Author: tyoon

Fe-mediated decarboxylative coupling

Grace and Sam’s magnum opus on Fe(III)-mediated photochemical couplings of carboxylic acid feedstocks is published in Chem. This is the second installment in a productive collaboration with Scott Bagley and Mark Bundesmann at Pfizer.

NSF awards

Congratulations to Alana and Cade for receiving an NSF GRFP Award and Honorable Mention, respectively! These awards are increasingly competitive, and we’re incredibly proud of everyone who applied.

Transitions

This month has a lot of transitions for the group. We welcome Alana, Matthieu, and Max as new first-years in the group, and GM as a new undergraduate researcher.  We also bid fond farewells to PhD recipient Sam (Yoon lab PhD #23), MS degree recipient Meredith, and undergraduates Guy and Alisha.

TA spectroscopy for photocatalytic synthesis

TA spectroscopy can provide detailed insight into the mechanisms of photocatalytic reactions. Read Wes’ tutorial review in this year’s Specialist Periodical Reports – Photochemistry.

Cross-ketonization

Andrew developed a method to selectively combine two different carboxylic acid feedstocks into unsymmetrical ketones using a metallaphotoredox strategy. The result is a modern take on the industrial process of acid ketonization, updated for complex molecule synthesis. This project was born out of a pandemic brainstorm, and we’re pleased to see it online today at …

Uncontrolled Sensitization in Asymmetric Photocatalysis

Steven worked with Zeb Girvin (Miller group), Laura Cotter and Hyung Yoon (Mayer group) in a fun three-lab collaborative project on asymmetric [2+2] photocycloadditions of acyclic vinylpyiridines, now up at JACS. The reaction involves an unusual mechanism for an asymmetric excited-state photoreaction where the chiral catalyst influences the rate of a step after the initial …

LED-NMR + RPKA

LED-NMR is a data-rich analytical tool that is suitable for modern RPKA techniques. In studing an enantioselective photocatalytic reaction, Wes and Steven found that LED-NMR RPKA enabled determination of rate laws in a fraction of the time that conventional initial-rate kinetics could. In the process, they uncovered a surprising change of reaction mechanism as a …

Cooperative Photocatalytic Stereocontrol

In the process of developing an enantioselective [2+2] photocycloaddition of vinylpyridines, Steven and Wes discovered stereochemical cooperativity between a chiral Brønsted acid catalyst and a chiral Ir photocatalyst. It’s a gratifying demonstration that matched/mismatched effects are just as important in excited-state reactions as in classical ground-state reactions. Thanks also to Christine Le and Dean Toste …

Cu-mediated Decarboxylative Coupling

The Yoon lab’s first publication of 2022 is a new oxidative decarboxylative coupling process based on the intrinsic photochemistry of Cu(II) carboxylate complexes. Check out the paper in Nature Chemistry. Congratulations Yukki, Sam, Grace, Kimberly, and our great team of collaborators at Pfizer! For a video walkthrough of how to set up this reaction, as …

Chiral Photocatalyst Review

How have photochemists approached the design of chiral photocatalysts? Matt, Jesse, and Wes have thoughts in their new comprehensive review in Chem Rev.