synthesized. Preliminary mechanistic experiments suggest that substrate activation is due to the cooperative effect of vicinal boronic esters during the transmetalation step.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Applied
Masami Kuriyama, Genki Maeda, Kazuya Kamata, Yusuke Kodama, Kosuke Yamamoto, Osamu Onomura
Summary: The nickel-catalyzed cross-coupling of bromodifluoromethylphosphonates with arylboron reagents was achieved using a 1,10-phenanthroline-type ligand. Functionalized and heterocycle-containing boroxines were suitable partners for this reaction, and the catalytic modification of biologically active molecules, such as fenofibrate and indomethacin, was successfully accomplished. Moreover, the gram-scale reaction proceeded smoothly with a high yield of desired product.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Javier Teresa, Marina Velado, Roberto Fernandez de la Pradilla, Alma Viso, Blanca Lozano, Mariola Tortosa
Summary: In this work, the catalytic enantioselective cross-coupling of 1,2-bisboronic esters is described. Previous studies on group specific cross coupling have been limited to the use of geminal bis-boronates. This desymmetrization provides a novel approach for preparing enantioenriched cyclopropyl boronates with three contiguous stereocenters, which can be further derivatized through selective functionalization of the carbon-boron bond. Our results suggest that the enantiodetermining step of transmetallation occurs with retention of stereochemistry at carbon.
Article
Chemistry, Organic
Sayan K. Jana, Mamata Maiti, Purusattam Dey, Biplab Maji
Summary: A facile synthesis method for mono-, 1,1-and 1,2-disubstituted cyclopropanes via visible light-mediated photoredox/nickel dual catalysis under mild conditions was demonstrated. Mechanistic inspection and control experiments revealed the importance of dual catalysis and the reaction proceeds via a stepwise oxidative addition followed by an intramolecular S(N)2 reaction.
Article
Chemistry, Organic
Guo-Qing Li, Fan-Rong Meng, Wen-Jing Xiao, Jia-Rong Chen
Summary: Catalytic radical difunctionalization of 1,3-enynes is a promising method for constructing valuable allenes and propargylic compounds. However, there has been limited progress in enantioselective radical 1,2-difunctionalization. In this study, a regio- and enantioselective radical three-component coupling of 1,3-enynes, oxime esters, and carboxylic acids through photoinduced copper catalysis is reported. This protocol demonstrates excellent enantioselectivity and provides access to a library of cyanoalkylated propargylic esters.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Jie Huang, Ling-Ling Chen, Zhi-Min Chen
Summary: A palladium-catalyzed regioselective 1,2-alkynyl-carbonalization of conjugated dienes with ethynylbenziodazolone (EBZ) and indoles has been developed, providing easy access to various molecules containing alkenyl, alkynyl, and indole groups. The resulting products are also suitable for various derivatizations.
Article
Chemistry, Multidisciplinary
Maorui Wang, Chengqian Zhang, Chenggang Ci, Huanfeng Jiang, Pierre. H. Dixneuf, Min Zhang
Summary: Despite the challenges, we have successfully developed a room temperature approach for the direct construction of alpha-hydroxyalkyl cyclic amines through the strategy of electroreductive alpha-hydroxyalkylation. This method offers a broad substrate scope, simplicity in operation, high chemoselectivity, and does not require pressurized H2 gas or transition metal catalysts. The activation of reactants by the zinc ion generated from anode oxidation plays a crucial role in this transformation. This strategy, combined with substrate activation by Lewis acids, is expected to lead to the development of more useful transformations.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Hai-Yang Zhao, Minqi Zhou, Xingang Zhang
Summary: A palladium-catalyzed carbonylative cross-coupling of difluoroalkyl halides with alkyl-9-BBN under 1 atm of CO has been developed, showing broad substrate scope and high functional group tolerance, even towards complex pharmaceuticals. Preliminary mechanistic studies suggest a radical pathway is involved in the reaction.
Review
Chemistry, Multidisciplinary
You Wang, Yuli He, Shaolin Zhu
Summary: Migratory cross-coupling via metal migration is a significant process in academic and industrial fields, providing an attractive alternative for the synthesis of challenging structures. This Account outlines recent progress and developments in the field, including migration-functionalization modes, diverse functionalizations, and strategies for regio- and stereocontrol.
ACCOUNTS OF CHEMICAL RESEARCH
(2023)
Review
Chemistry, Multidisciplinary
Simona Kotesova, Ryan A. Shenvi
Summary: Natural product research requires creative problem-solving ability to explore, understand, and manipulate biological function. By inventing new disconnections and using first-row transition metal-catalyzed cross-coupling methods, it becomes possible to efficiently synthesize complex natural product structures and accelerate the study and evaluation of their biological properties.
ACCOUNTS OF CHEMICAL RESEARCH
(2023)
Article
Chemistry, Organic
Guodong Li, Ke Yu, Jiajun Yang, Bo Xu, Qianjin Chen
Summary: An electrochemical radical strategy involving alkene substrates provides a powerful approach for alkene functionalization. The reaction described in the study enables the synthesis of gem-bisarylthio enamines with good functional group tolerance and high yields, without the need for additional oxidants, transition-metal catalysts, or bases, and can be easily scaled up for gram-scale production.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Chen Zhu, Serik Zhumagazy, Huifeng Yue, Magnus Rueping
Summary: Metal-free C-Se cross-couplings are achieved via the formation of electron-donor-acceptor (EDA) complexes. Visible-light induced reactions are used for the synthesis of unsymmetrical diaryl selenides employing various aryl halides under mild conditions. The scalability of the reaction has been demonstrated, and UV-Vis spectroscopy provides insights into the mechanism.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Shentong Xie, Yuqing Yin, Ya Wang, Jiannan Wang, Xiaoqian He, Ruopeng Bai, Renyi Shi
Summary: The electroreductive cross-electrophile coupling is a powerful, green, and efficient method for constructing challenging C-C bonds, which has attracted increasing attention from organic chemists. Most of the previous works focus on direct two-electrophile cross-coupling. In this work, a nickel-catalyzed three-electrophile electroreductive cross-electrophile coupling has been developed, offering a direct and convergent synthesis to target molecules from easily available and cheap substrates under mild conditions.
Article
Chemistry, Multidisciplinary
Raquel Barroso, Azucena Jimenez, M. Carmen Perez-Aguilar, Maria-Paz Cabal, Carlos Valdes
CHEMICAL COMMUNICATIONS
(2016)
Article
Chemistry, Organic
Miguel Paraja, Carlos Valdes
Article
Chemistry, Organic
Raquel Barroso, Miguel Paraja, Maria-Paz Cabal, Carlos Valdes
Article
Chemistry, Organic
Miguel Paraja, Manuel Plaza, Carlos Valdes
Article
Chemistry, Organic
Raquel Barroso, Maria P. Cabal, Carlos Valdes
SYNTHESIS-STUTTGART
(2017)
Article
Chemistry, Multidisciplinary
Manuel Plaza, Stefano Parisotto, Carlos Valdes
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Article
Chemistry, Organic
Manuel Plaza, Miguel Paraja, Lucia Florentino, Carlos Valdes
Article
Chemistry, Organic
Patricia Fernandez, Carlos Valdes, Francisco J. Fananas, Felix Rodriguez
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Noe Fanjul-Mosteirin, Judith Martin, Carlos Valdes, Carmen Concellon, Vicente del Amo
Review
Chemistry, Multidisciplinary
Helena F. Piedra, Carlos Valdes, Manuel Plaza
Summary: The discovery of new activation modes for carbon-centered radicals, such as photoredox chemistry and low-energy light activation of halogen-bonding adducts, has greatly enriched the field of organic chemistry. These strategies offer more efficient and sustainable ways to generate highly reactive intermediates and enable novel synthetic transformations.
Article
Chemistry, Multidisciplinary
Alvaro Valdes-Maqueda, Lucia Lopez, Manuel Plaza, Carlos Valdes
Summary: The synthesis of benzylboronates from boronic acids and N-tosylhydrazones via photochemical homologation is described. The reaction proceeds through photolysis and carboborylation, successfully avoiding the protodeboronation of benzylboronic acid. The methodology is versatile, allowing for reactions with different ligands and substrates, and can be adapted to continuous flow conditions. The synthetic versatility of boronates enables further transformations, expanding their applications.
Article
Chemistry, Multidisciplinary
Helena F. Piedra, Victoria Gebler, Carlos Valdes, Manuel Plaza
Summary: In this study, a facile and general synthetic method for the preparation of novel S-alkenyl and dienyl phosphoro(di)thioates was presented for the first time. Mechanistic investigations revealed that the reactions rely on the photochemical excitation of a halogen-bonding complex and follow a radical-based pathway. This method showed a broad substrate scope and high functional group tolerance, including molecules derived from natural products with potential unknown biological properties. Additionally, an efficient continuous flow protocol was developed for the upscale of these reactions.
Article
Chemistry, Organic
Raquel Barroso, Maria-Paz Cabal, Azucena Jimenez, Carlos Valdes
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
Article
Chemistry, Applied
Miguel Paraja, Raquel Barroso, M. Paz Cabal, Carlos Valdes
ADVANCED SYNTHESIS & CATALYSIS
(2017)
Article
Chemistry, Multidisciplinary
Lucia Lopez, Maria-Paz Cabal, Carlos Valdes
Summary: The study shows that the reactions of N-sulforlythydrazones derived from cyclic ketones with azidopropylboronic acid and azidomethylplienylboronic acid can produce spirocyclic compounds without the need for transition-metal catalysts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
