2023
DOI: 10.1039/d2sc06801j
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Merging the Norrish type I reaction and transition metal catalysis: photo- and Rh-promoted borylation of C–C σ-bonds of aryl ketones

Abstract: Synthesis of arylboronates via borylation of C–C σ-bonds of aryl ketones was achieved by the combined use of photoenergy and a Rh catalyst.

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Cited by 5 publications
(4 citation statements)
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“…Surprisingly, the same product was obtained by a Norrish type I reaction of ketone when 2-aminophenone was used as the substrate (Table 3). 38–41 Under the optimized conditions, 2-aminophenone and tetrahydroisoquinoline afforded the desired product 4a in 50% yield. Halogenated 2-aminophenones, such as those having –F,–Cl, and –Br substituents, effectively afforded the desired quinazolines under the established conditions, with yields of 51%, 70%, 55%, and 55%, respectively.…”
Section: Resultsmentioning
confidence: 99%
“…Surprisingly, the same product was obtained by a Norrish type I reaction of ketone when 2-aminophenone was used as the substrate (Table 3). 38–41 Under the optimized conditions, 2-aminophenone and tetrahydroisoquinoline afforded the desired product 4a in 50% yield. Halogenated 2-aminophenones, such as those having –F,–Cl, and –Br substituents, effectively afforded the desired quinazolines under the established conditions, with yields of 51%, 70%, 55%, and 55%, respectively.…”
Section: Resultsmentioning
confidence: 99%
“…A possible mechanism is outlined in Scheme 15. Irradiation of ClÀ BP with 20 W 365 nm LEDs gives excited ClÀ BP (ClÀ BP*), which could abstract a hydrogen from the toluene to afford [ClÀ BPÀ H] * and benzyl radical (24). Simultaneously, oxidative addition of the N-acylsuccinimide derivative (25) to L n Ni 0 (26) generated intermediate 27.…”
Section: N-acylsuccinimides As Acylation Reagentsmentioning
confidence: 99%
“…In 2023, Takaya and coworkers reported the synthesis of arylboronates via borylation of the C−C σ‐bonds of aryl ketones, enabled by a combination of photoenergy and Rh catalysis (Scheme 27). [24] A series of pivalophenone with electron‐donating or electron‐withdrawing groups on the para position of the phenyl rings delivered the desired arylboronates in good yields. However, 4‐Ph substituted pivalophenone was not a suitable substrate for this reaction.…”
Section: Borylationmentioning
confidence: 99%
“…Recently, the Takaya group reported a borylation reaction via decarbonylation, where acyl radicals generated under photoirradiation through Norrish Type I reaction are converted into acyl metal species using a transition metal catalyst. 37 This novel approach allows for the functionalization of nonactivated ketones in a single step, although the reaction is limited to borylation. Inspired by these works, we embarked on developing a versatile decarbonylative cross-coupling reaction that can react with a multitude of nucleophiles in a single step.…”
Section: Introductionmentioning
confidence: 99%