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Visible-light-induced cross-coupling of aryl iodides with hydrazones via an EDA-complex.

ABSTRACT: A visible-light-induced, transition-metal and photosensitizer-free cross-coupling of aryl iodides with hydrazones was developed. In this strategy, hydrazones were used as alternatives to organometallic reagents, in the absence of a transition metal or an external photosensitizer, making this cross-coupling mild and green. The protocol was compatible with a variety of functionalities, including methyl, methoxy, trifluoromethyl, halogen, and heteroaromatic rings. Mechanistic investigations showed that the association of the hydrazone anion with aryl halides formed an electron donor-acceptor complex, which when excited with visible light generated an aryl radical via single-electron transfer.

SUBMITTER: Pan P

PROVIDER: S-EPMC9214885 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature

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Visible-light-induced cross-coupling of aryl iodides with hydrazones <i>via</i> an EDA-complex.

Pan Pan P Liu Shihan S Lan Yu Y Zeng Huiying H Li Chao-Jun CJ

Chemical science 20220523 24

A visible-light-induced, transition-metal and photosensitizer-free cross-coupling of aryl iodides with hydrazones was developed. In this strategy, hydrazones were used as alternatives to organometallic reagents, in the absence of a transition metal or an external photosensitizer, making this cross-coupling mild and green. The protocol was compatible with a variety of functionalities, including methyl, methoxy, trifluoromethyl, halogen, and heteroaromatic rings. Mechanistic investigations showed ...[more]

PMID: 35799801

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