#  Max Tishler Prize Lecture: Jin-Quan Yu (Scripps) 

 



####  calendar\_today Date and Time 

 **October 2, 2023** 

 04:15PM - 05:15PM EDT 

####  pin\_drop Location 

 **Pfizer Lecture Hall**  



 

 



 

 Title: 20-Year Dancing with Palladium and C–H bonds: From Curiosity to Industrialization

   
Part I: Reactivity and Enantioselectivity; Part II: Site-selectivity and Sustainability

 The widespread presence of C–H bonds at various sites of synthetic substrates renders C–H activation the most powerful platform for developing catalytic reactions for synthesis. To realize the full potential of C–H activation for synthesis, four fundamental challenges must be addressed: developing diverse carbon-carbon and carbon-heteroatom bond forming reactions of diverse poorly reactive native substrates (ReactivitY); enantioselective C–H activation reactions via asymmetric metalation of C–H bonds (EnantioselectivitY); site selective metalation and functionalization of remote C–H bonds (Site-selectivitY); achieving catalytic cycles using sustainable oxidants such as molecular oxygen, aqueous hydrogen peroxides as the terminal oxidants (SustainabilitY). Despite century-long efforts, seeking solutions to these problems has met with limited success due to a fundamental challenge: lack of ligands that can accelerate C–H activation reactions.  
By combining the weak coordination (entropy) from substrates and ligand acceleration (enthalpy), we have made substantial progress towards addressing these four challenges. Most notably, six generations of bi-functional ligands (MPAA, APAQ, APAO, MPAAm, MPAThio, Pyridine-Pyridone) have been developed to enable a wide range of enantioselective1-6 and site-selective7-14 C–H activation reactions of diverse classes of native substrates. In parallel, we have realized C–H hydroxylation using molecular oxygen or aqueous hydrogen peroxide as the terminal oxidants, paving the way for large-scale industrialization.11,12 Most recently, we have extended site-selective C–H activation to multiple methylene C–H bonds for ring formation through a stitching strategy.15

   
(1) Shi, B.-F. et al. Angew. Chem., Int. Ed. 2008, 47, 4761. (2) Chu, L. et al. Science, 2014, 346, 451. (3) Zhang, F.-L.; Hong, K. et al. Science, 2016, 351, 252. (4) Chen, G.; Gong, W. et al. Science, 2016, 353, 1023. (5) Wu, Q.-F. et al. Science 2017, 355, 499. (6) Saint-Denis, T. G. et al. Science 2018, 359, 759. (7) Leow, D.; Li, G. et al. Nature 2012, 486, 518. (8) Wang, X.-C. et al. Nature 2015, 519, 334. (9) Zhang, Z.; Tanaka, K.; Yu, J.-Q. Nature 2017, 543, 538. (10) Shi, H. et al. Nature 2018, 558, 581. (11) Li, Z.; Wang, Z. et al. Science 2021, 372, 1452. (12) Wang, Z. Hu, L. et al. Science 2021, 374, 1281. (13) Chan, H. S. et al. Science 2022, 376, 1481. (14) Kang, G. et al. Nature 2023, 618, 519. (15) Yang, J.-M. et al. Science 2023, 380, 639.



 



 

 



 

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