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Selective ortho C−H Cyanoalkylation of (Diacetoxyiodo)arenes through [3,3]‐Sigmatropic Rearrangement.
- Source :
- Angewandte Chemie; 7/16/2018, Vol. 130 Issue 29, p9216-9220, 5p
- Publication Year :
- 2018
-
Abstract
- Abstract: We herein report a robust catalyst‐free cross‐coupling between ArI(OAc)<subscript>2</subscript> and α‐stannyl nitriles, aided by TMSOTf. The transformation introduces a cyanoalkyl group to the ortho position of ArI(OAc)<subscript>2</subscript> and simultaneously reduces the aryl iodine(III) to iodide, thus providing α‐(2‐iodoaryl) nitrile as the product. This transformation could be completed within 5 min at −78 °C and features superb functional‐group tolerance and efficient scalability. DFT calculations indicate that the formation of a ketenimine(aryl)iodonium intermediate and subsequent [3,3]‐sigmatropic rearrangement are involved as key steps. [ABSTRACT FROM AUTHOR]
- Subjects :
- SIGMATROPIC rearrangements
NITRILES
SCALABILITY
IODINE
IODIDES
ARYL iodides
TOLERATION
Subjects
Details
- Language :
- English
- ISSN :
- 00448249
- Volume :
- 130
- Issue :
- 29
- Database :
- Complementary Index
- Journal :
- Angewandte Chemie
- Publication Type :
- Academic Journal
- Accession number :
- 130647100
- Full Text :
- https://doi.org/10.1002/ange.201803455