Article
Chemistry, Inorganic & Nuclear
Rajata Kumar Sahoo, Sagrika Rajput, A. Ganesh Patro, Sharanappa Nembenna
Summary: A structurally characterized conjugated bis-guanidinate supported zinc(I) dimer with a Zn-Zn bond is reported, and its catalytic activity in the dehydroborylation of various terminal alkynes is studied. A plausible reaction mechanism is proposed through stoichiometric experiments.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Inorganic & Nuclear
Subir Maji, Pallavi Sarkar, Arpan Das, Swapan K. Pati, Swadhin K. Mandal
Summary: In this study, a novel benzimidazo-lylidene-stabilized borane adduct and its borenium ion were synthesized and used as a metal-free catalyst for hydrogenation reactions. Various substituted quinoline N-heterocycles were successfully hydrogenated under ambient conditions, and two drug molecules were synthesized using this method. The mechanism of catalytic hydrogenation was investigated through detailed DFT studies.
INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Sourabh Mishra, Florian C. T. Modicom, Conor L. Dean, Stephen P. Fletcher
Summary: The authors report a method to produce carbocyclic C-nucleosides (CC-Ns) using an asymmetric Suzuki-Miyaura coupling reaction as the key C-C bond forming step. This approach allows the production of a variety of enantiomerically enriched CC-Ns, including the antiviral showdomycin.
COMMUNICATIONS CHEMISTRY
(2022)
Review
Chemistry, Physical
Aishwarya Prakash, Suresh Saini, Suma Basappa, Dharmendra Kumar Gupta, Lujia Mao, Shubhankar Kumar Bose
Summary: Organoboranes are important reagents in synthetic organic chemistry, and their C-B bonds can be transformed into C-X (X=C, N, O, and halogen) bonds stereoretentively to provide valuable complex molecules. Homogeneous transition-metal-catalyzed borylation reactions are effective methods for synthesizing organoboranes, but the inability to recover catalysts and metal contamination in products limits their application. Metal-organic frameworks (MOFs)-based heterogeneous catalytic systems have gained prominence in overcoming these limitations.
Article
Chemistry, Multidisciplinary
Antonio Pulcinella, Daniele Mazzarella, Timothy Noel
Summary: The conversion of light alkanes into bulk chemicals faces challenges due to their gaseous nature and low solubility, but efforts to activate inert compounds and develop suitable reactor technology have shown promise. Recent developments have enabled the use of different gaseous alkanes for various bond-forming reactions.
CHEMICAL COMMUNICATIONS
(2021)
Review
Chemistry, Physical
Xinyue Tan, Huadong Wang
Summary: This review summarizes the recent progress in the catalytic C-H borylation of (hetero)arenes, with a focus on synthetic application and reaction mechanisms.
Article
Chemistry, Multidisciplinary
Wenbo Ming, Yashi Xu, Libo Xiang, Qing Ye
Summary: In this study, a bottleable super electron donor catalyst, [(Dpp-bian)B(DMAP)](2) , is used for the borylation of aryl iodides, bromides, and challenging chlorides. The protocol is not only capable of installing Bpin from B(2)pin(2) but also allows for installing Bdan from Bpin-Bdan. The radical mechanism is confirmed through radical trapping and radical clock experiments.
CHEMICAL COMMUNICATIONS
(2023)
Article
Multidisciplinary Sciences
Hayden A. Sharma, Jake Z. Essman, Eric N. Jacobsen
Summary: This study presents a strategy for constructing a wide variety of trisubstituted stereocenters through enantioselective, catalytic 1,2-boronate rearrangements. The chiral building blocks produced in these reactions can undergo two sequential stereospecific elaborations to generate a wide assortment of trisubstituted stereocenters. The enantioselective reaction is catalyzed by a lithium-isothiourea-boronate complex, which promotes rearrangement through a dual-lithium-induced chloride abstraction orchestrated by Lewis basic functionality on the catalyst scaffold.
Article
Chemistry, Multidisciplinary
Hao Zheng, Chang-Hui Liu, Xiao-Yu Wang, Yan Liu, Bing-Zhi Chen, Yan-Cheng Hu, Qing-An Chen
Summary: This article reports an efficient iridium-catalyzed meta-selective C-H borylation reaction that allows for the rapid synthesis of various boronic esters based on benzoferrocenes, ferrocenes, ruthenocene, and related half sandwich complexes. This method does not require preinstalled directing groups and is compatible with a wide range of electron-deficient and -rich functional groups. The scalability and diverse applications of this reaction, including the conversion of boron to heteroatoms and cross-coupling reactions, are also demonstrated.
Article
Chemistry, Multidisciplinary
Yanhua Lu, Yafei Li, Yeye She, Chaohong Jia, Yahong Li
Summary: This article describes the syntheses, characterizations, and catalytic activities of three zinc complexes and one lithium compound based on beta-diketiminate ligands. The reaction of ZnEt2 with HL1 ligand produced compounds [(L-1)ZnEt] (1) and [(L-1)(2)Zn] (2). Deprotonation of H2L2 ligand by (BuLi)-Bu-n generated complex [(L-2)Li-2(THF)(2)] (3). Compound 3 reacted with anhydrous zinc chloride to produce [(HL2)Zn2Cl3].Tol (4 Tol). Compounds 1 and 4 showed activity for borylation reactions, with compound 4 displaying higher activity. Compound 3 was not active for borylation but showed excellent catalytic performance in the hydroboration of aldehydes and ketones.
NEW JOURNAL OF CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Allison M. Arinaga, Morgan C. Ziegelski, Tobin J. Marks
Summary: Research on the catalytic oxidative coupling of methane (OCM) using alternative oxidants such as N2O, CO2, and S-2 is still in its early stages, with unique advantages and challenges compared to oxygen (O-2) as the oxidant. This area has not been extensively reviewed, despite the renewed interest in OCM due to the abundance of shale gas resources.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Multidisciplinary Sciences
Qiaomu Yang, Yu-Heng Wang, Yusen Qiao, Michael Gau, Patrick J. Carroll, Patrick J. Walsh, Eric J. Schelter
Summary: The reported carbon-hydrogen (C-H) activation of alkanes is actually mediated by the photocatalyst [NEt4](2)[CeCl6], and RO center dot are not intermediates. The generation of chlorine radical (Cl center dot) in the photocatalytic system is found to be the rate-limiting step. Density functional theory calculations support the formation of [Cl center dot][alcohol] adducts, which can manifest a masked RO center dot character.
Article
Chemistry, Physical
Koji Kubota, Daiyo Miura, Takumi Takeuchi, Shun Osaki, Hajime Ito
Summary: The study introduces a novel catalytic enantioselective nucleophilic borylation reaction of ketimines, leading to the efficient synthesis of optically active alpha-amino tertiary boronates with high enantioselectivity. The products can be further converted into peptidylboronic acid derivatives that are difficult to synthesize by other methods. Density functional theory calculations suggest that noncovalent interactions play a crucial role in determining the enantioselectivity of this reaction.
Editorial Material
Chemistry, Multidisciplinary
Christine M. DuChane, Jiawei Chen
Summary: The study presents a novel approach utilizing an NHC-stabilized hydroborenium cation for selective C-H activation of methane without transition metals, leading to valuable borylated products.
Review
Chemistry, Multidisciplinary
Maria Batuecas, Nikolaus Gorgas, Mark R. Crimmin
Summary: This passage discusses the importance of C-H functionalization, particularly the fast-developing field of C-H borylation. It focuses on palladium- and calcium-catalyzed methods for C-H metalation, revealing new reaction pathways and mechanisms.
Article
Chemistry, Multidisciplinary
Jose R. Montero Bastidas, Thomas J. Oleskey, Susanne L. Miller, Milton R. Smith, Robert E. Maleczka
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2019)
Article
Chemistry, Multidisciplinary
Jisun Lee, Jason R. Schmink, Simon Berritt
JOURNAL OF CHEMICAL EDUCATION
(2020)
Review
Chemistry, Multidisciplinary
Geletu Qing, Reza Ghazfar, Shane T. Jackowski, Faezeh Habibzadeh, Mona Maleka Ashtiani, Chuan-Pin Chen, Milton R. Smith, Thomas W. Hamann
Article
Biochemistry & Molecular Biology
Ghayoor A. Chotana, Jose R. Montero Bastidas, Susanne L. Miller, Milton R. Smith, Robert E. Maleczka
Article
Biochemistry & Molecular Biology
R. Chauncey Splichal, Joseph A. Gredell, Erin B. Vogel, Amanda Malefyt, Georgina Comiskey, Milton R. Smith, Christina Chan, S. Patrick Walton
Summary: The study synthesized a variety of cationic poly(propargyl glycolide) backbone polymers using click chemistry to bind and deliver siRNAs, demonstrating control over binding interactions and effective delivery with no cytotoxicity. Despite comparable accumulation levels with commercial reagents, there was no observed silencing effect on the targeted protein.
NUCLEIC ACID THERAPEUTICS
(2021)
Article
Microscopy
Daniel Vocelle, Olivia M. Chesniak, Milton R. Smith, Christina Chan, S. Patrick Walton
Article
Biochemistry & Molecular Biology
Hosung Ki, Sungjun Park, Seunghwan Eom, Jain Gu, Siim Kim, Changwon Kim, Chi Woo Ahn, Minseo Choi, Sena Ahn, Doo-Sik Ahn, Jungkweon Choi, Mu-Hyun Baik, Hyotcherl Ihee
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2020)
Article
Chemistry, Organic
Bowen Li, Bangke Luo, Caroline A. Blakemore, Aaron C. Smith, Daniel W. Widlicka, Simon Berritt, Wenjun Tang
Summary: A practical and efficient synthesis of alpha-heteroaryl propionic esters was achieved by employing palladium-catalyzed alpha-heteroarylation of silyl ketene acetals, forming a wide variety of esters with different substituents and functionalities in high yields. The success of this transformation can be attributed to the development of a bulky P,P=O ligand, providing an efficient synthesis of alpha-heteroaryl propionic acids.
Article
Chemistry, Organic
Chathurika R. K. Jayasundara, Jose M. Gil-Negrete, Jose R. Montero Bastidas, Arzoo Chhabra, M. Montserrat Martinez, Jose Perez Sestelo, Milton R. Smith, Robert E. Maleczka
Summary: A versatile and efficient method for the synthesis of borylated arenes with various functional groups has been developed by combining Ir-catalyzed C-H borylations with a palladium-catalyzed cross-coupling reaction. This method allows for the introduction of unsaturated moieties using triorganoindium reagents, enabling the synthesis of borylated arenes that are difficult to access through traditional methods. The sequential double catalyzed procedure can be conducted in a single vessel, making it a convenient and practical approach for the preparation of diverse borylated arenes.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Multidisciplinary Sciences
Dafydd R. Owen, Charlotte M. N. Allerton, Annaliesa S. Anderson, Lisa Aschenbrenner, Melissa Avery, Simon Berritt, Britton Boras, Rhonda D. Cardin, Anthony Carlo, Karen J. Coffman, Alyssa Dantonio, Li Di, Heather Eng, RoseAnn Ferre, Ketan S. Gajiwala, Scott A. Gibson, Samantha E. Greasley, Brett L. Hurst, Eugene P. Kadar, Amit S. Kalgutkar, Jack C. Lee, Jisun Lee, Wei Liu, Stephen W. Mason, Stephen Noell, Jonathan J. Novak, R. Scott Obach, Kevin Ogilvie, Nandini C. Patel, Martin Pettersson, Devendra K. Rai, Matthew R. Reese, Matthew F. Sammons, Jean G. Sathish, Ravi Shankar P. Singh, Claire M. Steppan, Al E. Stewart, Jamison B. Tuttle, Lawrence Updyke, Patrick R. Verhoest, Liuqing Wei, Qingyi Yang, Yuao Zhu
Summary: PF-07321332, an orally bioavailable SARS-CoV-2 main protease inhibitor, has been discovered with in vitro pan-human coronavirus antiviral activity and excellent off-target selectivity and in vivo safety profiles. This new drug has shown promise in countering the threat of COVID-19 with its oral activity and safety in clinical trials.
Article
Chemistry, Organic
Jonathan E. Dannatt, Anshu Yadav, Milton R. Smith, Robert E. Maleczka
Summary: A bidentate monoanionic ligand system was developed for iridium catalyzed C(sp(3))-H activation borylation of N-methyl amides. The borylated amides were obtained with moderate to good isolated yields, and exclusive mono-borylation allowed the amide to be the limiting reagent. The selectivity for C(sp(3))-H activation was demonstrated even in the presence of sterically available C(sp(3))-H bonds. Competitive kinetic isotope studies revealed a large primary isotope effect, indicating that C-H activation is the rate-limiting step.
Article
Chemistry, Physical
Jose R. Montero Bastidas, Arzoo Chhabra, Yilong Feng, Thomas J. Oleskey, Milton R. Smith, Robert E. Maleczka
Summary: This study reveals that intramolecular hydrogen bonding can play a key role in directing regioselectivity in Ir-catalyzed C-H borylation reactions, leading to steric shielding effects that promote remote borylations of specific substrates.
Article
Chemistry, Physical
Chenjia Mi, Reza Ghazfar, Milton R. Smith, Thomas W. Hamann
Summary: This study reports the transformation of gaseous ammonia to a liquid at room temperature and ambient pressure by mixing with solid ammonium salts. The resulting liquid, called eurefstics, is advantageous for ammonia storage, electrochemical conversion, and green ammonia energy economy. The physical and electrochemical properties of the eurefstics are investigated, and their potential applications in ammonia electrolysis are explored. Safety concerns are also discussed in comparison with other liquid phase energy carriers.
Article
Chemistry, Organic
Allyn T. Londregan, John M. Curto, Emma Hastry, Colin R. Rose, Simon Berritt
Summary: In this study, a general and convenient procedure for the synthesis of azinones is presented. Cyclopropylmethanol is used as a protecting group and surrogate for hydroxyl in various azines. The corresponding azinones can be formed and isolated in excellent yields after acidic deprotection under mild reaction conditions. More than 20 examples, along with reaction optimization, scope, and mechanism, are discussed.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Medicinal
Emma L. McInturff, Scott P. France, Carolyn A. Leverett, Andrew C. Flick, Erick A. Lindsey, Simon Berritt, Daniel W. Carney, Jacob C. DeForest, Hong X. Ding, Sarah J. Fink, Tony S. Gibson, Kaitlyn Gray, Aran K. Hubbell, Amber M. Johnson, Yiyang Liu, Subham Mahapatra, Indrawan J. McAlpine, Rebecca B. Watson, Christopher J. O'Donnell
Summary: New drugs introduced to the market each year provide valuable insights into molecular recognition and potential leads for future medicines. This annual review focuses on the process-scale synthetic approaches to 35 newly approved compounds worldwide in 2021, including small molecules and antibody-drug conjugates.
JOURNAL OF MEDICINAL CHEMISTRY
(2023)
