Date/Time/ Venue Title/Speaker 26 Jan (Wed) 4pm – 5pm @ S8 Level 3 Executive Classroom Catalytic Reactions Involving Activation Catalytic Reactions Involving Activation of Unreactive Bonds of Unreactive Bonds Professor Naoto Chatani Osaka University , Japan Host : Asst Prof Martin J Lear About the Speaker All are Welcome 1991 and The fourth Green and Sustainable Chemistry Award: Minister of Education, Sports, Culture, Science and Technology Prize in 2005. His current research interests center on the area of catalysis. Professor Naoto Chatani studied chemistry at Osaka University and received his Ph. D. in 1984 under the guidance by Professors Noboru Sonoda and Shinji Murai. In 1984 he joined the Institute of Scientific and Industrial Research at Osaka University and worked in the laboratory of Prof. Terukiyo Hanafusa. After postdoctoral studies (1988-1989 under Prof. Scott E. Denmark, the University of Illinois, Urbana-Champaign), he moved back to Osaka University and worked with Prof. Shinji Murai as Assistant Professor. He was promoted to Associate Professor in 1992 and Professor in 2003. He received Young Chemist Award of the Chemical Society of Japan in Abstract N H O N N O O N H 77% 5 m ol% Ru 3 (CO ) 12 H 2 O (2 equiv) ethylene (7 atm ) toluene,160 °C ,24 h + C O 10 atm We found new types of some catalytic reactions involving the cleavage of C-CN bonds in nitriles, which proceed via a silicon-assisted mechanism. [2] Silylation, [3] reductive decyanation, [4] intramolecular C-C bond formation, [5] and the Mizoroki-Heck type reaction [6] will be discussed. We reported some results for a series of Ru- and Rh-catalyzed carbonylation reactions of C-H bonds. In all cases, the substrates required the presence of an sp 2 nitrogen. This suggests that the coordination of the sp 2 nitrogen to the catalyst is an important for the reaction to proceed. Our findings also showed that, in such carbonylation reactions of C-H bonds, both high CO pressures and high reaction temperatures were required for a successful reaction. Because of this, carbonyl compounds, such as ketones, esters, and amides are not typically used in the Ru- and Rh-catalyzed C-H bond carbonylation because of their low coordination ability. The substrates must compete with the higher pressure of CO. This encouraged us to develop a new bidentate system that would be applicable to the ortho C-H bond carbonylation of aromatic amides. [1] Department of Chemist Seminar Announcement R C N Rh Si R Rh CN Si N C Rh R Si R Si R H R SiEt 3 R Ar Si Si H Si SiEt 3 [1] Inoue, S.; Shiota, H.; Fukumoto, Y. Chatani, N. J. Am. Chem. Soc. 2009, 131, 6898. [2] Taw, F. L.; Mueller, A. H.; Bergman, R. G.; Brookhart, M. J. Am. Chem. Soc. 2003, 125, 9808. [3] Tobisu, M.; Kita, Y.; Chatani, N. J. Am. Chem. Soc. 2006, 128, 8152. [4] Tobisu, M.; Nakamura, R.; Kita, Y.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 3174. [5] Tobisu, M.; Kita,Y.; Ano, Y.; Chatani, N. J. Am. Chem. Soc. 2008, 130, 15982. [6] Kita, Y.; Tobisu, M. ; Chatani, N. Org. Lett. 2010, 12, 1864.

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Date/Time/Venue Title/Speaker

26 Jan (Wed)4pm – 5pm

@ S8 Level 3 Executive Classroom

Catalytic Reactions Involving Catalytic Reactions Involving Activation of Unreactive BondsActivation of Unreactive Bonds

Professor Naoto ChataniOsaka University , JapanHost : Asst Prof Martin J Lear

About the Speaker

All are Welcome

1991 and The fourth Green and Sustainable Chemistry Award: Minister of Education, Sports, Culture, Science and Technology Prize in 2005. His current research interests center on the area of catalysis.

Professor Naoto Chatani studied chemistry at Osaka University and received his Ph. D. in 1984 under the guidance by Professors Noboru Sonoda and Shinji Murai. In 1984 he joined the Institute of Scientific and Industrial Research at Osaka University and worked in the laboratory of Prof. Terukiyo Hanafusa. After postdoctoral studies (1988-1989 under Prof. Scott E. Denmark, the University of Illinois, Urbana-Champaign), he moved back to Osaka University and worked with Prof. Shinji Murai as Assistant Professor. He was promoted to Associate Professor in 1992 and Professor in 2003. He received Young Chemist Award of the Chemical Society of Japan in

Abstract

77%

5 mol% Ru3(CO)12H2O (2 equiv)ethylene (7 atm)

toluene, 160 °C, 24 h+ CO

10 atm

We found new types of some catalytic reactions involving the cleavage of C-CN bonds in nitriles, which proceed via a silicon-assisted mechanism.[2] Silylation,[3] reductive decyanation,[4] intramolecular C-C bond formation,[5] and the Mizoroki-Heck type reaction[6] will be discussed.

We reported some results for a series of Ru- and Rh-catalyzed carbonylation reactions of C-H bonds. In all cases, the substrates required the presence of an sp2 nitrogen. This suggests that the coordination of the sp2 nitrogen to the catalyst is an important for the reaction to proceed. Our findings also showed that, in such carbonylation reactions of C-H bonds, both high CO pressures and high reaction temperatures were required for a successful reaction. Because of this, carbonyl compounds, such as ketones, esters, and amides are not typically used in the Ru- and Rh-catalyzed C-H bond carbonylation because of their low coordination ability. The substrates must compete with the higher pressure of CO. This encouraged us to develop a new bidentate system that would be applicable to the ortho C-H bond carbonylation of aromatic amides.[1]

Department of Chemistry

Seminar Announcement

R C NRh Si R

RhCNSiNC

R Si

R Si R H RSiEt3

R Ar

Si Si H Si SiEt3

[1] Inoue, S.; Shiota, H.; Fukumoto, Y. Chatani, N. J. Am. Chem. Soc. 2009, 131, 6898. [2] Taw, F. L.; Mueller, A. H.; Bergman, R. G.; Brookhart, M. J. Am. Chem. Soc. 2003, 125, 9808. [3] Tobisu, M.; Kita, Y.; Chatani, N. J. Am. Chem. Soc. 2006, 128, 8152.[4] Tobisu, M.; Nakamura, R.; Kita, Y.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 3174.[5] Tobisu, M.; Kita,Y.; Ano, Y.; Chatani, N. J. Am. Chem. Soc. 2008, 130, 15982. [6] Kita, Y.; Tobisu, M. ; Chatani, N. Org. Lett. 2010, 12, 1864.