Photoinduced difunctionalization with bifunctional reagents containing N-heteroaryl moieties

Lee, Wooseok; Park, Inyoung; Hong, Sungwoo

doi:10.1007/s11426-023-1589-7

Cited by 26 publications

(7 citation statements)

References 83 publications

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“…22 The residue was purified by column chromatography on silica gel with ethyl acetate to afford 5a (17 mg, 70% yield) as a yellow oil; 1 H NMR (500 MHz, CDCl 3 ) δ 7.40−7.32 (m, 4H), 7.29−7.23 (m, 1H), 4.14 (q, J = 6.6 Hz, 1H), 1.72 (s, 2H), 1.42 (d, J = 6.6 Hz, 3H); 13 C{ 1 H} NMR (125 MHz, CDCl 3 ) δ 147. 4,128.6,127.0,125.9,51.5,. 22 The residue was purified by column chromatography on silica gel with ethyl acetate to afford 5b (27 mg, 69% yield) as a yellow oil; 1 H NMR (400 MHz, CDCl 3 ) δ 7.41 (d,J = 8.4 Hz,2H),7.20 (d,J = 8.4 Hz,2H), 4.06 (q, J = 6.6 Hz, 1H), 1.56 (s, 2H), 1.32 (d, J = 6.6 Hz, 3H); 13 C{ 1 H} NMR (100 MHz, CDCl 3 ) δ 146.7, 131.…”

Section: -(((4-(1-methoxymentioning

confidence: 99%

Electrochemical Benzylic C–H Amination via N-Aminopyridinium

Liu,

Du,

Zhang

et al. 2024

J. Org. Chem.

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An electrochemical protocol for benzylic C(sp 3 )−H aminopyridylation via direct C−H/N−H cross-coupling of alkylarenes with N-aminopyridinium triflate has been developed. This method features excellent site-selectivity, broad substrate scope, redox reagent-free and facile scalability. The generated benzylaminopyridiniums can be readily converted to benzylamines via electroreductive N−N bond cleavage.

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Section: -(((4-(1-methoxymentioning

confidence: 99%

Electrochemical Benzylic C–H Amination via N-Aminopyridinium

Liu,

Du,

Zhang

et al. 2024

J. Org. Chem.

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“…There is a recent stand-alone report of a 1,2,5-trifunctionalization across two alkenes; however, this is a special case with a 1,2-boron shift within an allylic boronic species, which stands of course as a prerequisite . While it is established that bifunctional reagents containing a photolabile N–X bond form chemically distinct entities that stay intact during the addition across an olefin, we desired for an exception. We postulated an in situ conversion of the transient radical B to a more stable radical C prior to the addition to olefin (Figure C).…”

Section: Introductionmentioning

confidence: 99%

γ-Amino Alcohols via Energy Transfer Enabled Brook Rearrangement

Laskar,

Dutta,

Spies

et al. 2024

J. Am. Chem. Soc.

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In the long-standing quest to synthesize fundamental building blocks with key functional group motifs, photochemistry in the recent past has comprehensively established its attractiveness. Amino alcohols are not only functionally diverse but are ubiquitous in the biologically active realm of compounds. We developed bench-stable bifunctional reagents that could then access the sparsely reported γ-amino alcohols directly from feedstock alkenes through energy transfer (EnT) photocatalysis. A designed 1,3-linkage across alkenes is made possible by the intervention of a radical Brook rearrangement that takes place downstream to the EnT-mediated homolysis of our reagent(s). A combination of experimental mechanistic investigations and detailed computational studies (DFT) indicates a radical chain propagated reaction pathway.

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“…Olefins as unsaturated hydrocarbons are remarkably valuable synthetic scaffolds in organic synthetic chemistry. 8 Excited olefins allow for many chemical transformations such as atom transfer reactions, 9 [2 + 2] cyclizations, 10 and E → Z isomerizations 11 that cannot be realized in the ground state. Nevertheless, the direct excitation of most olefinic compounds via visible light irradiation is disfavored, basically due to the comparatively low absorption at longer wavelengths.…”

Section: Introductionmentioning

confidence: 99%