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 VIRTUAL 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 and Secondary Fair are going to be hosted online, more details to follow!
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 and Secondary Fair are going to be hosted online, more details to follow!
Go here for more information and to sign up!!
January 2021: The Wengryniuk Lab welcomes new first year student Angelika Baran!
Welcome to the team!
Welcome to the team!
Breaking News and Events
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April 12, 2021: Andres, Jen, Tony, and Xiao's first report on N-HVI mediated Heterocyclic Group Transfer or "HGT" entitled "Heterocyclic group transfer reactions with I(III) NHVI reagents: access to N-alkyl(heteroaryl)onium salts via olefin aminolactonization" has been accepted for publication in Chem. Sci.: https://doi.org/10.1039/D1SC00187F!
This work represents our first report on this exciting new direction for the W lab! While it may have been on Chem Rxiv for a little while now, this final report features an expanded substrate scope and a more complete picture of our platform for the synthesis of complex (heteroaryl)onium salts with N-HVIs. These salts are a versatile and emerging functional handle for organic chemistry, spanning heterocycle synthesis to radical precursors for cross coupling. With all the exciting new chemistry emerging around pyridinium salts, there has been little innovation around how we make them, and that is where we come in. Using N-HVIs, we have a highly modular and general toolkit for introducing these functional handles. In this report, we look at an "aminolactonization" from simple alkenoic acids, using in situ generated N-HVIs and operationally simple conditions. With this under our belt, we have a lot of exciting new projects underway in the group looking at sticking pyridinium salts anywhere your heart desires on organic molecules. Be sure to check it out and stay tuned!!! January 12, 2021: Xiao's Synpacts article examining the regioselective synthesis of Ortho-Quinones and Ortho-Quinols from Phenols using I(V) Reagents is up on Synlett!
This Perspective was an invited submission following up on our ACIE paper in 2019 on dearomatization using our I(V) Bi(N)-HVI reagents (Check that out here!). It highlights the unique utility of I(V) reagents for the regioselective ortho-oxidation of phenols, covering everything from reagent and methods development to total synthesis applications! |
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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!
