Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 18, Pages 9264-9271Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01695
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Funding
- MEXT [24245005, 15H00938, 15H02158]
- Fukui Institute for Fundamental Chemistry (FIFC)
- Grants-in-Aid for Scientific Research [15H02158, 15H00938, 26220803] Funding Source: KAKEN
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The mechanism of the C-H activation of aldehydes and the succeeding acylation of an alkene using a hypervalent iodine reagent is investigated by theoretical calculations. In contrast to the initial proposed mechanism, the present calculations show that the hypervalent iodine is the initiator of the radical reaction. The formation of acyl radical is rate-determining, and the resulting radical acts as the chain carrier. The kinetic isotope effect (KIE) of deuterated aldehyde, as well as other experimental observations, can now be rationalized from the newly proposed mechanism.
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