2022
DOI: 10.1021/acs.joc.2c01703
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Intermolecular C–H Aminocyanation of Indoles via Copper–iodine Cocatalyzed Tandem C–N/C–C Bond Formation

Abstract: An efficient copper–iodine cocatalyzed intermolecular C–H aminocyanation of indoles with a broad substrate scope has been developed for the first time. This method enables highly step-economic access to 2-amino-3-cyanoindoles in moderate to good yields and provides a complementary strategy for the regioselective difunctionalization of carboncarbon double bonds of interest in organic synthesis and related areas. Mechanistic studies suggest that these transformations are initiated by iodine-mediated C2–H aminat… Show more

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Cited by 15 publications
(2 citation statements)
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“…[ 37,38 ] Therefore, the chemical compositions of these membrane surfaces are listed in Table 2, where N elements increased gradually with the PPTA content increasing in the substrates, while the O/N ratio decreased from 1.66 to 1.38, indicating a gradual increase in crosslinking density. [ 39–41 ] This trend might be advantageous to maintain the excellent salt rejection, and the reason for this phenomenon maybe mainly explained that more mPD stored on the substrate surface diffused to react with TMC because of the strong affinity between the mPD and PPTA exposed on the substrate. However, higher crosslinking density of the polyamide functional layer meant higher rejection and lower permeation because the main filtration resistance came from the polyamide layer.…”
Section: Resultsmentioning
confidence: 99%
“…[ 37,38 ] Therefore, the chemical compositions of these membrane surfaces are listed in Table 2, where N elements increased gradually with the PPTA content increasing in the substrates, while the O/N ratio decreased from 1.66 to 1.38, indicating a gradual increase in crosslinking density. [ 39–41 ] This trend might be advantageous to maintain the excellent salt rejection, and the reason for this phenomenon maybe mainly explained that more mPD stored on the substrate surface diffused to react with TMC because of the strong affinity between the mPD and PPTA exposed on the substrate. However, higher crosslinking density of the polyamide functional layer meant higher rejection and lower permeation because the main filtration resistance came from the polyamide layer.…”
Section: Resultsmentioning
confidence: 99%
“…As part of our continuous efforts to develop innovative methods for the synthesis and functionalization of indoles, [ 11 ] we present our unexpected findings on a one‐step, three‐component intermolecular C—H diamination reaction for the highly regioselective synthesis of 2,3‐diaminoindole. This reaction utilizes a copper‐iodine co‐catalytic system (Scheme 1b).…”
Section: Background and Originality Contentmentioning
confidence: 99%