Article
Chemistry, Multidisciplinary
Kun Liu, Zhe Wang, Augustinus N. Kuenzel, Marcus Layh, Armido Studer
Summary: We report a formal intermolecular beta-C-C bond formation reaction of a broad range of aldehydes and ketones with different allyl electrophiles through cooperative nickel and photoredox catalysis. The transformation features mild conditions, excellent regioselectivity, wide functional group tolerance, and high reaction efficiency. This method provides a facile and regioselective approach to beta-allylation of carbonyl compounds, enabling the preparation of valuable building blocks that are difficult to access using existing methodology.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Yanfang Han, Long Zhang, Sanzhong Luo
Summary: A highly diastereo- and enantioselective retro-Claisen reaction has been developed using chiral primary amine catalysis. This reaction enables efficient synthesis of chiral beta,beta-diaryl-alpha-branched ketones with excellent stereoselectivities. The reaction proceeds through a tandem sequence involving benzylic C-C bond formation, C-C bond cleavage, and stereospecific enamine protonation. The use of o-quinone methides as diaryl precursors allows for a broad substrate scope, mild reaction conditions, and a high degree of stereocontrol.
Article
Chemistry, Organic
Rodney A. Fernandes, Naveen Chandra, Ashvin J. Gangani, Gulenur N. Khatun
Summary: An efficient method for the synthesis of (E)-(3-alkoxybut-1-enyl)benzenes has been developed via Pd-catalyzed regioselective intermolecular hydroalkoxylation of 1-arylbutadienes. This method offers a simple operation, without the need for dry reaction conditions, and shows good tolerance to various substrates. The presence of chloromethyl methyl ether (MOMCl) as an additive is crucial to the success of the reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Zhili Liu, Lianfen Chen, Dong Zhu, Shifa Zhu
Summary: A highly efficient formal allylation of dihydronaphthotriazoles with alkenes under rhodium(II) catalysis is reported. Various allyl dihydronaphthalene derivatives were obtained with moderate to good yields and excellent chemoselectivity through rhodium(II) azavinyl carbenes. Notably, the allylic C(sp(2))-H activation occurs instead of the traditional C(sp(3))-H activation in the formal allylation process, and good to excellent enantioselectivities are achieved when monosubstituted alkenes are used.
Article
Chemistry, Physical
Bing Zhang, Xueying Guo, Lei Tao, Ruolin Li, Zhenyang Lin, Wanxiang Zhao
Summary: The deoxygenative reduction of 1,3-diketones using a rhodium-catalyzed method exhibits high regioselectivity toward aliphatic carbonyl reduction, good functional group tolerance, and potential in the late-stage modification and synthesis of natural products and pharmaceutical skeletons. Preliminary mechanistic studies suggest a lower energy barrier for aliphatic C = O insertion, explaining the high regioselectivity observed in this reduction.
Article
Chemistry, Organic
Jinghui Hu, Qiang Du, Yao Zhao, Fei Zhang, Rizhi Chen, Jianrong Steve Zhou, Xiaojin Wu
Summary: A nickel-catalyzed intermolecular arylcyanation reaction of 8-aminoquinolinyl beta,gamma-unsaturated amides is reported. Diverse beta-cyano gamma-aryl amides with exclusive chemo- and regioselectivity were directly obtained through a three-component reaction. The practicality of this approach was further demonstrated through multigram scale reactions, expanded transformations of the nitrile product, late-stage modification of complex molecules, and direct drug synthesis.
Article
Chemistry, Organic
Xue-Lin Dai, Jingdi Ran, Thayalan Rajeshkumar, Zhengping Xu, Shanshan Liu, Zongchao Lv, Laurent Maron, Yi-Hung Chen
Summary: The metal-mediated propargylation or allenylation of carbonyl compounds is useful for the synthesis of homopropargylic or allenylic alcohols, which are important intermediates in synthetic chemistry. However, controlling the regioselectivity of these reactions is challenging due to the equilibrium between propargyl and allenyl metal reagents. In this study, propargyl or allenyl organolanthanum reagents were prepared and react with aldehydes to yield the desired regioselective products. This research provides insights into the structural specificity and chemoselectivity of rare earth metal reagents.
Article
Chemistry, Multidisciplinary
Cole C. Meyer, Zachary J. Dubey, Michael J. Krische
Summary: This study systematically investigates the enantioselective additions to symmetric ketones for the first time. By generating the cyclometallated iridium-PhanePhos complexes in situ, the 2-propanol-mediated reductive couplings were catalyzed, resulting in the formation of branched homoallylic oxetanols and azetidinols.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Chengyu Yu, Guoren Yue, Penji Yan, Hai Song, Hucheng Shi, Yangfei Wei, Zhengen Song, Xin Jia
Summary: A novel synthesis of highly functionalized dihydrofuranyl alcohols has been developed through a tandem process, resulting in good yields of up to 97.1%.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Yaomei Liu, Zuming Wu, Wenjing Li, Mengjiao Zhang, Youhui Zhang, Shuqin Deng, Shilu Fan, Yanwu Zhu, Yi-Si Feng
Summary: Herein, we report a dicarbonylation reaction of styrenes with aryl fluorides and potassium 2-ethoxy-2-oxoacetate using cooperative NHC and photoredox catalysis. This method exhibits good functional group tolerance and provides moderate to high yields, offering a valuable alternative approach for the synthesis of beta-arylketoesters. Mechanistic studies reveal that the reaction proceeds through a radical-addition/coupling/elimination cascade.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Yao Huang, Suchen Zou, Bangkui Yu, Xuyang Yan, Song Liu, Hanmin Huang
Summary: A ligand-controlled palladium-catalyzed reaction has been developed for the regioselective and diastereodivergent aminomethylative annulation of dienyl alcohols with aminals. This reaction allows for the production of cis- or trans-disubstituted isochromans with excellent regioselectivity and diastereoselectivity. Chiral cis-products can also be obtained with high enantioselectivity using a chiral phosphinamide ligand. Mechanistic studies revealed the key role of the hydroxyl group in the regioselective insertion across the internal C=C bond of conjugated dienes.
Article
Chemistry, Multidisciplinary
Colton R. Davis, Irungu K. Luvaga, Joseph M. Ready
Summary: Alkenyl boronates react with Ir(pi-allyl) intermediates to form products with high enantioselectivity, establishing multiple C-C bonds. The reaction provides tertiary boronic esters that can undergo multiple functionalizations. Extension to trisubstituted olefins results in the formation of three contiguous stereocenters.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Gillian Laidlaw, Vilius Franckevicius
Summary: A palladium-catalyzed decarboxylative asymmetric allylic alkylation has been developed for the synthesis of specific compounds, demonstrating potential for medicinal chemistry applications.
Article
Chemistry, Multidisciplinary
Dong-Sheng Ji, Hui Liang, Kai-Xuan Yang, Zhi-Tao Feng, Yong-Chun Luo, Guo-Qiang Xu, Yucheng Gu, Peng-Fei Xu
Summary: A chemically divergent synthesis of beta-lactams and alpha-amino acid derivatives was achieved by using isothiourea (ITU) catalysis and switching solvents, demonstrating the versatility of this method.
Article
Chemistry, Multidisciplinary
Kun Liu, Armido Studer
Summary: N-Heterocyclic carbene (NHC) catalysis is a versatile tool in modern synthetic chemistry, often used in concert with a second catalytic moiety to expand reaction scope. Triple catalysis, merging three different catalytic modes in a single process, has been recently studied, allowing for the synthesis of complex compounds. In a reported study, alpha-C-H acylation of alkenes using NHC, sulfinate, and photoredox cooperative triple catalysis was achieved, highlighting the potential of such synergistic catalytic systems.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Radha Bam, Wesley A. Chalifoux
JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Wenlong Yang, Rezvan R. Kazemi, Nelum Karunathilake, Vincent J. Catalano, Mario A. Alpuche-Aviles, Wesley A. Chalifoux
ORGANIC CHEMISTRY FRONTIERS
(2018)
Article
Chemistry, Multidisciplinary
Wenlong Yang, Radha Bam, Vincent J. Catalano, Wesley A. Chalifoux
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Multidisciplinary
Wenlong Yang, Jorge H. S. K. Monteiro, Ana de Bettencourt-Dias, Vincent J. Catalano, Wesley A. Chalifoux
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Chemistry, Organic
Khagendra B. Hamal, Paban Sitaula, Wesley A. Chalifoux
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Review
Biochemistry & Molecular Biology
Amber D. Senese, Wesley A. Chalifoux
Article
Chemistry, Organic
Clement De Hoe, Ryan T. Dean, Allison S. Hacker, Sudeep H. Dutta, Omar Dominguez, Leo W. T. Parsons, Parker J. W. Sommerville, Kai P. Vandivier, Wesley A. Chalifoux, Derik K. Frantz
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Radha Bam, Wenlong Yang, Giovanna Longhi, Sergio Abbate, Andrea Lucotti, Matteo Tommasini, Roberta Franzini, Claudio Villani, Vincent J. Catalano, Marilyn M. Olmstead, Wesley A. Chalifoux
Article
Chemistry, Organic
Wesley A. Chalifoux, Paban Sitaula, Ryan J. Malone, Giovanna Longhi, Sergio Abbate, Eva Gualtieri, Andrea Lucotti, Matteo Tommasini, Roberta Franzini, Claudio Villani, Vincent J. Catalano
Summary: A mild and efficient synthesis method has been developed for the synthesis of a broad range of substituted naphtho[1,2-a]pyrene derivatives. The reaction exhibited good yields and used InCl3/AgNIf(2) as the catalyst for the two-fold alkyne benzannulation reaction. HPLC enantiomeric separation and determination of interconversion barriers were achieved. The ECD and Raman spectra of the derivatives were recorded and interpreted through TD-DFT and DFT calculations, respectively.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Zachary W. Schroeder, Robert McDonald, Michael J. Ferguson, Wesley A. Chalifoux, Rik R. Tykwinski, Dan Lehnherr
Summary: A general method for the synthesis of ethynylated pentacene ketones is reported, and key noncovalent interactions contributing to their crystallization are revealed by X-ray crystallography.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Electrochemistry
Shakirul M. Islam, Ryan J. Malone, Wenlong Yang, Stephen P. George, Rajendra P. Gautam, Wesley A. Chalifoux, Christopher J. Barile
Summary: In this study, we designed a new type of Zn-ion battery by combining molecularly-precise nanographene cathodes with metallic Zn anodes. The results showed that twisted peropyrene electrodes enabled reversible Zn-ion intercalation in a nonaqueous electrolyte, which expands the design space of nonaqueous multivalent batteries. This finding is important for the development of high-voltage nonaqueous battery systems.
JOURNAL OF THE ELECTROCHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Ryan J. Malone, Jonas Spengler, Rachael A. Carmichael, Khoa Ngo, Frank Wuerthner, Wesley A. Chalifoux
Summary: Achiral and chiral isomers of dipyrenoheteroles were synthesized through alkyne benzannulation. The electronic properties of these compounds were analyzed using cyclic voltammetry and differential pulse voltammetry. The enantiomers of the chiral isomers were separated and their optical properties were examined using circular dichroism and circularly polarized luminescence studies. The chiral isomers showed a significant bathochromic shift in both absorbance and fluorescence, resulting from decreased symmetry rather than a change in the backbone size.
Review
Chemistry, Organic
Hannah V. V. Anderson, Nicolai D. D. Gois, Wesley A. A. Chalifoux
Summary: Chiral nanographenes, which combine the properties of inherently chiral molecules with the optical, electronic, and magnetic properties of nanographenes, show potential for new applications in nanoelectronics. Recent advances in synthetic design have allowed for the fine-tuning of these properties, leading to the preparation of novel chiral nanographenes. This article highlights recent, noteworthy, and less-reviewed contributions in the preparation of chiral nanographenes.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Review
Chemistry, Organic
Kelsie M. Magiera, Vivek Aryal, Wesley A. Chalifoux
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Wenlong Yang, Jorge H. S. K. Monteiro, Ana de Bettencourt-Dias, Wesley A. Chalifoux
CANADIAN JOURNAL OF CHEMISTRY
(2017)