2022
DOI: 10.1039/d1cc07143b
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A radical–radical cross-coupling reaction of xanthene with sulfonyl hydrazides: facile access to xanthen-9-sulfone derivatives

Abstract: A straightforward strategy for direct incorporation of sulfonyl units into xanthene moiety for accessing xanthen-9-sulfone derivatives in good to excellent yields has been established via metal-free radical-radical cross-coupling reaction of...

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Cited by 18 publications
(13 citation statements)
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“…DHA is known to act as a radical inhibitor. 18 Although this transformation should involve a radical process (see the discussion below), the cross-coupling of aryl fluorides 1 with 2h proceeded very well under the standard conditions, giving the desired cross-coupling products in good yields ( 3ah : 76%; 3jh : 71%; 3kh : 75%; 3lh : 45%; 3nh : 71%). Similarly, 9 H -xanthene ( 2i ) also produced good results with aryl fluorides 1 under the same conditions ( 3ai : 77%; 3ji : 85%; 3ki : 80%; 3ni : 74%; 3pi : 74%).…”
Section: Resultsmentioning
confidence: 99%
“…DHA is known to act as a radical inhibitor. 18 Although this transformation should involve a radical process (see the discussion below), the cross-coupling of aryl fluorides 1 with 2h proceeded very well under the standard conditions, giving the desired cross-coupling products in good yields ( 3ah : 76%; 3jh : 71%; 3kh : 75%; 3lh : 45%; 3nh : 71%). Similarly, 9 H -xanthene ( 2i ) also produced good results with aryl fluorides 1 under the same conditions ( 3ai : 77%; 3ji : 85%; 3ki : 80%; 3ni : 74%; 3pi : 74%).…”
Section: Resultsmentioning
confidence: 99%
“…The radical (117) also could be gained from the sulfonyl iodide (115) via a sulfonyl anion intermediate (116). Then the radical (117) reacted with an alkene and gave a radical intermediate (119) which was then oxidized and produced a carbon cation species (120). The cation (120) might react with I − to give an iodide compound, which proceeded with the elimination of HI or loss of the H + to produce vinyl sulfones.…”
Section: Sulfonylation Of Alkenes and Alkynesmentioning
confidence: 99%
“…Due to their unique structure, xanthenes and their derivatives were widely used in chemical research, and recently, they were involved in some C–H activation studies, , especially several electrochemical examples, and an electrochemical sulfonylaztion of xanthenes ( 284 ) at the C-9 position using sulfonyl hydrazides as sulfonating reagent was developed by Mo and co-workers in 2022 (Scheme ). This oxidative C­(sp 3 )-H activation was realized by charging a carbon rod anode and a platinum plate cathode under a constant current of 15 mA, using n Bu 4 NI as an electrolyte, as well as a mediator.…”
Section: Sulfonylation Of Heterocyclic Compoundsmentioning
confidence: 99%
“…In fact, such an in situ-formed π-palladium allyl species can be attacked by sulfonyl sources acting as nucleophiles to produce the corresponding N -allyl sulfonamides. The most common previously reported sulfonyl sources include sulfonyl hydrazide and sulfinic acid sodium salt . Herein, the palladium-catalyzed, three-component tandem reaction of N -buta-2,3-dienyl sulfonamides ( 1 ) with iodides ( 2 ) and various sulfonyl sources ( 3 ) for the rapid, efficient, and selective synthesis of functionalized N -allyl sulfonamides in moderate to good yields and with high ( Z )-isomer stereoselectivity is reported (Scheme , eq 6).…”
Section: Introductionmentioning
confidence: 99%