News Release

May 31, 2022
N.E. CHEMCAT Awarded the Japan Petroleum Institute Award for Encouragement ofResearch and Development —“Development of NHC-Palladium Complex Catalyst and Immobilized
Complex Catalyst by Installation of Silyl Groups on Backbone Carbon”
In the "C-N cross-coupling reaction" used in the synthesis of organic electronic materials andpharmaceuticals, it contributes to reducing the amount of catalyst used and Pd elution andfacilitates the filtration process after the reaction.

N.E. CHEMCAT CORPORATION (Head office: Minato-ku, Tokyo; Representative Director & President
Matsuru Kushida) is pleased to announced that it was awarded “ the Japan Petroleum Institute Award for
Encouragement of Research and Development” for the Study on N-heterocyclic carbene (NHC)Palladium Complex Catalysts and Immobilized Complex Catalysts.
In this study, we synthesized a new N-heterocyclic carbene (NHC)-palladium complex catalyst bydirect installation of silyl groups on the backbone carbon of NHC ligands. Specifically, compared toexisting NHC-Pd complex catalysts, complex catalysts with dimethylallyl silyl installation improved
catalyst activities by up to 2.5 times*¹ in C-N cross-coupling reactions, which are used for thesynthesis of organic electronic materials and pharmaceuticals. In addition, this complex catalyst can besynthesized in just three steps using commercially available NHC compound as base. It was revealed
that the electronic properties of NHC ligands can be converted to electron-donating or electronwithdrawing by changing the substituents on the silicon atom in the silyl group.
In this study, we also successfully synthesized a immobilized complex catalyst by immobilizing theNHC-Pd complex catalyst on polystyrene resin. The common immobilization method, which uses thesubstituents attached to nitrogen as binding points, was not able to take full advantage of the bulkiness of
NHC ligands, which caused catalytic activities to decline. With this new immobilization method using thesilyl groups installed on the backbone carbon as the linking point for the support, the substituentsattached to nitrogen of the NHC can be utilized*¹ (Figure 1).

Figure 1. Catalyst design concept
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In addition, it was found that, by taking advantage of the improved electronic donating effect, the same levelof catalytic activities as NHC-Pd complex can be expressed in C-N cross-coupling reactions. We alsoachieved significant suppression of residual Pd (<1ppm) after C-N coupling reactions, thereby
demonstrating that this is a unique catalyst having the features of both complex catalyst andimmobilization catalyst*² (Figure 2).

Figure 2. Comparison of catalyst activities of complex immobilization catalysts(Conversion rate of complex immobilization catalyst (above); conversion rates of NHC-Pd
complex catalysts (below))
Results were highly appraised from academic and practical perspectives, which led us to win this award.
Going forward, by making these new catalysts available to the industrial sector, N.E. CHEMCAT willcontribute to reducing the use of catalysts with improved catalyst activities and simplifying refining processwith lower Pd leaching. We will pursue further R&D activities as the catalyst technology that we developed
through this study could be applied to catalyst reactions other than C-N cross-coupling reactions and leadto the development of complex immobilization catalysts using metals other than Pd. We are currently setting
up for mass production to release these catalysts, and aiming to expand our business even further.
*¹ Organometallics 2019, 38, 375−384. (DOI: 10.1021/acs.organomet.8b00757)*² Organometallics 2019, 38, 1872−1876. (DOI: 10.1021/acs.organomet.9b00159)*This research was conducted as joint research between N.E. CHEMCAT Corporation and research groups
led by Dr. Jun-Chul Choi, Dr. Norihisa Fukaya, Dr. Kazuhiro Matsumoto, et al. of Catalyst Design Center,
National Institute of Advanced Industrial Science and Technology,

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News Release⚫ The full explanation on the award can be found on the Japan Petroleum Institute website.
・The Japan Petroleum Institute website: https://www.sekiyu-gakkai.or.jp/jp/aword/2021/210601.html■ About N.E. CHEMCAT CORPORATION
N.E. CHEMCAT CORPORATION is engaged in the development, manufacturing, and distribution ofchemical catalysts, auto exhaust catalysts (including three-way catalysts and diesel auto catalysts), andfuel cell catalysts, and collection/refinement of precious metal catalysts.
27th floor, World Trade Center Bldg. South Tower, 2-4-1 Hamamatsucho, Minato-ku,
Tokyo 105-5127[Numazu Plant] 678 Ipponmatsu, Numazu City, Shizuoka Pref. 410-0314[Tsukuba Plant] 25-3 Kohshindaira, Bando City, Ibaraki Pref. 306-0608[Representative] Matsuru Kushida, Representative Director & President[Established]
April 1964
[Capital]
3,423.5 million yen[URL]
https://www.ne-chemcat.co.jp[Head Office]■Inquiries on this Release:
N.E. CHEMCAT CORPORATION (Public Relations)E-mail: info-pr@ne-chemcat.co.jp

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