Photopromoted carbonylation of bromobenzene under ambient conditions

Mu, Li Zhuo; Jia, Ying Ping; Yin, Jing; Zhou, Guang Yun; Cui, Ying; Gao, Da Bin

doi:10.1016/j.cclet.2009.01.008

Cited by 10 publications

(2 citation statements)

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“…Cobalt salts have been found to efficiently catalyze the carbonylation of alkenes, chloro and bromoalkanes under UV irradiation [55][56][57][58][59]. The first report on visible-light-mediated cobalt-catalyzed carbonylation reaction appeared in 2012, when Jia, Yin and colleagues, based on their previous findings [60], developed a Co(OAc) 2 -catalyzed alkoxycarbonylation of aryl bromides under visible-light irradiation and mild conditions (Scheme 30) [61]. The use of a strong base (NaOMe) and an organic sensitizer (PhCOPh) was essential to the reaction's success.…”

Section: Visible-light-promoted Cobalt-catalyzed Carbonylationsmentioning

confidence: 99%

Advances in Visible-Light-Mediated Carbonylative Reactions via Carbon Monoxide (CO) Incorporation

et al. 2021

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The abundant and inexpensive carbon monoxide (CO) is widely exploited as a C1 source for the synthesis of both fine and bulk chemicals. In this context, photochemical carbonylation reactions have emerged as a powerful tool for the sustainable synthesis of carbonyl-containing compounds (esters, amides, ketones, etc.). This review aims at giving a general overview on visible light-promoted carbonylation reactions in the presence of metal (Palladium, Iridium, Cobalt, Ruthenium, Copper) and organocatalysts as well, highlighting the main features of the presented protocols and providing useful insights on the reaction mechanisms.

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Section: Visible-light-promoted Cobalt-catalyzed Carbonylationsmentioning

confidence: 99%

Advances in Visible-Light-Mediated Carbonylative Reactions via Carbon Monoxide (CO) Incorporation

et al. 2021

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“…Then, in 2009, Jia's group reported a Co(OAc) 2 triggered methoxycarbonylation of phenyl bromides 7 under high energy light irradiation (λ max = 200−450 nm) to access the methyl benzoate 3 (Scheme 7). 26 In this strategy, PhCOMe and CH 3 ONa were utilized as photosensitizer and basic additive, respectively, at ambient temperature. Here, the role of basic additives was to neutralize the accumulation of HBr to maintain the pH of the reaction.…”

Section: Alkoxy-and Hydroxycarbonylation (Synthesis Of Esters and Car...mentioning

confidence: 99%

Photocatalytic Carbonylation Strategies: A Recent Trend in Organic Synthesis

Singh

Sharma

2020

J. Org. Chem.

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In the last few decades, photocatalytic radical carbonylation strategies have received considerable attention as they are becoming a formidable tool in the toolbox of organic synthesis. These carbonylation strategies involve the incorporation of a carbon monoxide into organic molecules in an atom-and step-economical manner. Mostly, these strategies rely on the generation of an acyl radical as a key intermediate, which would be created via incorporation of CO molecule to an alkyl/aryl radical. The production of alkyl/aryl radical in these methodologies required either the high-intensity lightinduced transition-metal (TM)-catalyzed systems or visible-lightinduced photocatalytic systems that would be capable of mediating single electron transfer (SET) to the C(sp 3 )-or C(sp 2 )-hybridized coupling partners. Here, in this review, the development in the field of photocatalytic carbonylation is described by compiling the literature of the last 40 years, and their reaction mechanisms have been emphatically discussed. In addition, to aid readers, we have assimilated redox potentials of photocatalysts and substrates for a better sense of spontaneity of these photoredox carbonylation reactions.

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