2022
DOI: 10.1021/acs.orglett.2c02557
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Visible-Light-Induced Dual C(sp3)–H Bond Functionalization of Tertiary Amine via Hydrogen Transfer to Carbene and Subsequent Cycloaddition

Abstract: Herein, we describe the dual C­(sp3)–H bond functionalization of a tertiary amine through hydride-transfer-induced dehydrogenation, followed by cycloaddition, using an easily preparable diazoester as a new type hydride-acceptor precursor under mild, redox-neutral conditions. With carbene as a hydrogen acceptor, this method was demonstrated by the preparation of a broad range of functionalized isoxazoldines in moderate to good yields.

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Cited by 12 publications
(7 citation statements)
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“…A possible reason is that there are no required competent cycloaddition acceptors and sufficient amounts of the transient acyclic enamine intermediates . To the best of our knowledge, the only example of that was revealed by Jin, wherein a visible-light-induced 1,3-dipolar cycloaddition of triethylamine with N -hydroximoyl chlorides fabricated isooxazoline derivatives (Scheme c) . In this context, we believe that triethylamine can act as an additional and exquisite type of ethylene source in the traditional [4 + 2] cycloaddition to directly arrive at 3,4-nonsubstituted 2-arylquinoline derivatives.…”
mentioning
confidence: 89%
“…A possible reason is that there are no required competent cycloaddition acceptors and sufficient amounts of the transient acyclic enamine intermediates . To the best of our knowledge, the only example of that was revealed by Jin, wherein a visible-light-induced 1,3-dipolar cycloaddition of triethylamine with N -hydroximoyl chlorides fabricated isooxazoline derivatives (Scheme c) . In this context, we believe that triethylamine can act as an additional and exquisite type of ethylene source in the traditional [4 + 2] cycloaddition to directly arrive at 3,4-nonsubstituted 2-arylquinoline derivatives.…”
mentioning
confidence: 89%
“…In 2022, Jin et al 36 presented a metal-free method for the dual functionalization of C(sp 3 )–H bonds in tertiary amines, which involved the use of a diazoester as a hydride-acceptor precursor. The process involved hydride-transfer-induced dehydrogenation followed by cycloaddition and was carried out under mild, redox-neutral and photo-mediated conditions.…”
Section: Carbene Intermediate-assisted Reactionmentioning
confidence: 99%
“…In 2022, Jin et al 36 presented a metal-free method for the dual functionalization of C(sp 3 )-H bonds in tertiary amines, which involved the use of a diazoester as a hydride-acceptor precursor.…”
Section: Carbene Intermediate-assisted Reactionmentioning
confidence: 99%
“…Very recently, the Jin group reported a visible‐light‐induced, carbene‐mediated cycloaddition of tertiary amines with concurrent functionalization of both amine α ‐ and β ‐C−H bonds (Scheme 33). [66] A broad scope of dipoles readily react with both acyclic and cyclic tertiary amines to give various heterocyclic products in moderate to good yields. For instance, a reaction employing N ‐methylpiperidine and N ‐hydroximoyl chloride 99 gives fused bicyclic dihydroisoxazole product 101 in 58% yield.…”
Section: Photocatalyzed Reactionsmentioning
confidence: 99%