R.A.F. and D.W.C.M. are grateful to the National Institutes of Health (1R15M075960-01 and R01-GM093213-01) for support of this work.
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Communication
Mechanistic Complexity in Organo–SOMO Activation†
Article first published online: 14 JUL 2010
DOI: 10.1002/anie.201001673
Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Devery, James J., Conrad, Jay C., MacMillan, David W. C. and Flowers, Robert A. (2010), Mechanistic Complexity in Organo–SOMO Activation. Angew. Chem. Int. Ed., 49: 6106–6110. doi: 10.1002/anie.201001673
- †
Publication History
- Issue published online: 12 AUG 2010
- Article first published online: 14 JUL 2010
- Manuscript Received: 19 MAR 2010
Funded by
- National Institutes of Health. Grant Numbers: 1R15M075960-01, R01-GM093213-01
Keywords:
- ceric ammonium nitrate;
- organocatalysis;
- phase transfer;
- reaction mechanisms;
- single electron transfer
Wet chemistry: Organo-SOMO activation is an intricate process. The catalyst is deactivated in the absence of H2O and its concentration is maintained with 2 equivalents of H2O. The kinetic role of ceric ammonium nitrate (CAN) is masked by phase transfer and its limited solubility is enhanced by added H2O. Mechanistic studies show that careful addition of H2O to dried reagents greatly enhances reaction. TMS=trimethylsilyl.