Challenging Catalytic C–H Bond Activation

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Abstract

Uwe Schneider
Edinburgh
Challenging Catalytic C–H Bond Activation Uwe Schneider The University of Edinburgh, EaStCHEM School of Chemistry The King’s Buildings, David Brewster Road, Edinburgh EH9 3FJ, UK [uwe.schneider@ed.ac.uk] Our laboratory has focused on the invention of novel catalysts and/or reactions. In this context, we have reported the first catalytic use of elemental gallium in organic synthesis,1 and allylic C(sp3)–H bond activation triggered by a sodium amide (Scheme–top).2 In this lecture, we disclose as well the challenging C–H bond activation of unprotected indoles and alkyl nitriles by copper(I)3 and carbon(0)4 catalyst systems, respectively (Scheme–bottom). R H ( M e 3 S i ) 2 N N a N H R ' P G R = A r , 3 - p y R ' = A r , H e t A r , t B u ; P G = P M P , P h g e n e r a t i o n o f n u c l e o p h i l i c a l l y l – N a v i a f o r m a l C ( s p 3 ) – H b o n d a c t i v a t i o n – t r a n s i t i o n m e t a l - f r e e – 2 7 e x a m p l e s – c o m p l e t e r e g i o s e l e c t i v i t y – E : Z = 1 9 : 1 ~ > 9 9 : 1 – 4 6 % e e p K a ~ 3 4 [ R = P h ] N H H H R N C p K a ~ 3 8 p K a ~ 3 5 C u I C 0 R References [1] Qin, B.; Schneider, U.* J. Am. Chem. Soc. 2016, 138, 13119–13122. [2] Bao, W.; Kossen, H.; Schneider, U.* J. Am. Chem. Soc. 2017, 139, 4362–4365. [3] Richards, J.; Schneider, U.* under review (Nat. Chem.). [4] Kossen, H.; Richards, J.; Bao, W.; Schneider, U.* under review (J. Am. Chem. Soc.). Uwe Schneider The University of Edinburgh EaStCHEM School of Chemistry The King’s Buildings David Brewster Road Edinburgh EH9 3FJ UK uwe.schneider@ed.ac.uk +44–131–650–4718 Uwe Schneider was born in Würzburg, Germany, and studied Chemistry in Germany and France. He received a PhD degree at IRCOF, France, with Professors Quirion and Pannecoucke [late 2003], before moving to the University of Tokyo, Japan, for postdoctoral research with Professor Kobayashi [early 2004]. He was an Assistant Professor at the University of Tokyo [2007–2011; tenure: 2009],1 before taking up a Lecturer position at the University of Edinburgh, UK [late 2011]. His research interests are focused on the development of sustainable organic synthesis including: exploitation of main group metals and non-metals in their unusual low-oxidation/valence states for base, acid, dual, ambiphilic, FLP, and/or transition metal-like redox catalysis;2 challenging C–H bond activation using metal–base and/or base catalysis;3 catalytic strong-bond activation in small molecules. Selected Papers: (1) Invited accounts: (a) Schneider, U.*; Huang, Y.-Y.; Chakrabarti, A.; Dao, H. T.; Morita, N.; Kobayashi, S.* Pure Appl. Chem. 2012, 84, 2417–2430; (b) Schneider, U.; Kobayashi, S.* Acc. Chem. Res. 2012, 45, 1331–1344. (2) (a) Qin, B.; Schneider, U.* J. Am. Chem. Soc. 2016, 138, 13119–13122; (b) Qin, B.; Richards, J.; Derelli, D.; Schneider, U.* submitted. (3) (a) Bao, W.; Kossen, H.; Schneider, U.* J. Am. Chem. Soc. 2017, 139, 4362–4365; (b) Richards, J.; Schneider, U.* under review (Nat. Chem.); (c) Kossen, H.; Richards, J.; Bao, W.; Schneider, U.* under review (J. Am. Chem. Soc.). Download PDF

  • Venue

    Theatre C, Purdie, University of St. Andrews, St. Andrews, Fife, Scotland, UK

  • Venue Info

  • Date

    May 23, 2018

  • Time

    From: 15h30 To: 16h30

  • Sponsor

    University of St Andrews
    The oldest university in Scotland, with international renown for both research and education of undergraduates and postgraduates.

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