Advanced Organic Chemistry: Introduction to Photoredox Catalysis

In this installment of the Synthesis Workshop Advanced Organic Chemistry course, Dr. Tracy Liu gives us an introduction to photoredox catalysis.
This episode also has an associated problem set available at synthesis-workshop.com/#probl....
References (in order of appearance):
Ischay, M. A.; Anzovino, M. E.; Du, J.; Yoon, T. P. JACS, 2008, 130, 12886. Nicewicz, D. A.; MacMillan, D. W. C. Science, 2008, 322, 77. Narayanam, J. M. R.; Tucker, J. W.; Stephenson, C. R. J. JACS, 2009, 131, 8756.
Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322. D. M. Arias-Rotondo, J. K. McCusker. Chem. Soc. Rev. 2016, 45, 5803. Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 116, 10075.
D. M. Arias-Rotondo, J. K. McCusker. Chem. Soc. Rev. 2016, 45, 5803. Kandoth, N.; Hernandez, J. P.; Palomares, E.; Lloret-Fillol, J. Sustainable Energy Fuels, 2021, 5, 638.
Romero, N. A.; Nicewicz, D. A. Chem Rev. 2016, 116, 10075.
Narayanam, J. M. R.; Tucker, J. W.; Stephenson, C. R. J. JACS 2009, 131, 8756.
Freeman, D. B.; Furst, L.; Condie, A. G.; Stephenson, C. R. J. Org. Lett. 2012, 14, 94 - 97.
Matsui, J. K.; Lang, S. B.; Heitz, D. R.; Molander, G. A. ACS Catal. 2017, 7, 2563. Chan, A. Y., et. al. Chem Rev. 2022, 122, 1485.
Tellis, J. C.; Primer, D. N.; Molander, G. A. Science 2014, 345, 433.
Zuo, Z.; Ahneman, D. T.; Chu, L.; Terrett, J. A.; Doyle, A. G.; MacMillan, D. W. C. Science 2014, 345, 437.
JACS 2015, 137, 4896.
Privileged Ni ligand scaffolds: Diccianni, J. B.; Diao, T. Trends in Chemistry, 2019, 1, 830.
Lipp, A.; Badir, S. O.; Molander, G. A. ACIE, 2021, 60, 1714.
Zhang, P.; Le, C. C.; MacMillan, D. W. C. JACS 2016, 138, 8084.
Le, C.; Liang, Y.; Evans, R. W.; Li, X.; MacMillan, D. W. C. Nature 2017, 547, 79.
For additional examples of indirect HAT photoredox: Capaldo, L.; Ravelli, D. Eur. J. Org. Chem. 2017, 2056.
Cao, H.; Tang, X.; Tang, H.; Yuan, Y.; Wu, J. Chem. Catalysis, 2021, 1, 523.
For a review covering decatungstate chemistry from 1980s to early 2000s: Tzirakis, M. D.; Lykakis, I. N.; Orfanopoulos, M. Chem. Soc. Rev. 2009, 38, 2609.
Science 2022, 378, 383.
For reviews on photophysics and synthetic applications: Ravelli, D.; Fagnoni, M.; Fukuyama, T.; Nishikawa, T.; Ryu, I. ACS Catal. 2018, 8, 701. Capaldo, L.; Ravelli, D.; Fagnoni, M. Chem Rev. 2022, 122, 1875.
For reviews on PCET Photoredox chemistry: Hoffmann, N. Eur. J. Org. Chem. 2017, 1982.
Murray, P. et. al. Chem Rev. 2022, 122, 2017.
Merck/MacMillan Photoredox Catalyst Chart (visit MacMillan Lab website). DiLuzio, S.; Connell, T. U.; Mdluli, V.; Kowalewski, J. F.; Bernhard, S. J. Am. Chem. Soc. 2022, 144, 1431. Singh, A.; Teegardin, K.; Kelly, M.; Prasad, K. S.; Krishnan, S.; Weaver, J. D. J. Organomet. Chem. 2015, 776, 51.
HOMO-LUMO locations of homo and heteroleptic Ir photocats: JACS 2003, 125, 7377; Chem. Mater. 2005, 17, 5712;
JACS 2021, 143, 1179.
Zou, Z.; MacMillan, D. W. C. JACS 2014, 136, 5257.
Stern-Volmer in Flow: Kuijpers, K. P. L.; Bottecchia, C.; Cambie, D.; Drummen, K.; Konig, N. J.; Noel, T. J. ACIE 2018, 57, 11278.
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ACS Cent. Sci. 2020, 6, 2053.
Chem. Rev. 2016, 116, 10075.
Science 2021, 374, 1258.
Chem. Rev. 2022, 122, 2752.

[@KhadeijaAbd92]

What clear explanation ❤

[@dowonahn6714]

What wonderful explanation! Thanks!😁

[@go_yixiong]

Nice! Well done!💯

[@shubhamdhal589]

Nice explanation.

[@ligmabaldrich485]

Been waiting for this video for a while - thanks for the well-explained lecture!!

[@aidanlooby]

Great video! Well done to Tracy!

[@siddheshbachhav7430]

Thank you...

[@UniCorneliusfan21]

Light magic
I think I’m gonna need a course on stereoselectivity of some reactions e.g metal allylations etc.

[@Fili229]

At 23:40 You lost an oxygen atom in the cycle