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  • Group photo fall 2023. Back row, left to right: Tyler, Anthony, Sam, Ben. Middle row, left to right: Sophie, Terry, James, John. Front row, left to right: Alex, Katie, Brian, Josh. Front front row: Tiny Tyler.
  • The group standing in front of Lash Miller. Back row, left to right: Sophie, James, John, Prath, Anthony, Alex, Tyler, Brian, Ben. Front row, left to right: Sam, Jelena, Katie, Tiny Tyler, Josh, Vincent.
  • Group photo fall 2022. Back row, left to right: Sophie, John, Prath, Anthony, Ben, Tyler, Sam D., Bianca. Front row, left to right: Tiny Tyler, James, Sam C., Alex, Katie, Eun Seo, Josh, Jamieleen.

Welcome to Rousseaux Group

Our group is interested in the development of new methodologies to address current limitations and explore new areas in catalysis and synthetic organic chemistry. Our research involves aspects of nickel catalysis, homoenolate chemistry, and transnitrilation strategies.
 
If you are interested in joining our lab, please contact Prof. Rousseaux at sophie.rousseaux@utoronto.ca. Potential graduate students are also encouraged to visit the Department of Chemistry website for further information.

Announcements

Our new publication on the photocatalytic O- to S-rearrangement of tertiary cyclopropanols has been published in Angewandte Chemie.  Congratulations to John & James for their innovative work developing this chemistry! 

After spending a summer at Genentech, Eun Seo publishes a strategy to synthesize benzylamines from (hetero)aryl halides and glycine-derived N-hydroxyphthalimide esters in Synlett! Fantastic work from one of our undergraduate students! 

Our first publication of the year is out in The Journal of Organic Chemistry! We report the Ni-catalyzed reductive arylation of redox-active esters for the synthesis of alpha-aryl nitriles, including investigations of a key chlorosilane additive. This project kick started the NHP explorations within our group and laid the groundwork for our mechanistic understanding of this chemistry. Congratulations to Nick & Alex!

A huge congratulations to Dr. Tyler McDonald for successfully defending his doctoral thesis! Tyler is the fifth PhD graduate from the group and was a key contributor to the development of the small ring research program, including chemistry of homoenolates as well as the synthesis of small borylated carbocycles. He also spearheaded the Alberta contigent of the group and was a champion for western Canada. Tyler is off to Yale in January to begin a postdoctoral position in the Miller group. Best of luck Tyler!

Our new review on redox-active thiocarbonyl auxiliaries in Ni-catalyzed cross-couplings of aliphatic alcohols appears in Accounts of Chemical Research. Congratulations to John on this stupendous review!

Our new publication on the asymmetric Cu(I)-catalyzed conjugate borylation of unsaturated acyl silanes has appeared in Synlett! Congratulations to Anthony, Bianca, Sam, and Brian on this great synthetic paper! 

  

Our new publication on Ni-catalyzed reductive hydrocyanation of alkynes using malononitrile and a fomaldehyde additive appears in JACS! This paper features some amazing mechanistic studies by Anthony & Ben. Fantastic work, congratulations to both of you! 

After Sophie receives tenure in July 2022, the tenure party is finally held in August 2023! Past and present graduate students gather to celebrate this incredible milestone. A huge (belated) congratulations to Sophie for this well-deserved achievement!  

Our new book chapter on the asymmetric synthesis of cyclopropane and cyclobutane-containing small molecule pharmaceuticals is out in Reference Module in Chemistry, Molecular Sciences and Chemical Engineering. Excellent work John! Look out for this chapter in Comprehensive Chirality, 2nd Edition in 2024!

Our latest review covering metal-catalyzed C–C bond formation at cyclopropanes has been published in Nature Reviews Chemistry. Congratulations to Katie & Alex! 

We say a sad goodbye to our 2022/2023 undergraduate students. Best of luck in your future endeavors to Bianca, Eun Seo, Jamieleen, and Sam! We also welcome two summer undergraduate students, Vincent and Jelena. Brian Doan also joins the group for the Summer Research Program after completing his MSc at York University. Welcome all, we're excited to have you!

Our first paper of the year describing the synthesis of 3-borylated cyclobutanols from epihalohydrins or epoxy alcohol derivatives is now out in Chemical Science. A big congrats to Tyler on this stupendous paper! 

Our new publication detailing the reductive coupling of (hetero)aryl halides with the redox-active esters of cyclopropylamines (and other small rings!) has been published in Organic Letters! This project was a collaboration with Genentech. Superb job, Mike and Alex! 

A huge congratulations to Dr. Mike West who successfully defended his thesis in September 2022! Mike is the fourth PhD student of the group and has been a champion of small rings. He has conducted field-leading work in the areas of cyclopropanol, cyclopropylamine, and homoenolate chemistry. Mike has accepted an industrial postdoctoral position with Merck & Co. in New Jersey. Best wishes Mike, we can't wait to see what the future holds for you!

The group welcomes our newest graduate student, Sam Dudra. Sam has joined the group as an MSc student. Welcome Sam! Jamieleen and Eun Seo join the group as ROP students and Bianca joins as a CHM499 student. Samantha Chan also continues on in the group as a CHM499 undergraduate student. We're excited to have you all!

Mike's cover design based on his recent publication for the synthesis of 1- and 1,2-substituted cyclopropylamines appears in Organic Letters! Great work putting that together Mike! 

Our new perspective article based on a recent publication by the Nagib lab for the synthesis of carbenes from alkyl and aryl aldehydes appears in Science. Take a look at the paper and the perspective! Well done writing this perspective, Mike.

Our new paper describing the synthesis of 1- and 1,2-substituted cyclopropylamines from ketone homoenolates has been published in Organic Letters and is also selected to be featured on the cover of the issue! Well done Mike and Julia. 

The group attends the Canadian Chemistry Conference and Exhibition (CCCE) 2022 in Calgary, Alberta. Alex, Mike, and Anthony give oral presentations and Josh and Tyler give poster presentations. Alex receives a presentation award. Well done all!

We're happy to have our newest member Prath (MSc student) join the group. After completing his undergraduate degree, Ben continues his research in the group as a PhD student. Welcome both of you to the graduate program! Patricia and Samantha also join the lab as NSERC USRA summer students. 

Our new paper describing the Ni-catalyzed alpha-arylation of secondary amides using redox-active esters has been accepted in Organic Letters. This work was completed in collaboration with Merck & Co. Great job Alex & Nick! 

Our first new paper of the year describing the decyanation–(hetero)arylation of malononitrile derivatives has been accepted in Organic & Biomolecular Chemistry. Fantastic work Reggie and Purvish!

To finish the year, our new paper sharing the Ni-catalyzed synthesis of thiocarboxylic acid derivatives is accepted in Organic Letters. Congrats to John, Katie, and Reggie!

  • Alex and John both receive the 2021–2022 Adrian Brook Graduate Scholarship in Organic Chemistry. Congrats to both of you!
  • The group presents at QOMSBOC 2021 (Dec 3–4). Alex gives an oral presentation while Mike, Tyler, John, and Josh give poster presentations. Alex and Mike both receive presentation awards. Great job everyone!
  • Alex also represented the group and UofT during the Aldrich Canadian Chemsitry Symposium (Dec 9th).

   Our new paper describing the Ni-catalyzed C(sp3)–O arylation of α-hydroxy ester derivatives has been accepted in Organic Letters. This paper was also selected to be featured as an "ACS Editors Choice". Superb work John!

The group send big congratulations to Dr. Purvish Patel and Dr. Nick Michel who successfully defended their theses! Purvish is the second PhD student of the group and has helped shape the group's interests in nickel catalysis and transnitrilation methodologies. Nick is the third PhD student of the group and has been impactful in his work with nickel catalyzed cyanation and arylation strategies. Both Purvish and Nick have taken their talents to Paraza Pharma in Montreal. We'll miss you Purvish and Nick, but we know you're both off to do great things!

We're happy to have our newest member Joanna (PhD student) join the group. Also, after completing his summer NSERC USRA, Ben continues his research as a CHM499 student – welcome both of you!

Members of the group "attend" the virtual Canadian Chemistry Conference and Exhibition 2021. Purvish, Tyler, and John give oral presentations while Mike and Alex give poster presentations. John was awarded third place for the NACS Student Catalysis Presentation Award and Mike was awarded second place for the Organic Division Graduate Poster Competition. Terrific job everyone! 

We're excited to have a new student James (PhD student) join the lab after completing his MSc at the University of Alberta - welcome to the group James!

Our new paper showcasing the design of an electron-withdrawing benzonitrile ligand for Ni-catalyzed cross-coupling has been accepted in JACS. Great work Reggie & Racquel! 

Tyler passes his Departmental Oral Exam and becomes the group's newest PhD Candidate. Great work Tyler!

We're excited to have new students Katie (PhD student) and Ben (NSERC USRA) join the lab - welcome both of you!

John has been awarded an NSERC CGS-D scholarship, Alex has been awarded an NSERC PGS-D scholarship, and Julia has been awarded an NSERC CGS-M scholarship. Congratulations to everyone, fantastic work!

A big congratulations to Dr. Reggie Mills who successfully defended his thesis in December 2020! Reggie was the first PhD student of the group and he helped lay the foundation for numerous advances into cyclopropanol and homoenolate chemistry, transnitrilation strategies, and nickel-catalyzed reactions. His work will no doubt have a long-lasting impact on the group. Reggie has taken his talents to Princeton University to be a Postdoctoral Researcher in the Chirik Group. Best wishes Reggie, we can't wait to see what the future holds for you!

  • We say a heartfelt goodbye to Racquel who graduates with a MSc degree. Congratulations Racquel on all your hard work and good luck in your future endeavours - we'll miss you!
  • Our review on the selective carbon-carbon bond cleavage of cyclopropanols has been accepted in Chemical Reviews. Congratulations to Tyler, Reggie, and Mike on this accomplishment!

  • A big welcome to our newest group members Alex Gabbey & Julia Pia - we're excited to have you join us!
  • Our paper on the boronic acid-mediated ring-opening and Ni-catalyzed arylation of 1-arylcyclopropyl tosylates has been accepted in Chemical Communications. Great work Reggie and John!

  • Our paper,  in collaboration with the Aspuru-Guzik group, on the development of a redox-active leaving-group for cyclopropanol C(sp3)–O arylation has been accepted in JACS. Congratulations to Reggie, John and Gabe!

  • The lab reopens after a >3-month shutdown due to COVID-19. Stay safe everyone!
  • We say goodbye to Piers St-Onge (CHM 499 student). Congratulations on completing your undergraduate degree!
  • Congratulations to Mike, Tyler, and Anthony, who have received NSERC doctoral awards to support their graduate studies!
  • Purvish returns from a 4-month internship at Inception Sciences and Repare Therapeutics in Montreal. Welcome back Purvish!
  • We say goodbye to Julia who has completed her co-op placement in our lab. 
  • Our paper on the Ni-catalyzed reductive cyanation of aryl halides has been accepted in JACS. Congratulations to Reggie, Josh and Purvish!

 

  • The group attends the 2019 QOMSBOC conference hosted by the University of Ottawa. Reggie, Nick, Racquel, Tyler and Josh give poster presentations. Mike gives an oral presentation. Well done everyone!

September 2019 - Welcome to our new group members: Anthony Palermo (PhD student), Piers St-Onge (CHM 499 student) and Julia Ju (SEE UofT Co-op Student).

September 2019 - Mike passes his Departmental Oral Exam. Congrats Mike!

June 2019 - Welcome to new graduate student, John Monteith, who joins the group as part of the Summer Research Program. 

May 2019 - Our paper detailing the synthesis of nitrile-bearing quaternary centers via an equilibrium-driven transnitrilation and anion-relay strategy has been accepted in Angewandte Chemie. Awesome work Seb, Mike, and Purvish! 

May 2019 - Our work featuring the synthesis of malononitrile derivatives through the transnitrilation and anion-relay strategy has been accepted as an invited paper in Tetrahedron. Great work Reggie!

May 2019 - Welcome to our newest members: Josh Graham as part of the Summer Research Program and Emmanuel Fagbola as a NSERC USRA student!

April 2019 - Nick has been awarded an NSERC CGS-D scholarship and Tyler has been awarded the NSERC CGS-M scholarship. Big congratulations to both! 

March 2019 - Our work detailing the synthesis of nitrile-bearing quaternary centers via an  equilibrium-driven transnitrilation and anion-relay strategy is now available on ChemRxiv.

Contact Info

Department of Chemistry
University of Toronto
80 St. George St.
Toronto, Ontario  M5S 3H6
Canada  
 
Email: sophie.rousseaux@utoronto.ca
Phone:  416-978-4198
Room:  DB 475