Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 24, Pages 7564-7567Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b03488
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Funding
- 1000-Youth Talents Plan
- Jiangsu Specially-Appointed Professor Plan
- NSF of China [21402086]
- NSF of Jiangsu Province [BK20140594]
- U.S. NSF [CHE-1205646, CHE-1361104, OCI-1053575]
- Priority Academic Program Development of Jiangsu Higher Education Institutions
- Direct For Mathematical & Physical Scien [1361104] Funding Source: National Science Foundation
- Division Of Chemistry [1361104] Funding Source: National Science Foundation
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1205646] Funding Source: National Science Foundation
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A new strategy is reported for intramolecular Sp(3) C-H amination :under mild reaction conditions using iodoarene as catalyst and m-CPBA as oxidant. This C-H functionalization involving iodine(III) reagents generated in situ occurs readily at sterically hindered tertiary C-H bonds. DFT (M06-2X) calculations show that the preferred pathway involves an iodonium cation intermediate and proceeds via an energetically concerted transition state, through hydride transfer followed by the spontaneous C-N bond formation. ThiS leads to the experimentally observed amination at a chiral center without loss of stereo chemical information.
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