Article
Chemistry, Multidisciplinary
F. Wieland Goetzke, Alexander M. L. Hell, Lucy van Dijk, Stephen P. Fletcher
Summary: The study describes an asymmetric cross-coupling reaction between cyclobutenes and arylboronic acids initiated by Rh-catalyzed asymmetric carbometallation. This method allows for the synthesis of highly stereoselective cyclobutane derivatives and demonstrates wide applicability in drug synthesis.
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
Christopher A. Wilhelmsen, Xuntong Zhang, Jesse A. Myhill, James P. Morken
Summary: Versatile beta tert-boryl amides were synthesized through conjunctive cross-coupling of alpha-substituted alkenyl boron ate complexes and carbamoyl chloride electrophiles. The use of a palladium catalyst in combination with MandyPhos enabled enantioselective synthesis. Additionally, the chemoselectivity of the reaction product was enhanced by the addition of water.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Zhenyu Li, Xuan Ai, Hui Chen, Xiao Liang, Xiaotian Li, Dong Wang, Xiaoxin Zou
Summary: Intermetallic rhodium boride (RhB) is synthesized with an asymmetrically strained hcp Rh sublattice, in which the covalent interaction of interstitial boron atoms is identified as the main contributor. Additionally, RhB is recognized as a hydrogen-evolving electrocatalyst with Pt-like activity, attributed to the optimized electronic structure induced by Rh(d)-B(s,p) orbital hybridization.
CHEMICAL COMMUNICATIONS
(2021)
Review
Chemistry, Applied
Puthukudichola Krishna Soumya, Thottuvazhiyil Balakrishnan Vaishak, Salim Saranya, Gopinathan Anilkumar
Summary: Cyanation reactions play a dominant role in organic synthesis due to the easy conversion of cyanide groups to various other functionalities. Transition metal-catalyzed reactions, particularly rhodium-catalyzed reactions, have attracted attention from organic chemists, leading to the synthesis of highly functionalized products through various cyanation procedures.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jeremy Brals, Thomas M. McGuire, Allan J. B. Watson
Summary: We report the development of a novel coupling reaction using styrene boronic acids and redox-active esters under photoredox catalysis. The reaction proceeds through an unusual polarity-mismatched radical addition mechanism, enabling chemoselective coupling of styrene boronic acids in the presence of other alkene radical acceptors.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Muriel Durandetti
Summary: The direct formation of C-C bonds catalyzed by nickel complexes has become an important research topic in the past fifty years, and has recently seen a resurgence as a new area in nickel chemistry. This paper provides a summary of the use of nickel complexes in catalysis and highlights the evolution of the authors' own research.
Article
Chemistry, Physical
Bing Zhang, Xin Xu, Lei Tao, Zhenyang Lin, Wanxiang Zhao
Summary: In this study, an efficient rhodium-catalyzed deoxygenative borylation of ketones was reported to synthesize alkylboronates, with regioselectivity controlled by the choice of ligand. Different steric effects of ligands were found to be responsible for product selectivity. The reaction pathway involves an alkene intermediate which undergoes regiodivergent hydroboration to afford linear and branched alkylboronates, or sequential dehydrogenative borylation and hydroboration to deliver triboronates.
Article
Chemistry, Organic
Sophia G. Gierszal, Timothy J. Barker
Summary: The reaction between epoxides and benzylboronic acid pinacol esters was efficiently catalyzed by CuI upon activation of the benzylboronic ester with an alkyllithium reagent. The reaction showed good regioselectivity with a variety of substituted epoxides, but a reaction using an enantioenriched secondary benzylboronic ester was found to not be stereospecific.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Nicola L. Bell, Chao Xu, James W. B. Fyfe, Julien C. Vantourout, Jeremy Brals, Sonia Chabbra, Bela E. Bode, David B. Cordes, Alexandra M. Z. Slawin, Thomas M. McGuire, Allan J. B. Watson
Summary: A novel Cu-mediated C-N cross-coupling reaction has been identified in this study, which can be applied to drug synthesis and late-stage N-arylation. Mechanistic studies have provided evidence for the limitations in the methodology.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Akanksha Singh Baghel, Anjali Aghi, Amit Kumar
Summary: The regioselective ortho-alkenylation of primary benzamides with activated olefins using a Ru(II) catalyst has been achieved, allowing the controlled introduction of olefin motifs at the ortho-position of benzamides. The success of this strategy relies on fine-tuning reaction conditions and involves a base-assisted internal electrophilic-type substitution step in the reaction mechanism.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
L. Reginald Mills, Racquel K. Edjoc, Sophie A. L. Rousseaux
Summary: New ligands are designed to exploit the reactivity of nitrile-containing additives in Ni catalysis for cross-coupling reactions involving tertiary nucleophiles. Kinetic and Hammett studies elucidate the role of the optimized ligand, promoting reductive elimination and stabilizing low-valent Ni. This study enables the synthesis of quaternary alpha-arylnitriles from disubstituted malononitriles through decyanation-metalation and Ni-catalyzed arylation.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Mahmoud K. Al-Joumhawy, Tarek Marei, Akim Shmalko, Paula Cendoya, Jair La Borde, Detlef Gabel
Summary: The study demonstrates a microwave-assisted palladium-catalyzed amination method for iodododecaborate with aromatic amines, HN-containing heteroaromatics, and amides, allowing for efficient synthesis of amides, dodecaborate-substituted anilines, and the first-time substitution of dodecaborate with HN-containing heterocycles.
CHEMICAL COMMUNICATIONS
(2021)
Review
Chemistry, Multidisciplinary
Stavros K. Kariofillis, Abigail G. Doyle
Summary: In recent years, the development of light-driven reactions has made significant advancements in synthetic organic chemistry, particularly in combining photoredox and nickel catalysis for challenging cross-coupling reactions. The question of whether photo-induced activation of the nickel catalyst itself could lead to new approaches to cross-coupling has been explored. By utilizing a visible-light-driven mechanism for chlorine radical formation and conducting mechanistic investigations on organometallic Ni complexes relevant to cross-coupling, the study aims to facilitate new catalyst design and develop novel synthetic methods.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Article
Chemistry, Organic
Shimeng Li, Jie Zhang, Zuowei Xie
Summary: This work describes a general method for the efficient production of a class of cage B-centered carboranyl radicals, which are useful intermediates for the preparation of a family of cage B-(hetero)arylated o-carboranes.
Article
Chemistry, Organic
Devin M. Ferguson, Christian A. Malapit, James R. Bour, Melanie S. Sanford
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
Christian A. Malapit, James R. Bour, Simon R. Laursen, Melanie S. Sanford
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2019)
Article
Chemistry, Multidisciplinary
Mengwei Yuan, Sofiene Abdellaoui, Hui Chen, Matthew J. Kummer, Christian A. Malapit, Chun You, Shelley D. Minteer
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Christian A. Malapit, Margarida Borrell, Michael W. Milbauer, Conor E. Brigham, Melanie S. Sanford
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Multidisciplinary
Fangyuan Dong, Hui Chen, Christian A. Malapit, Matthew B. Prater, Min Li, Mengwei Yuan, Koun Lim, Shelley D. Minteer
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Physical
Conor E. Brigham, Christian A. Malapit, Naish Lalloo, Melanie S. Sanford
Article
Chemistry, Multidisciplinary
Pengfei Hu, Byron K. Peters, Christian A. Malapit, Julien C. Vantourout, Pan Wang, Jinjun Li, Lucas Mele, Pierre-Georges Echeverria, Shelley D. Minteer, Phil S. Baran
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Multidisciplinary
Masato Saito, Yu Kawamata, Michael Meanwell, Rafael Navratil, Debora Chiodi, Ethan Carlson, Pengfei Hu, Longrui Chen, Sagar Udyavara, Cian Kingston, Mayank Tanwar, Sameer Tyagi, Bruce P. McKillican, Moses G. Gichinga, Michael A. Schmidt, Martin D. Eastgate, Massimiliano Lamberto, Chi He, Tianhua Tang, Christian A. Malapit, Matthew S. Sigman, Shelley D. Minteer, Matthew Neurock, Phil S. Baran
Summary: This translation discusses the importance of site-specific C-H bond oxidation in organic synthesis and the current limitations of chemical reagents in achieving this transformation. It introduces a platform using N-ammonium ylides as oxidants for site-specific, chemoselective C-H oxidation, which is guided by computation and can be applied to real-world problems in the agricultural and pharmaceutical sectors.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Review
Chemistry, Multidisciplinary
Christian A. Malapit, Matthew B. Prater, Jaime R. Cabrera-Pardo, Min Li, Tammy D. Pham, Timothy Patrick McFadden, Skylar Blank, Shelley D. Minteer
Summary: Synthetic organic electrosynthesis has made significant progress in recent decades, improving both selectivity and efficiency, and exploring new transformations and sustainable reactions. This review discusses the latest advances in combining electrochemistry and homogeneous transition-metal catalysis for organic synthesis, and explores future directions and challenges in the field.
Article
Chemistry, Multidisciplinary
Naish Lalloo, Christian A. Malapit, S. Maryamdokht Taimoory, Conor E. Brigham, Melanie S. Sanford
Summary: This article describes the development of a decarbonylative Pd-catalyzed aryl-fluoroalkyl bond-forming reaction. By optimizing the individual steps of the catalytic cycle to identify compatible coupling partners and an appropriate Pd catalyst, an efficient method for decarbonylative difluoromethylation of aryl neopentylglycol boronate esters with difluoroacetyl fluoride was achieved.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Hui Chen, Tianhua Tang, Christian A. Malapit, Yoo Seok Lee, Matthew B. Prater, N. Samali Weliwatte, Shelley D. Minteer
Summary: Petroleum hydrocarbons are a major energy source and an important feedstock for the chemical industry. The deep conversion of inert hydrocarbons to more valuable chemicals is a significant challenge. In this study, a multistep bioelectrocatalytic system was developed to achieve the one-pot deep conversion of heptane to N-heptylhepan-1-imine. This system successfully realized the conversion of inert hydrocarbons to imines, providing a new methodology for the comprehensive conversion and utilization of inert hydrocarbons.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Multidisciplinary Sciences
Samer Gnaim, Adriano Bauer, Hai-Jun Zhang, Longrui Chen, Cara Gannett, Christian A. Malapit, David E. Hill, David Vogt, Tianhua Tang, Ryan A. Daley, Wei Hao, Rui Zeng, Mathilde Quertenmont, Wesley D. Beck, Elya Kandahari, Julien C. Vantourout, Pierre-Georges Echeverria, Hector D. Abruna, Donna G. Blackmond, Shelley D. Minteer, Sarah E. Reisman, Matthew S. Sigman, Phil S. Baran
Summary: The study and application of TMHs in energy storage and organic synthesis is of great importance. The electrochemical approach for utilizing TMHs in organic synthesis offers benefits in terms of sustainability, efficiency, chemoselectivity, and reactivity.
Review
Chemistry, Physical
Stella A. Fors, Christian A. Malapit
Summary: In the past few decades, most of the progress in CO2 reduction has been focused on the synthesis of C1 products, such as CO, formic acid, methanol, and methane. However, the syntheses of C2+ products from generally abundant C1 sources such as CO2, CO, and CH4 have traditionally been more challenging. Recent advances in organometallic chemistry and catalysis have provided effective methods for converting C1 sources to higher-energy C2+ products under mild conditions. Moreover, these advancements have enabled the use of various C1 sources for the generation of different C2+ products through C-C bond formation. This review systematically presents the recent advances in C1 to C2+ conversions under homogeneous catalysis.
Meeting Abstract
Chemistry, Multidisciplinary
Conor Brigham, Christian Malapit, Melanie Sanford
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2019)
Meeting Abstract
Chemistry, Multidisciplinary
Conor Brigham, Christian Malapit, Melanie Sanford
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2019)
