New Artwork

Thanks to the fabulous Samantha Santana for our new group portrait! We love this new header image (and the way you captured our personalities)!!

Enantioselective Alkynylation of Unstabilized Cyclic Iminium Ions

Weiye Guan, Samantha Santana, Jennie Liao, and Kelci Henninger have developed a highly enantioselective, copper-catalyzed alkynylation of unstabilized cyclic iminium ions (link). This reaction delivers alpha-chiral amine heterocyclic with easily deprotected nitrogen protecting groups. The key was squeezing the chiral pocket by adding ethyl groups to the PyBox ligand. Congratulations to the team for this great method!

Also unveiling Sam’s awesome artwork celebrating Weiye’s discoveries and PhD!

Congratulations, Dr. Jianyu Xu!

Congratulations, Dr. Jianyu Xu, on defending your thesis, “Nickel-Catalyzed Cross-Couplings via Activation of Carbon–Oxygen and Carbon–Nitrogen Bonds!” It was great to celebrate your accomplishments and reminisce on how wonderful it has been to work with you!!

Congratulations, Dr. Weiye Guan!

Congratulations, Dr. Weiye Guan, on defending your thesis, “Catalytic Reactions of Pyridinium and Iminium Ions.” We loved celebrating your accomplishments with a virtual gathering. We wish you all the best in your next position at Adesis! We will miss you!!!

Congratulations, Dr. Megan!

Congratulations, Dr. Megan Hoerrner, on defending your thesis “Nickel-Catalyzed Cross-Coupling Reactions Through C–O and C–N Bond Activation.” This is the 11th PhD defense from the group, and our first one via Zoom videoconference! Best wishes for your next position at Vertex Pharmaceuticals! We miss you!!

Congratulations, Dr. Javon!

Congratulations, Dr. Javon Rabb-Lynch, on defending your thesis “Suzuki–Miyaura Cross-Couplings of Allylic Pivalates to Access All-Carbon Quaternary Stereocenters.” Best wishes for your postdoc at the Naval Research Labs!! We’ll miss you (and all your jokes)!


Our Latest Pyridinium Papers

Congratulations to Megan Hoerrner, Kristen Baker, Corey Basch, and Earl Bampo for their Deaminative Arylation of Amino Acid-derived Pyridinium Salts! This method enables amino acids to be converted to propionic acid derivatives.

Congrats also to Kristen Baker, Diana Lucas Baca, Shane Plunkett, and Mitchell Daneker for their alkyl–alkyl cross-coupling of pyridinium salts with alkyl boranes generated in situ from alkene hydroboration! We submitted this one on Halloween, so Mitchell celebrated with a hot chocolate and dressing as a Dixie cup (see photo).

Reductive Couplings of Alkylpyridinium Salts

In collaboration with Michelle Garnsey, Brian Boscoe, and Joe Tucker at Pfizer, Inc., Jennie Liao, Corey Basch, Megan Hoerrner, and Mike Talley developed a reductive cross-electrophile coupling of alkylpyridinium salts with aryl bromides (link). Congratulations to the team for their great work! Congrats also to Prof. Ruben Martin’s team, who developed a similar reaction (link)!

Alkyl–Alkyl Cross-Coupling Highlighted in OPRD

Group members Shane Plunkett, Corey Basch, and Samantha Santana have developed a Negishi alkylation of alkylpyridinium salts. This is the first example of alkyl–alkyl cross-coupling of alkylpyridinium salts with unactivated alkyl groups. Read it all in their J. Am. Chem. Soc. paper (link). This work was highlighted in Org. Process Res. Dev. Congratulations to this team for a great new reaction!

Congratulations, Dr. Jennie!

Dr. Jennie Liao successfully defended her thesis, “Transition Metal Catalyzed Reactions of Pyridinium and Iminium Ions.” Congratulations, Jennie! We wish you all the best in your new position in Process Discovery Chemistry at Merck. We will miss you!

Feature Article of Our Stereospecific Cross-Couplings

Sarah Pound has elegantly described our efforts to develop efficient, stereospecific cross-couplings of benzylic ammonium salts and benzylic and allylic carboxylates (link). She has also included the inspirations for our work in this area, as well as the important contributions from other groups. Great job, Sarah!

Transforming Amines into Alkenes

Weiye Guan and Jennie Liao have developed conditions to transform amino groups into vinyl groups via benzyl pyridinium intermediates (link). This work is part of a Synthesis Special Topic: Modern Coupling Approaches and their Strategic Applications in Synthesis. Great work, Weiye and Jennie!

Making Di(hetero)arylmethanes from Benzylic Amines

In collaboration with Drs. Michelle Garnsey, Joe Tucker, and Brian Boscoe from Pfizer, Jennie Liao, Weiye Guan, and John Tomlin have developed a method to transform widely available benzylic amines into di(hetero)arylmethanes ( Their strategy uses easily prepared benzyl pyridinium salts, and is broadly tolerant of a wide variety of electron-rich and electron-poor heteroaryl groups. Congratulations to the team!