Department of Chemistry
Indian Institute of Technology Delhi

Chiral Acid-Enabled Achiral Rh(III) & Co(III)-Catalyzed Asymmetric C-H Bond Functionalization

Prof. Shigeki Matsunaga

Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan


Date: Dec 10th 2018 (Monday)
Time: 4:00 PM
Venue: Committee Room, Chemistry Department, 6th Floor

Our group is interested in the development of atom- and step-economical catalytic transformation. Towards this goal, we reported the utility of a cationic high valent Cp*Co(III) catalysis for C-H activation in 2013.1 To further expand the utility of achiral Cp*M(III) (M = Co, Rh, Ir) catalysts in enantioselective C-H bond functionalization, we recently developed chiral acids/achiral CpxRh(III)/Co(III) hybrid catalysts. Cp*Rh(III) in combination with chiral sulfonates enabled asymmetric induction after C-H activation,2,3 while Cp*Rh(III) with a chiral carboxylic acid enabled asymmetric induction at C-H activation step.4 CpxCo(III) with a chiral carboxylic acid system for asymmetric C(sp3)-H bond functionalization will also be introduced.5

  1. (a) Yoshino, T.; Ikemoto, H.; Matsunaga, S.; Kanai, M. Angew. Chem. Int. Ed. 2013, 52, 2207; (b) Review: Yoshino, T.; Matsunaga, S. Adv. Synth. Catal. 2017, 359, 1245; For recent examples, see: (c) Ikemoto. H.; Tanaka, R.; Sakata, K.; Kanai, M.; Yoshino, T.; Matsunaga, S. Angew. Chem. Int. Ed. 2017, 56 7156; (d) Kawai, K.; Bunno, Y.; Yoshino, T.; Matsunaga, S. Chem. Eur. J. 2018, 24, 10231.
  2. Satake, S.; Kurihara, T.; Nishikawa, K.; Mochizuki, T.; Hatano, M.; Ishihara, K.; Yoshino, T.; Matsunaga, S. Nature Catalysis 2018, 1, 585.
  3. Spiro-chiral sulfonate: Kurihara, T.; Satake, S.; Hatano, M.; Ishihara K.; Yoshino T.; Matsunaga, S. Chem. Asian. J. 2018, 13, 2378.
  4. Lin, L.; Fukagawa, S.; Sekine, D.; Tomita, E.; Yoshino, T.; Matsunaga, S. Angew. Chem. Int. Ed. 2018, 57, 12048.
  5. Fukagawa, S.; Kato, Y.; Tanaka, R.; Kojima, M.; Yoshino, T.; Matsunaga, S. Angew. Chem. Int. Ed. in press [DOI: 10.1002/anie.201812215].

  6. About the speaker: Shigeki Matsunaga was born in Kyoto (1975). He received his Bachelor degree in 1998 from the University of Tokyo, where he continued his PhD work under the supervision of Professor Masakatsu Shibasaki and completed the work in 2003. He took up an assistant professor position in Prof. Shibasaki’s group at the University of Tokyo in 2001, and was promoted there to a senior lecturer in 2008. He joined Prof. Motomu Kanai’s group at the University of Tokyo in 2010, and promoted to an associate professor in 2011. In 2015, we moved to Hokkaido University as a full professor and launched his group there. He is the recipient of the Chemical Society of Japan Award for Young Chemists (2006), Thieme Journal Award (2008), Mitsui Chemicals Catalysis Science Award of Encouragement (2009), Inoue Research Science Award (2010), Merck-Banyu Lectureship Award 2010, Asian-Core-Program Lectureship Awards 2015 (Korea & Thailand) and 2018 (China & Singapore), 4th Thomson Reuters Research Front Award (2016) and others. His research interests are in the development of cooperative bimetallic asymmetric catalysts, C-H activation catalysts, and their application to the synthesis of biologically active compounds.

    All are cordially invited to attend.
    Convener (Seminars)