We acknowledge the EPSRC and GSK for financial support.
Uncovering the Importance of Proton Donors in TmI2-Promoted Electron Transfer: Facile CN Bond Cleavage in Unactivated Amides†
Article first published online: 12 JUN 2013
© 2013 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Angewandte Chemie International Edition
Volume 52, Issue 28, pages 7237–7241, July 8, 2013
How to Cite
Szostak, M., Spain, M. and Procter, D. J. (2013), Uncovering the Importance of Proton Donors in TmI2-Promoted Electron Transfer: Facile CN Bond Cleavage in Unactivated Amides. Angew. Chem. Int. Ed., 52: 7237–7241. doi: 10.1002/anie.201303178
- Issue published online: 4 JUL 2013
- Article first published online: 12 JUN 2013
- Manuscript Received: 16 APR 2013
- Funded Access
- 1The Amide Linkage: Structural Significance in Chemistry, Biochemistry and Materials Science, Wiley, Hoboken, 2000., , ,
- 2Selected examples:
- 2kModern Carbonyl Olefination, Wiley-VCH, Weinheim, 2004;,
- 6Organic Synthesis using Samarium Diiodide: A Practical Guide, RSC Publishing, Cambridge, 2010., , ,
- 7For reviews, see:
- 9aComprehensive Organic Synthesis, Pergamon, New York, 1991;, ,
- 9bReductions in Organic Chemistry, Ellis Horwood, Chichester, 1984;,
- 9cOrg. React. 1992, 42, 1., ,
- 10For reviews, see:
- 15Cleavage of a σ CO bond in ethers with lanthanides(II) has been reported:
- 15bSee, also Ref. , Ref.  and Ref. [12c].
- 16THEOCHEM 1982, 88, 217., , ,
- 20Catalytic use of TmI2 has already been demonstrated. See, Ref. [10b].
- 21Ester reduction with SmI2H2ONEt3 shows no chemoselectivity. See Ref. [14h].
- 22Complexes of nonclassical lanthanides(II) with alcohols have been reported: