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Julia A. Kalow
JULIA A. KALOW Department of Chemistry Northwestern University Technological Institute, M290 (847) 467-4972 2145 Sheridan Rd [email protected] Evanston, IL 60208 http://sites.northwestern.edu/kalowlab/ RESEARCH EXPERIENCE Assistant Professor, Northwestern University, Department of Chemistry 2016–present Ruth L. Kirschstein Postdoctoral Fellow, Massachusetts Institute of Technology 2013–2016 Advisor: Professor Timothy M. Swager • Developed an efficient synthesis of telechelic P3HT and a versatile strategy to prepare miktoarm branched polymers based on ring-opening metathesis polymerization. • Studied the self-assembly of novel architectures of conjugated polymers in solution and in bulk. • Collaborated with a team of researchers studying tunable complex emulsions and applied these emulsions to enzyme sensing. • Mentored a visiting undergraduate student from Tianjin University (Xinping He). Graduate Research Assistant, Princeton University, Department of Chemistry 2008–2013 Advisor: Professor Abigail G. Doyle Thesis title: Catalytic strategies for asymmetric nucleophilic fluorination using a latent HF source: Development and mechanistic investigations • Initiated a program in asymmetric catalytic nucleophilic fluorination in the Doyle lab and introduced the use of benzoyl fluoride as a latent HF source for C–F bond formation. • Discovered key mechanistic insights into cooperative catalysis in the fluorination reactions that have led to additional projects, including selective radiofluorination. • Mentored an undergraduate chemistry major (Dana Schmitt, class of 2012). Intern, Merck Research Laboratories, Medicinal Chemistry, Boston, MA Summer 2007 • Investigated metal-catalyzed trifluoromethylation methods (with Dr. Jed Hubbs). Undergraduate Researcher, Columbia University, Department of Chemistry 2005–2008 Advisor: Professor James L. Leighton • Participated in studies toward the synthesis of isocyclocitrinol A (with Dr. Arash Soheili). • Developed an enantioselective imino-Nazarov rearrangement (with Dr. -
SCS Annual Report 2019
SCS Swiss Chemical Society Annual Report 2019 SCS Award Winners 2019 Published in CHIMIA Volume 74, No 1-2/2020 scg.ch/awards David Spichiger Introduction and Strategy The SCS awarded six individuals and one group of scientists for their outstanding contributions. A total sum of CHF 80’000 as well as medals and award certificates were given to the prize winners. With pleasure we look back on a very interesting and active year. The Swiss Chemical Society not only continued and developed its Werner Prize well-established activities but again pushed new initiatives to face CHF 10'000 and medal in bronze; awarded to a promising young todays challenges. We also implemented new sections and net- scientist for outstanding independent chemical research. The works to incorporate community members whose interest were award was given to not covered so far. In addition, the SCS took over the responsibil- ity for existing programs that run now under the umbrella of the Prof. Jeremy Luterbacher, SCS and complete its activity portfolio. EPFL Lausanne, The most important, new initiatives in 2019: for his original and groundbreaking § SCS took over the operative responsibility for the Swiss National research on chemical conversion of plant Technology Platform of SusChem to push the Green & Sustain- material using protection group chemistry able Chemistry approach in the chemical R&D; during biomass depolymerization and § Within the Division of Analytical Sciences, the Section of Chem- upgrading. istry and the Environmental was founded and initiated initiatives The prize was given on the occasion of that will be implemented in 2020; the SCS Spring Meeting in Dübendorf on April 5, 2019. -
Aldrichimica Acta 50.1, 2017
VOLUME 50, NO. 1 | 2017 ALDRICHIMICA ACTA 4-Substituted Prolines: Useful Reagents in Enantioselective HIMICA IC R A Synthesis and Conformational Restraints in the Design of D C L T Bioactive Peptidomimetics A A Recent Advances in Alkene Metathesis for Natural Product Synthesis—Striking Achievements Resulting from Increased 1 7 9 1 Sophistication in Catalyst Design and Synthesis Strategy 68 20 The life science business of Merck KGaA, Darmstadt, Germany operates as MilliporeSigma in the U.S. and Canada. From the Editor's Desk The Aldrichimica Acta’s GOLDEN JUBILEE YEAR Sharbil J. Firsan, Editor Aldrichimica Acta [email protected] Dr. S. J. Firsan With this issue of the Aldrichimica Acta, we are pleased to “I really like the Aldrichimica Acta papers. What is special about introduce our readers to the fresh and vibrant new look of them is that they are not only excellent reviews but also typically this venerable journal they have come to value and love. This describe chemistry that can be reproduced, upscaled, and done look weds the traditional successful elements of the Acta with with commercially available reagents and catalysts.” the design principles of the Acta’s new owner, Merck KGaA, — Professor Dr. Benjamin List (Max-Planck-Institut Darmstadt, Germany. This makeover couldn’t have come at a für Kohlenforschung) better time, as we are celebrating the Aldrichimica Acta’s golden “The combination of first hand accounts of scope and limitations jubilee year. While this look is new, I’m happy to assure our and commercially available reagents makes each account contributors and readers that the Acta’s aim will remain the published in Aldrichimica Acta the go-to guide for any chemistry. -
1 Abigail Gutmann Doyle Department of Chemistry
Abigail Gutmann Doyle Department of Chemistry Princeton University 185 Frick Laboratory Princeton, NJ 08544 Phone: 609.258.1944 Email: [email protected] Group website: http://chemistry.princeton.edu/doylelab/ EDUCATION 2003-2008 Harvard University, Department of Chemistry and Chemical Biology Degree awarded: Ph.D., NDSEG, NSF, and Harvard Merit Pre-Doctoral Fellow Research Advisor: Professor Eric N. Jacobsen Doctoral Thesis: Engaging Alkyl Halides and Oxocarbenium Ions in Asymmetric Catalysis. 2002-2003 Stanford University, Department of Chemistry NDSEG Pre-Doctoral Fellow Research Advisor: Professor Justin Du Bois Studies Directed Towards the Hydration of Unactivated Alkenes Catalyzed by Gold Complexes. 1998-2002 Harvard University, Department of Chemistry and Chemical Biology Degree awarded: A.B. and A.M. with Highest Honors, summa cum laude Research Advisor (2000-2002): Professor Eric N. Jacobsen Development of a Synthetically Useful MMO Mimic System for Alkene Epoxidation. PROFESSIONAL AND ACADEMIC EXPERIENCE A. Barton Hepburn Professor of Chemistry, Princeton University (July 2017) Senior Editor, Accounts of Chemical Research (November 2016 to present) Associate Professor of Chemistry, Princeton University (July 2013 to June 2017) • In collaboration with the MacMillan group (Princeton), identified a new cross-coupling paradigm in which the combination of photoredox catalysis and nickel catalysis enables C(sp3)–C bond formation from simple and readily available organic molecules. We described decarboxylative and C–H functionalization of carboxylic acids and anilines with aryl halides to generate valuable amine and ether products. Independent studies by our group have established this activation mode as general for C–H functionalization under exceptionally mild conditions. • Invented new methods for the introduction of 18F into organic substrates that feature uncommonly mild, rapid, and operationally convenient procedures. -
Call for Papers | 2022 MRS Spring Meeting
Symposium CH01: Frontiers of In Situ Materials Characterization—From New Instrumentation and Method to Imaging Aided Materials Design Advancement in synchrotron X-ray techniques, microscopy and spectroscopy has extended the characterization capability to study the structure, phonon, spin, and electromagnetic field of materials with improved temporal and spatial resolution. This symposium will cover recent advances of in situ imaging techniques and highlight progress in materials design, synthesis, and engineering in catalysts and devices aided by insights gained from the state-of-the-art real-time materials characterization. This program will bring together works with an emphasis on developing and applying new methods in X-ray or electron diffraction, scanning probe microscopy, and other techniques to in situ studies of the dynamics in materials, such as the structural and chemical evolution of energy materials and catalysts, and the electronic structure of semiconductor and functional oxides. Additionally, this symposium will focus on works in designing, synthesizing new materials and optimizing materials properties by utilizing the insights on mechanisms of materials processes at different length or time scales revealed by in situ techniques. Emerging big data analysis approaches and method development presenting opportunities to aid materials design are welcomed. Discussion on experimental strategies, data analysis, and conceptual works showcasing how new in situ tools can probe exotic and critical processes in materials, such as charge and heat transfer, bonding, transport of molecule and ions, are encouraged. The symposium will identify new directions of in situ research, facilitate the application of new techniques to in situ liquid and gas phase microscopy and spectroscopy, and bridge mechanistic study with practical synthesis and engineering for materials with a broad range of applications. -
Reactions of Aromatic Compounds Just Like an Alkene, Benzene Has Clouds of Electrons Above and Below Its Sigma Bond Framework
Reactions of Aromatic Compounds Just like an alkene, benzene has clouds of electrons above and below its sigma bond framework. Although the electrons are in a stable aromatic system, they are still available for reaction with strong electrophiles. This generates a carbocation which is resonance stabilized (but not aromatic). This cation is called a sigma complex because the electrophile is joined to the benzene ring through a new sigma bond. The sigma complex (also called an arenium ion) is not aromatic since it contains an sp3 carbon (which disrupts the required loop of p orbitals). Ch17 Reactions of Aromatic Compounds (landscape).docx Page1 The loss of aromaticity required to form the sigma complex explains the highly endothermic nature of the first step. (That is why we require strong electrophiles for reaction). The sigma complex wishes to regain its aromaticity, and it may do so by either a reversal of the first step (i.e. regenerate the starting material) or by loss of the proton on the sp3 carbon (leading to a substitution product). When a reaction proceeds this way, it is electrophilic aromatic substitution. There are a wide variety of electrophiles that can be introduced into a benzene ring in this way, and so electrophilic aromatic substitution is a very important method for the synthesis of substituted aromatic compounds. Ch17 Reactions of Aromatic Compounds (landscape).docx Page2 Bromination of Benzene Bromination follows the same general mechanism for the electrophilic aromatic substitution (EAS). Bromine itself is not electrophilic enough to react with benzene. But the addition of a strong Lewis acid (electron pair acceptor), such as FeBr3, catalyses the reaction, and leads to the substitution product. -
Reactions of Alkenes and Alkynes
05 Reactions of Alkenes and Alkynes Polyethylene is the most widely used plastic, making up items such as packing foam, plastic bottles, and plastic utensils (top: © Jon Larson/iStockphoto; middle: GNL Media/Digital Vision/Getty Images, Inc.; bottom: © Lakhesis/iStockphoto). Inset: A model of ethylene. KEY QUESTIONS 5.1 What Are the Characteristic Reactions of Alkenes? 5.8 How Can Alkynes Be Reduced to Alkenes and 5.2 What Is a Reaction Mechanism? Alkanes? 5.3 What Are the Mechanisms of Electrophilic Additions HOW TO to Alkenes? 5.1 How to Draw Mechanisms 5.4 What Are Carbocation Rearrangements? 5.5 What Is Hydroboration–Oxidation of an Alkene? CHEMICAL CONNECTIONS 5.6 How Can an Alkene Be Reduced to an Alkane? 5A Catalytic Cracking and the Importance of Alkenes 5.7 How Can an Acetylide Anion Be Used to Create a New Carbon–Carbon Bond? IN THIS CHAPTER, we begin our systematic study of organic reactions and their mecha- nisms. Reaction mechanisms are step-by-step descriptions of how reactions proceed and are one of the most important unifying concepts in organic chemistry. We use the reactions of alkenes as the vehicle to introduce this concept. 129 130 CHAPTER 5 Reactions of Alkenes and Alkynes 5.1 What Are the Characteristic Reactions of Alkenes? The most characteristic reaction of alkenes is addition to the carbon–carbon double bond in such a way that the pi bond is broken and, in its place, sigma bonds are formed to two new atoms or groups of atoms. Several examples of reactions at the carbon–carbon double bond are shown in Table 5.1, along with the descriptive name(s) associated with each. -
Aromatic Substitution Reactions: an Overview
Review Article Published: 03 Feb, 2020 SF Journal of Pharmaceutical and Analytical Chemistry Aromatic Substitution Reactions: An Overview Kapoor Y1 and Kumar K1,2* 1School of Pharmaceutical Sciences, Apeejay Stya University, Sohna-Palwal Road, Sohna, Gurgaon, Haryana, India 2School of Pharmacy and Technology Management, SVKM’s NMIMS University, Hyderabad, Telangana, India Abstract The introduction or replacement of substituent’s on aromatic rings by substitution reactions is one of the most fundamental transformations in organic chemistry. On the basis of the reaction mechanism, these substitution reactions can be divided into electrophilic, nucleophilic, radical, and transition metal catalyzed. This article also focuses on electrophilic and nucleophilic substitution mechanisms. Introduction The replacement of an atom, generally hydrogen, or a group attached to the carbon from the benzene ring by another group is known as aromatic substitution. The regioselectivity of these reactions depends upon the nature of the existing substituent and can be ortho, Meta or Para selective. Electrophilic Aromatic Substitution (EAS) reactions are important for synthetic purposes and are also among the most thoroughly studied classes of organic reactions from a mechanistic point of view. A wide variety of electrophiles can effect aromatic substitution. Usually, it is a substitution of some other group for hydrogen that is of interest, but this is not always the case. For example, both silicon and mercury substituent’s can be replaced by electrophiles. The reactivity of a particular electrophile determines which aromatic compounds can be successfully substituted. Despite the wide range of electrophilic species and aromatic ring systems that can undergo substitution, a single broad mechanistic picture encompasses most EAS reactions. -
0900 on Monday, July 13 Through 1700 on Wednesday, July 15, 2020
0900 on Monday, July 13 through 1700 on Wednesday, July 15, 2020 Subarea Topic Speaker Photonic Submillisecond-response Liquid Crystal Spatial Light Shin-Tson Wu Materials Modulators University of Central Florida Photonic Xiong Gong Solution-Processed Infrared Polymer Photodetectors Materials University of Akron Exploration of Carbon-Based Hybrid Nanoarchitectures Photonic Ya-Ping Sun as a Unique Platform for Managing Excited State Materials Clemson University Energies and Processes Aleks Rebane Photonic Femtosecond Laser Induced Macro-Molecular Self- Montana State University Materials Assembly Bozeman Photonic High Detectivity Organic Photodetectors with Bernard Kippelen Materials Ultrabroadband Spectral Response Georgia Tech Jinsong Huang Photonic Grain and Interface Engineering for High Efficiency University of North Carolina, Materials Hybrid Perovskite Solar Cells Chapel Hill Photonic Parag Deotare (YIP) Nanoscale Exciton-Mechanical Systems (NEXMS) Materials University of Michigan Photonic (YIP) Structure-Photophysics-Function Relationship of He Wang Materials Perovskite Materials University of Miami Jason Azoulay Photonic Modular Conjugated Polymers for Mid-Infrared University of Southern Materials Photonic Applications Mississippi Photonic Molecular Engineering Hybrid Perovskite Quantum Xiaodong Xu, Alex Jen Materials Wells for Nanophotonics University of Washington Effects of Redox, Molecular, and Ionic Dopants on the Seth Marder; Henry Snaith Photonic Structure and Electronic Behavior of Haloplumbate Georgia Tech ; University -
Advices for Studying Organic Chemistry
Table of Contents Partial table of contents: Carbon Compounds and Chemical Bonds. Representative Carbon Compounds. An Introduction to Organic Reactions: Acids and Bases. Alkanes and Cycloalkanes: Conformations of Molecules. Stereochemistry: Chiral Molecules. Alkenes and Alkynes I: Properties and Synthesis. Alkenes and Alkynes II: Addition Reactions. Radical Reactions. Alcohols and Ethers. Conjugated Unsaturated Systems. Aromatic Compounds. Reactions of Aromatic Compounds. Aldehydes and Ketones I: Nucleophilic Additions to the Carbonyl Group. Aldehydes and Ketones II: Aldol Reactions. Carboxylic Acids and Their Derivatives: Nucleophilic Substitution at the Acyl Carbon. Amines. Carbohydrates. Lipids. Answers to Selected Problems. Glossary. Index. Solomons/Advices ADVICES FOR STUDYING ORGANIC CHEMISTRY 1. Keep up with your studying day to day –– never let yourself get behind, or better yet, be a little ahead of your instructor. Organic chemistry is a course in which one idea almost always builds on another that has gone before. 2. Study materials in small units, and be sure that you understand each new section before you go on to the next. Because of the cumulative nature of organic chemistry, your studying will be much more effective if you take each new idea as it comes and try to understand it completely before you move onto the nest concept. 3. Work all of the in-chapter and assigned problems. 4. Write when you study. Write the reactions, mechanisms, structures, and so on, over and over again. You need to know the material so thoroughly that you can explain it to someone else. This level of understanding comes to most of us (those of us without photographic memories) through writing. -
Selective Synthesis: New Reagents for Specific Transformations Champery, June 6-9, 2001
CONFERENCE REPORT 732 CHIMIA 2001, 55, No.9 CONFERENCE REPORT Chimia 55 (2001) 732-736 © Schweizerische Chemische Gesellschaft ISSN 0009-4293 Selective Synthesis: New Reagents for Specific Transformations Champery, June 6-9, 2001 Christian G. Bochet* Keywords: CERC3 . Champery . European chemistry' Organic synthesis· Workshop The chairmen of the European Re- from the chiral centers, had a strong im- The day was concluded with the first search Councils' Chemistry Committees pact on the geometry of the dimeric cata- plenary lecture, by Professor Varinder (CERC3) elected organic synthesis as lyst; these effects could be so strong that Aggarwal (University of Bristol, UK). this year's topic for their annual work- similar catalysts varying only by one sub- He explained the asymmetric epoxida- shop, and Switzerland as the host coun- stituent gave opposite enantiomers [1]. tion reaction, in which, instead of using try. The conference chairman, Prof. The afternoon session was concluded the classical strategy (i.e. oxidation of an Philippe Renaud made the excellent by Petri Pihko (The Scripps Research In- alkene), the key step is a carbon-carbon choice of Champery for hosting the stitute, La Jolla, USA), on the synthesis bond forming process (the so-called Co- workshop; the combination of his enthu- of Azaspiracid (Fig. 1), a very potent tox- rey-Chaykovsky epoxidation). The beau- siasm, efficient organization and the in, isolated from Irish mussels. The FGHI ty of this reaction, very simple in its ex- beautiful alpine scenery made this meet- spirocyclic portion proved to be a very perimental realization, is revealed by the ing a really unique event. -
Copyright © 2010 by Shauna M. Paradine ASYMMETRIC HALOFUNCTIONALIZATION of OLEFINS Reported by Shauna M. Paradine April 12
ASYMMETRIC HALOFUNCTIONALIZATION OF OLEFINS Reported by Shauna M. Paradine April 12, 2010 INTRODUCTION The functionalization of olefins is a commonly employed strategy for the rapid construction of molecular complexity in organic synthesis. Since the hybridization change from sp2 to sp3 at the reactive carbon atoms creates new stereocenters, performing these reactions in a well-controlled and highly asymmetric manner is ideal. Development of highly enantioselective olefin functionalization reactions has been a major focus of organic methodology for the past thirty years, and a number of useful and general methods have emerged for the asymmetric epoxidation, dioxygenation, aminooxygenation, hydrogenation, and hydroboration of olefins.1 Although halogen functionality is not as ubiquitous as oxygen and nitrogen in natural products, halogenated natural products still represent a pharmacologically important subclass2 and halogens themselves can be useful for further functionalization.3 The asymmetric addition of halogen functionality onto a carbon framework, therefore, has been of recent interest in synthetic methodology development. Synthetically useful asymmetric methods for the α–halogenation of carbonyls have been developed in response to this challenge,4 but general methods for the highly enantioselective halofunctionalization of olefins has thus far eluded organic chemists. Over the past few years, a number of research groups have developed methods seeking to fill this clear gap in asymmetric synthesis. This recent progress will be presented here. MECHANISTIC AND STEREOCHEMICAL CONSIDERATIONS The electrophilic halogenation of olefins is one of the oldest and most basic transformations in organic synthesis. In fact, “olefin”, which means “oil-forming”, was a term used to describe compounds, typically low molecular weight gaseous alkenes, that became oily liquids upon chlorination.