Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 5, Pages 1514-1517Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b13066
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Funding
- National Basic Research Program of China [2014CB910304]
- National Natural Science Foundation of China [21272260, 21472230]
- Thousand Talents Program Young Investigator Award
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The alkoxyl radical is an important reactive intermediate in mechanistic studies and organic synthesis; however, its current generation from alcohol oxidation heavily relies on transition metal activation under strong oxidative conditions. Here we report the first visible-light induced alcohol oxidation to generate alkoxyl radicals by cyclic iodine(III) reagent catalysis under mild reaction conditions. The beta-fragmentation of alkoxyl radicals enables selective C(sp(3))-C(sp(3)) bond cleavage and alkynylation/alkenylation reactions with various strained cycloalkanols, and for the first time with linear alcohols.
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