Redox-Paired Alkene Difunctionalization Paper – Now Online in JACS

The final version of our redox-paired alkene difunctionalization paper appears online today in J. Am. Chem. Soc. In this study, we outline a novel redox paradigm for alkene difunctionalization in which an oxidative difunctionalization process is coupled to a reductive difunctionalization process without any additional terminal oxidants or reductants. The unique mechanism of this reaction involves a PdII/PdIV/PdII/PdIV catalytic cycle, as elucidated through experiment and computations. Congrats to the entire project team, and thanks to our collaborators Prof. Ken Houk from UCLA and Prof. Peng Liu from the University of Pittsburgh.

For a link to the paper in J. Am. Chem. Soc., click here:

As a reminder, a pre-print of this work was deposited at the end of 2022:

Latest Pre-Print Describes a Unique Sigma-Bond Annulation Process

The newest method to emerge from the group builds on our interest in developing catalytic strong activation reactions via β-X elimination. We have previously demonstrated that PdII(π-olefin) intermediates generated in this manner can be engaged in nucleopalladation / protodepalladation sequences to effect functional group metathesis of an outgoing C(sp3)–X (X = C, N, O, F, etc.) for a new C(sp3)–C or C(sp3)–N. In our newest pre-print, Hui-Qi, Jing-Chen, and collaborators from Pfizer extend the reach of this approach, demonstrating annulation of transiently generated PdII(π-olefin) intermediates via β-X elimination. In terms of synthetic planning, the reaction allows conversion of simply aliphatic alcohol, amine, and thiol compounds into valuable heterocyclic products. Especially exciting applications are in amino acid upgrading and heterocycle transfiguration. Congrats to the team!

For a link to the pre-print in ChemRxiv, click here:

New visiting student Xiaowei joins the lab!

We have a new undergraduate intern Xiaowei Chen visiting from Rice University. Xiaowei previously worked in the group of Prof. Julian West on ligand-to-metal charge transfer photocatalysis. She joins the lab as an AYRIU scholar and will be working with Anne to explore nickel catalysis. Welcome to the group, Xiaowei!

Asymmetric Reductive Heck Hydroalkenylation and Hydroalkynylation – Now In Press in Angewandte Chemie

Appearing online today in Angewandte Chemie International Edition, we describe the most recent findings from our program in dual catalytic enantioselective alkene functionalization via a transient directing group strategy. Specifically, we developed a method for hydroalkenylation and hydroalkynylation of alkenyl aldehydes that is enabled by reversible condensation of tert-leucine. Together with the lab of Prof. Peng Liu at the University of Pittsburgh, we applied density functional theory to elucidate the structural features of the amino acid co-catalyst that lead to high catalytic efficiency and high enantioselectivity. Congrats to the entire project team!

For a link to the paper, click here:

As a reminder, a pre-print of this work in summer 2022: