Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 1, Pages 296-299Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201710322
Keywords
chlorination; directing groups; halogenation; hydrogen transfer; radical reactions
Categories
Funding
- American Chemical Society Petroleum Research Fund Doctoral New Investigator Program (PRF) [54824-DNI1]
- Duke University
- National Institute of General Medical Sciences [T32GM007105-41]
- Burroughs Wellcome Fellowship
- NSF predoctoral fellowship [NSF DGF 1106401]
- NSF [CHE-0923097]
- NSF
- NIH, HHMI
- North Carolina Biotechnology Center
- Duke (Duke Magnetic Resonance Spectroscopy Center)
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Masked alcohols are particularly appealing as directing groups because of the ubiquity of hydroxy groups in organic small molecules. Herein, we disclose a general strategy for aliphatic gamma-C(sp(3))-H functionalization guided by a masked alcohol. Specifically, we determine that sulfamate ester derived nitrogen-centered radicals mediate 1,6-hydrogen-atom transfer (HAT) processes to guide gamma-C(sp(3))-H chlorination. This reaction proceeds through a light-initiated radical chain-propagation process and is capable of installing chlorine atoms at primary, secondary, and tertiary centers.
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