Cobalt-catalyzed photopromoted carbonylation of chloroalkanes in the presence of KI

Jia, Ying Ping; Cui, Ying; Yin, Jing; Zhou, Guang Yun; Li, Shen Min; Gao, Da Bin; Wang, Xiang-Sheng

doi:10.1016/j.cclet.2010.04.027

Cited by 9 publications

(5 citation statements)

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“…Compound 7 shows only a weak absorbance in the NIR at 1159 nm and in the visible range at 444 nm. All seven compounds show a peak in the UV region around 260 nm, which has been assigned as an LMCT from the thioacetate backbone, primarily from Pt to S because the monometallic {K 2 [Pt(SAc) 4 ]} displays a similar absorption at 257 nm (21,700 cm –1 M –1 ), whereas the metal acetate {Co(OAc) 2 } displays a much weaker absorption (100 cm –1 M –1 ) near this energy …”

Section: Resultsmentioning

confidence: 99%

Thiocyanate-Ligated Heterobimetallic {PtM} Lantern Complexes Including a Ferromagnetically Coupled 1D Coordination Polymer

et al. 2016

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A series of heterobimetallic lantern complexes with the central unit {PtM(SAc)4(NCS)} have been prepared and thoroughly characterized. The {Na(15C5)}[PtM(SAc)4(NCS)] series, 1 (Co), 2 (Ni), 3 (Zn), are discrete compounds in the solid state, whereas the {Na(12C4)2)}[PtM(SAc)4(NCS)] series, 4 (Co), 5 (Ni), 6 (Zn), and 7 (Mn), are ion-separated species. Compound 7 is the first {PtMn} lantern of any bridging ligand (carboxylate, amide, etc.). Monomeric 1-7 have M(2+), necessitating counter cations that have been prepared as {(15C5)Na}(+) and {(12C4)2Na}(+) variants, none of which form extended structures. In contrast, neutral [PtCr(tba)4(NCS)]∞ 8 forms a coordination polymer of {PtCr}(+) units linked by (NCS)(-) in a zigzag chain. All eight compounds have been thoroughly characterized and analyzed in comparison to a previously reported family of compounds. Crystal structures are presented for compounds 1-6 and 8, and solution magnetic susceptibility measurements are presented for compounds 1, 2, 4, 5, and 7. Further structural analysis of dimerized {PtM} units reinforces the empirical observation that greater charge density along the Pt-M vector leads to more Pt···Pt interactions in the solid state. Four structural classes, one new, of {MPt}···{PtM} units are presented. Solid state magnetic characterization of 8 reveals a ferromagnetic interaction in the {PtCr(NCS)} chain between the Cr centers of J/kB = 1.7(4) K.

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Section: Resultsmentioning

confidence: 99%

Thiocyanate-Ligated Heterobimetallic {PtM} Lantern Complexes Including a Ferromagnetically Coupled 1D Coordination Polymer

et al. 2016

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“…In addition to methoxycarbonylation of aryl or vinyl bromides/chlorides and bromoalkanes, the cobalt-catalyzed methoxycarbonylation of choloroalkanes 15 under UV-light irradiation (λ max = 254 nm) at ambient temperature was disclosed by Wang and co-workers in 2010 (Scheme 8). 27 However, both Co(OAc) 2 and CoCl 2 as catalysts were found to be equally effective for this reaction, and KI acted as a promoter. In this strategy, the basic additive (NaOAc) played a crucial role not only in neutralizing HCl but also in generating Co(OAc) 2 via acetate exchange between NaOAc and CoCl 2 .…”

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

confidence: 94%

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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“…In 2010, Jia et al described the cobalt-catalyzed photocatalytic methyl carbonylation of chlorinated alkanes using carbon monoxide with iodide under UV light irradiation and ambient conditions (Scheme 9a). [63] In this three-component reaction, a cobalt compound (Co(OAc) 2 or CoCl 2 ) was used as the photocatalyst, while CO and methanol were used as C 1 sources. Under optimal reaction conditions, the carbonylation product of chlorocyclohexane was methyl cyclohexanecarboxylate, and the yield and selectivity were approximately 40 % and 87 %, respectively.…”

Section: Other Cà C Coupling Reactions Using Methanol As the C 1 Sourcementioning

confidence: 99%

“…In 2010, Jia et al. described the cobalt‐catalyzed photocatalytic methyl carbonylation of chlorinated alkanes using carbon monoxide with iodide under UV light irradiation and ambient conditions (Scheme 9a) [63] . In this three‐component reaction, a cobalt compound (Co(OAc) 2 or CoCl 2 ) was used as the photocatalyst, while CO and methanol were used as C 1 sources.…”

Section: Transformation Of Methanol Induced By Molecular Photocatalystsmentioning

confidence: 99%

Photo‐Induced C₁ Substitution Using Methanol as a C₁ Source

Liu

et al. 2023

ChemSusChem

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The development of sustainable and efficient C1 substitution methods is of central interest for organic synthesis and pharmaceuticals production, the methylation motifs bound to a carbon, nitrogen, or oxygen atom widely exist in natural products and top‐selling drugs. In the past decades, a number of methods involving green and inexpensive methanol have already been disclosed to replace industrial hazardous and waste‐generating C1 source. Among the various efforts, photochemical strategy is considered as a “renewable” alternative that shows great potential to selectively activate methanol to achieve a series of C1 substitutions at mild conditions, typically C/N‐methylation, methoxylation, hydroxymethylation, and formylation. Herein the recent advances in selective transformation of methanol to various C1 functional groups via well‐designed photochemical systems involving different types of catalysts or not is systematically reviewed. Both the mechanism and corresponding photocatalytic system were discussed and classified on specific methanol activation models. Finally, the major challenges and perspectives are proposed.

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Cobalt-catalyzed photopromoted carbonylation of chloroalkanes in the presence of KI

Cited by 9 publications

References 5 publications

Thiocyanate-Ligated Heterobimetallic {PtM} Lantern Complexes Including a Ferromagnetically Coupled 1D Coordination Polymer

Thiocyanate-Ligated Heterobimetallic {PtM} Lantern Complexes Including a Ferromagnetically Coupled 1D Coordination Polymer

Photocatalytic Carbonylation Strategies: A Recent Trend in Organic Synthesis

Photo‐Induced C₁ Substitution Using Methanol as a C₁ Source

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Cobalt-catalyzed photopromoted carbonylation of chloroalkanes in the presence of KI

Cited by 9 publications

References 5 publications

Thiocyanate-Ligated Heterobimetallic {PtM} Lantern Complexes Including a Ferromagnetically Coupled 1D Coordination Polymer

Thiocyanate-Ligated Heterobimetallic {PtM} Lantern Complexes Including a Ferromagnetically Coupled 1D Coordination Polymer

Photocatalytic Carbonylation Strategies: A Recent Trend in Organic Synthesis

Photo‐Induced C1 Substitution Using Methanol as a C1 Source

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Photo‐Induced C₁ Substitution Using Methanol as a C₁ Source