Shane, Corey, and Samantha’s alkyl–alkyl cross-coupling of alkyl pyridinium salts was highlighted in Synfacts. Thank you to Prof. Paul Knochel and Ferdinand H. Lutter for describing our work!
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)!
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!
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!
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!
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!
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 (https://pubs.acs.org/doi/10.1021/acs.orglett.8b01062). 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!
Our paper, “Harnessing Alkyl Amines as Electrophiles for Nickel-Catalyzed Cross Couplings via C–N Bond Activation” is one of the Top 20 most downloaded JACS articles for the previous 12 months! Check it out: https://pubs.acs.org/action/showMostReadArticles?topArticlesType=recent&journalCode=jacsat
Congratulations, Dr. Corey Basch! Dr. Basch defended his thesis, “Nickel-Catalyzed Cross-Couplings via Activation of Alkyl Carbon–Nitrogen Bonds” with spectacular success! Corey established alkyl pyridinium salts as effective electrophiles for cross-couplings. We will miss you, and wish you the best in your postdoc with Prof. Tom Rovis!
Congratulations to Kelsey Cobb, Javon Rabb-Lynch, Megan Hoerrner, Alex Manders, and Qi Zhou on their recent development of a stereospecific Suzuki–Miyaura cross-coupling of allylic pivalates to set all-carbon quaternary stereocenters (http://pubs.acs.org/doi/full/10.1021/acs.orglett.7b02063)! This reaction is enabled by a simple nickel/BISBI catalyst system, and enables efficient formation of allylic products with internal alkenes.
Corey, Jennie, Jianyu, and Jake’s cross coupling of alkyl amines is featured on Design for Science. Read it here: http://d4sci.com/activating-carbon-nitrogen-bonds-alkyl-amines-as-alkylating-agents/