Journal
CHEMICAL SCIENCE
Volume 9, Issue 19, Pages 4500-4504Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8sc01214h
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Funding
- Ohio State University, National Institutes of Health [NIH R35 GM119812]
- National Science Foundation [NSF CAREER 1654656]
- American Chemical Society Petroleum Research Fund
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A radical relay strategy for mono-and di-halogenation (iodination, bromination, and chlorination) of sp3 C-H bonds has been developed. This first example of b C-H di-halogenation is achieved through sequential C-H abstraction by iterative, hydrogen atom transfer (HAT). A double C-H functionalization is enabled by in situ generated imidate radicals, which facilitate selective Nc to Cc radical translocation and tunable C-X termination. The versatile, geminal di-iodide products are further elaborated to b ketones and vinyl iodides. Mechanistic experiments explain the unique di-functionalization selectivity of this iterative HAT pathway, wherein the second C-H iodination is twice as fast as the first.
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