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- Publisher
- Wiley
- Copyright
- © 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
- ISSN
- 2193-5807
- eISSN
- 2193-5815
- DOI
- 10.1002/ajoc.201900128
- Publisher site
- See Article on Publisher Site
Abstract
In the present study, a facile, efficient, and environmentally benign approach for secondary amide transamidation by using tert‐butyl hydroperoxide (TBHP) as a radical initiator has been developed. The method involves a two‐step approach in which the first step is the C−N bond activation via N‐functionalization with Boc to weaken the amide C−N bond by making amide non‐planar and electronically destabilized. In the second step, an N‐Boc‐activated secondary amides undergoes transamidation with the various primary, secondary, aliphatic, aromatic, as well as the sterically hindered amines, using TBHP as a radical initiator to give the products in good to excellent yields. TBHP is easily available, inexpensive, and an environmentally friendly radical initiator. A broad substrate scope with extensive functional group tolerance, metal and catalyst‐free approach, and operational simplicity are the important characteristics of the present protocol.
Journal
Asian Journal of Organic Chemistry – Wiley
Published: Jun 1, 2019
Keywords: ; ; ; ;