2022
DOI: 10.1039/d2nj01186g
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Unexpected ester and phosphonate radical generation by hypervalent iodine compounds for synthesizing 6-phenanthridine derivatives

Abstract: An unprecedented elimination of diazomethane process of diazo group bearing hypervalent iodine reagent has been described. The process provides ester and phosphonate radicals, which can react with 2-isocyanobiaryls to afford...

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Cited by 6 publications
(3 citation statements)
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“…28 Reaction of this open shell species with 38 followed by radical addition to the neighbouring phenyl ring, oxidation, and deprotonation, leads to the formation of 39 (Scheme 10). 29 Also making use of the mesolitic C-I bond cleavage after one electron reduction, Li and co-workers recently reported a photoredox catalysed cascade transformation that delivers substituted acridines by reaction of 4 with diarylamine substrates 41. The authors propose the initial generation of the diazomethyl radical intermediate (int-VI) from 4 and subsequent interception of this species by 41 to generate the radical adduct (int-IX).…”
Section: Transfer Of the Diazo Group Via Radical Processesmentioning
confidence: 99%
See 1 more Smart Citation
“…28 Reaction of this open shell species with 38 followed by radical addition to the neighbouring phenyl ring, oxidation, and deprotonation, leads to the formation of 39 (Scheme 10). 29 Also making use of the mesolitic C-I bond cleavage after one electron reduction, Li and co-workers recently reported a photoredox catalysed cascade transformation that delivers substituted acridines by reaction of 4 with diarylamine substrates 41. The authors propose the initial generation of the diazomethyl radical intermediate (int-VI) from 4 and subsequent interception of this species by 41 to generate the radical adduct (int-IX).…”
Section: Transfer Of the Diazo Group Via Radical Processesmentioning
confidence: 99%
“… 28 Reaction of this open shell species with 38 followed by radical addition to the neighbouring phenyl ring, oxidation, and deprotonation, leads to the formation of 39 ( Scheme 10 ). 29 …”
Section: Reactivity Of α-Diazo-λ 3 -Iodanesmentioning
confidence: 99%
“…In 2022, Sun, Wang and co‐workers developed a reaction system for the formation of C(sp 2 )−C bonds promoted by ester radical A , which was used for the synthesis of 6‐phenanthridine derivatives 21 (Scheme 8). [47] The ester radical A in this reaction system was unexpectedly generated by diazomethyl‐substituted iodine(III) compound 3 i and captured by 2‐isocyanobiaryl 20 to generate imine radical B , which can be directly converted into product 21 .…”
Section: Ester Radicals Generationmentioning
confidence: 91%