The W Lab, Spring Graduation 2019
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The W Lab @ TempleOur lab aims to develop a multifaceted research program that leverages a unique class of hypervalent iodine reagents in novel approaches to "umpolung" or reverse-polarity chemistry, Our research encompasses reagent development, new synthetic methods, and the application of these tools to the synthesis of natural products containing challenging medium-ring heterocycles. We aim to bridge the gap between the three-dimensional molecular complexity of nature and the planar aromatic structures of small molecule libraries by introducing simplified strategies and novel disconnections of these valuable architectures.
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W Lab News
The Wengryniuk Lab will yet again be participating as judges at the George Washington Carver Science Fairs this year!
Want to join us for a fun filled day of talking to kiddos about science and fostering excitement in STEM??
Elementary Fair is February 19 at the Academy of Natural Sciences and Secondary Fair is March 3rd at Temple.
Go here for more information and to sign up!!
Want to join us for a fun filled day of talking to kiddos about science and fostering excitement in STEM??
Elementary Fair is February 19 at the Academy of Natural Sciences and Secondary Fair is March 3rd at Temple.
Go here for more information and to sign up!!
January 2020: The Wengryniuk Lab welcomes new first year students Bill Motsch and Alexi Martin!
Welcome to the team!
Welcome to the team!
Breaking News and Events
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January 3, 2020: Felipe and Wendy's paper entitled "Direct C–H alpha-Arylation of Enones with ArI(O2CR)2 Reagents" has been accepted for publication in JACS: https://doi.org/10.1021/jacs.9b11282)!
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This work outlines a novel approach to the direct C–H alpha-arylation of enones, a remaining challenge in organic synthesis. Alpha-aryl enones are valuable structural motifs and synthetic intermediates, however, perhaps surprisingly in the age of C–H functionalization, there remains no general strategy for the direct enone C–H arylation. By leveraging the unique reactivity of in situ generated b-pyridinium silyl enol ethers, Felipe and Wendy developed an arylation strategy using readily accessible ArIX2 reagents which proceeds via a reductive [3,3]-iodonium Claisen. A particularly powerful feature of this chemistry is that the entire aryl iodide moiety is transferred intact, making it highly atom economical and installing a valuable functional handle for downstream manipulations. This work builds on recent beautiful work from Shafir by extending arylative iodonium Claisen reaction to non-malonate derivatives and appears to be enabled by dual steric and electronic modulation by the beta-pyridinium moiety. This unique reactivity is the subject of ongoing investigations in our group. Congrats to Felipe (Y4) and Wendy (Temple Undergrad!) on some great work!
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August 19, 2019: Xiao and Nate's paper entitled "Dearomatization of Electron-Deficient Phenols to ortho-Quinones Enabled by Bidentate Nitrogen-Ligated I(V) Reagents" has been accepted for publication in Angewandte Chemie: DOI: 10.1002/anie.201909868.
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This work provides the first general synthetic method for the oxidation of electron-deficient phenols, substrates that have remained elusive as they are inert to common oxidants. The resulting ortho-quinones represent valuable synthetic building blocks for complex molecule synthesis and we showcase several methods for their one-pot derivatization. Building from our lab's work with I(III) N-HVIs, this work relies on a class of bidentate nitrogen-ligated I(V) reagents, or Bi(N)-HVIs, and represents their first synthetic application. Beyond the enhanced reactivity of these Bi(N)HVIs, the presence of a bidentate nitrogen ligand results in a much more tunable platform for the design and development of I(V) reagents which our laboratory is continuing to pursue! Stay tuned!!
