jo6b01837_si_008.cif (20.58 kB)
Cobalt(II)-Catalyzed Aerobic Oxidation of Terminal-Capped Alkynyl α‑Cyano Alkanone Systems. An Oxygen-Mediated Radical Chain Reaction
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posted on 2016-10-17, 00:00 authored by Jing-Kai Huang, Ying-Chieh Wong, Tzu-Ting Kao, Chen-Tso Tseng, Kak-Shan ShiaA new N-hydroxyphthalimide
(NHPI)/Co(II)-catalyzed
protocol, mechanistically involving a sequence of α-hydrogen
abstraction, 5-exo-dig cyclization,
oxygen capture, hydrogen transfer, and 1,4-dehydration, has been developed
to facilitate aerobic oxidation of aryl-, silyl-, and alkyl-capped
alkynyl α-cyano alkanone systems to the corresponding highly
functionalized products in an effective manner, thus turning this
novel chain reaction, originally occurring spontaneously in low yields,
into a practical methodology.
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sequenceAerobicdehydrationmannerAlkynylNHPICyanomechanisticallyOxidationcyclization5- exomethodologyα- hydrogen abstractionhydrogen transferoxidationTerminal-Cappedsilylalkyl-capped alkynyl α- cyano alkanone systemsAlkanonenovel chain reactionCobaltfunctionalized productsyieldarylhydroxyphthalimideOxygen-Mediated Radical Chain Reaction
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