Project outline: Ubiquitous Suzuki-Miyaura cross-coupling (SMCC) reactions depend on an eclectic array of reaction conditions and experimental variables. Understanding Pd catalyst activation pathway(s), delineating the identity of the active catalyst species, and catalyst deactivation pathway(s), is critical for the development of robust transformations, particularly where side-reactions compete with the desired cross-coupling product. Csp3-Csp2 SMCCs of saturated acyclic and cyclic boronates, including stereospecific variants, with aryl halides, provide connective and powerful ways to access valuable functionalized compounds. Current SMCC methods give modest product yields, requiring high Pd catalyst loadings (5 mol%), which is unattractive from a scale-up perspective. Given the considerable mechanistic knowledge gained about Csp2-Csp2 SMCCs in recent years, we aim to understand more about the Pd catalyst behaviour and speciation in more complicated Csp3-Csp2 SMCCs, based on the best identified Pd-ligand catalyst systems. We aim for full Pd catalyst control, under different reaction conditions and changing experimental variables. Our global aim is to make promising Csp3-Csp2 SMCCs reactions fit for scale-up processes, drawing on mechanistic information, translating our findings to future problematic SMCC chemistry.
Project objectives:
(1) Use High-throughput experimentation (using in-house Chemspeed ISYNTH system) to survey conditions and variables for a series of SMCC reactions.
(2) Analyse reaction outcomes using rich data analysis.
(3) Prepare and characterize novel Pd precatalysts, and assess potential in an array of SMCC reactions, and other complementary cross-coupling reactions.
All Chemistry research students have access to our innovative Doctoral Training in Chemistry (iDTC): cohort-based training to support the development of scientific, transferable and employability skills: https://www.york.ac.uk/chemistry/postgraduate/idtc/
The Department of Chemistry holds an Athena SWAN Gold Award and is committed to supporting equality and diversity for all staff and students. The Department strives to provide a working environment which allows all staff and students to contribute fully, to flourish, and to excel: https://www.york.ac.uk/chemistry/ed/.
You should hold or expect to achieve the equivalent of at least an upper second class degree in Chemistry or a related subject.
For more information about the project, click on the supervisor's name above to email the supervisor. For more information about the application process or funding, please click on email institution
This PhD will formally start on 1 October 2021. Induction activities will start on 27 September.
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