(542e) Development of a Continuous Stirred-Tank Reactor (CSTR) Platform for Handling Heterogeneous Visible-Light Photoredox Reactions

Authors: 
Nandiwale, K. - Presenter, Massachusetts Institute of Technology
Pomberger, A. - Presenter, Massachusetts Institute of Technology
Mo, Y. - Presenter, Massachusetts Institute of Technology
Jensen, K. F., Massachusetts Institute of Technology
Robinson, R. I., Novartis Institutes for BioMedical Research
Duvadie, R., Novartis
Visible-light photoredox has been demonstrated to be a powerful synthetic methodology to access pharmaceutical related compounds. However, most of the photoredox reactions involve insoluble starting materials or products which makes it challenging to be implemented in a continuous flow reactor. Here we present a new solid-handling platform for heterogeneous photoredox reaction systems in flow, which integrates a newly designed solid-feeding strategy and a continuous stirred-tank reactor (CSTR) cascade. The residence time distribution for single phase and solids was measured to characterize the hydrodynamics of the heterogeneous flow in the CSTR cascade. Silyl radical-mediated metallaphotoredox cross-electrophile coupling reactions was demonstrated with an inorganic base as the insoluble starting material. Multigram synthesis was achieved within 24 hours of stable operation without any human intervention.