Synthesis Workshop: Radical Polar Annulation Reactions with Dr. Christopher Kelly (Episode 98)

In this Research Spotlight episode, Dr. Christopher Kelly (Scientist, Discovery Process Research, Janssen) joins us to take us into the field of radical polar annulation reactions (RPARs).

Key references:
Org. Synth. 2017, 94, 16.
https://doi.org/10.15227/orgsyn.094.0016
J. Am. Chem. Soc. 2018, 140, 8037.
https://doi.org/10.1021/jacs.8b05243
Org. Lett. 2018, 20, 6840.
https://doi.org/10.1021/acs.orglett.8...

Other references (in order of appearance):
Zard, S. Z. Org. Lett. 2017, 19, 1257.
Shaw, M. H.; Twilton, J.; MacMillan, D. W. C. J. Org. Chem. 2016, 81, 6898.
Roth, H. G.; Romero, N. A.; Nicewicz, D. A. Synlett, 2016, 27, 714.
Pitzer, L.; Schwarz, J. L.; Glorius, F. Chem. Sci., 2019, 10, 8285; Wiles, R. J.; Molander, G. A. Isr. J. Chem. 2020, 60, 281; Guo, W.; Cheng, H.-G.; Chen, L.-Y.; Xuan, J.; Feng, Z.-J.; Chen, J.-R.; Lu, L.-Q.; Xiao, W.-J. Adv. Synth. Catal. 2014, 356, 2787.
Matsui, J. K; Lang, S. B.; Heitz, D. R.; Molander G. A. ACS Catal. 2017, 7, 2563.
Reviews on cyclopropanes and their syntheses: Pellissier, H. Tetrahedron 2008, 64, 7041; Wessjohann, L. A.; Brandt, W.; Thiemann, T. Chem. Rev. 2003, 103, 1625; Ebner, C.; Carreira, E. Chem. Rev. 2017, 117, 11651. CF3 cyclopropanes as isosteres: Barnes-Seeman, D. et al ACS Med. Chem. Lett. 2013, 4, 514; Lazerwith, S. E. et al J. Med. Chem. 2014, 57, 1893.
Reviews on perfluoroalkyl-substituted cyclopropanes and their syntheses: Grygorenko, O. O.; Artamonov, O. S.; Komarov, I. V.; Mykhailiuk, P. K. Tetrahedron 2011, 67, 803; Bos, M.; Huang, W.-S.; Poisson, T.; Pannecoucke, X.; Charette, A. B.; Jubault, P. Angew. Chem. Int. Ed. 2017, 56, 13319.
For related studies on defluorinative alkylation of CF3 alkenes using silicates, see: Lang, S. B.; Wiles, R. J.; Kelly, C. B.; Molander, G. A. Angew. Chem. Int. Ed. 2017, 56, 15073.
For our preparation of 4CzIPN, please see: Engle, S. M.; Kirkner, T. R.; Kelly, C. B.* Org. Synth. 2019, 96, 455.
For related studies on defluorinative alkylation of CF3 alkenes using silicates, see: Lang, S. B.; Wiles, R. J.; Kelly, C. B.; Molander, G. A. Angew. Chem. Int. Ed. 2017, 56, 15073.