In:
Angewandte Chemie International Edition, Wiley, Vol. 57, No. 29 ( 2018-07-16), p. 9078-9082
Abstract:
We herein report a robust catalyst‐free cross‐coupling between ArI(OAc) 2 and α‐stannyl nitriles, aided by TMSOTf. The transformation introduces a cyanoalkyl group to the ortho position of ArI(OAc) 2 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.
Type of Medium:
Online Resource
ISSN:
1433-7851
,
1521-3773
DOI:
10.1002/anie.201803455
Language:
English
Publisher:
Wiley
Publication Date:
2018
detail.hit.zdb_id:
2011836-3
detail.hit.zdb_id:
123227-7