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Title: Metal-free amidation of ether sp3 C–H bonds with sulfonamides using PhI(OAc)2

Journal Article · · RSC Advances
DOI:https://doi.org/10.1039/C4RA09665G· OSTI ID:1607794
 [1];  [2];  [1];  [2]
  1. Yale Univ., New Haven, CT (United States)
  2. Univ. of Virginia, Charlottesville, VA (United States)
+ Show Author Affiliations

A selective protocol for the metal-free α-C–H amidation of ethers using sulfonamides and hypervalent iodine oxidants has been developed. The absence of precious metals and the conditions employed make the method environmentally attractive. A number of cyclic and acyclic, linear and branched ethers have been successfully amidated, and a broad sulfonamide scope has been demonstrated. Two unusual reactions, namely the amidation of an unactivated tert-butyl group and a tandem C–C coupling reaction, are further described here.

Research Organization:
Univ. of Virginia, Charlottesville, VA (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
Grant/Contract Number:
SC0001298
OSTI ID:
1607794
Journal Information:
RSC Advances, Vol. 4, Issue 89; ISSN 2046-2069
Publisher:
Royal Society of ChemistryCopyright Statement
Country of Publication:
United States
Language:
English
Citation Metrics:
Cited by: 22 works
Citation information provided by
Web of Science

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Direct Synthesis of Hemiaminal Ethers via a Three-Component Reaction of Aldehydes, Amines and Alcohols journal September 2015
Photochemical C−H Amination of Ethers and Geminal Difunctionalization Reactions in One Pot journal July 2019
Iodotriflamdation vs. Electrophilic Aromatic Iodination in the Reaction of N‐Phenyltriflamide with Alkenes journal June 2018
Copper-catalyzed oxidative intermolecular 1,2-alkylarylation of styrenes with ethers and indoles journal January 2018
Direct functionalization of alkyl ethers to construct hemiaminal ether skeletons (HESs) journal January 2018
Photochemical C−H Amination of Ethers and Geminal Difunctionalization Reactions in One Pot journal September 2019

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