Merck Seminar in the Chemical Sciences: Development of Direct C-H Amination Reactions

Seminar: Organic Chemistry | November 14 | 11 a.m.-12 p.m. | 120 Latimer Hall

 Prof. Sukbok Chang, KAIST

 College of Chemistry

Aryl amines are a key synthetic unit widely utilized in organic synthesis, coordination chemistry, materials science and pharmaceutical industry. Current preparative routes to those compounds require either prefunctionalized starting materials or conditions needing external oxidants, thus inevitably generating stoichiometric amounts of side wastes. We have developed a series of direct C-H amidation and amination reactions of low-reacting -hydrocarbons by using organic azides as the amino source releasing molecular nitrogen as the single by-product. More recenly, 1,4,2-dioxazol-5-ones and their functional derivatives have also been proved as the highly efficient and robust amino sources in this direct C-H amination. The reaction is catalyzed by a cationic rhodium, iridium, or cobalt complex under external oxidant-free conditions, and a broad range of chelate group-containing arenes are selectively amidated with excellent functional group tolerance, thereby opening a new avenue to environmentally benign C-N bond formation which can be immediately applied in synthetic chemistry, medicinal, and materials science.

[1] J. Y. Kim, S. H. Park, J. Ryu, S. H. Cho, S. H. Kim, S. Chang, J. Am. Chem. Soc. 2012, 134, 9110-9113
[2] J. Ryu, J. Kwak, K. Shin, D. Lee, S. Chang, J. Am. Chem. Soc. 2013, 135, 12861-12868
[3] S. H. Park, Y. Park, S. Chang, Organic Syntheses 2014, 91, 52-59
[4] S. H. Park, J. Kwak, K. Shin, J. Ryu, Y. Park, S. Chang, J. Am. Chem. Soc. 2014, 136, 2492-2502.
[5] Y. Park, K. T. Park, J. G. Kim, S. Chang, J. Am. Chem. Soc. 2015, 137, 4534–4542
[6] Y. Park, J. Heo, M.-H. Baik, S. Chang, J. Am. Chem. Soc. 2016, 138, 14020-14029
[7] Y. Park, Y. Kim, S. Chang, Chem. Rev. 2017, 117, 9247–9301
[8] H. Kim, S. Chang, Acc. Chem. Res. 2017, 50, 482–486

 Light refreshments will be served at 10:50 at The Coffee Lab, 510-643-0572