Nanolayered cobalt–molybdenum sulphides (Co–Mo–S) catalyse borrowing hydrogen C–S bond formation reactions of thiols or H<sub>2</sub>S with alcohols

Sorribes, Iván; Corma, Avelino

doi:10.1039/c8sc05782f

Cited by 36 publications

(23 citation statements)

References 188 publications

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“…13 C NMR (500 MHz, CDCl 3 , 300 K), δ (ppm): 137.51, 134.1, 132.47, 132.05, 128.99, 128.67, 127.85, 127.57, 127.36, 127.29, 126.76, 126.60, 126.35, 125.87, 39.09. NMR data are consistent with the reported literature …”

Section: Methodssupporting

confidence: 92%

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Mono- and Dinuclear α-Diimine Nickel(II) and Palladium(II) Complexes in C–S Cross-Coupling

et al. 2020

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The usefulness of transition metal catalytic systems in C–S cross-coupling reactions is significantly reduced by air and moisture sensitivity, as well as harsh reaction conditions. Herein, we report four highly air- and moisture-stable well-defined mononuclear and bridged dinuclear α-diimine Ni(II) and Pd(II) complexes for C–S cross-coupling. Various ligand frameworks, including acenaphthene- and iminopyridine-based ligands, were employed, and the resulting steric properties of the catalysts were evaluated and correlated with reaction outcomes. Under aerobic conditions and low temperatures, both Ni and Pd systems exhibited broader substrate scope and functional group tolerance than previously reported catalysts. Over 40 compounds were synthesized from thiols containing alkyl, benzyl, and heteroaryl groups. Also, pharmaceutically active heteroaryl moieties are incorporated from thiol and halide sources. Notably, the bridged dinuclear five-coordinate Ni complex has outperformed the remaining three mono four- or six-coordinate complexes by giving almost quantitative yields across a broad substrate scope.

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Section: Methodssupporting

confidence: 92%

“…ESI-MS m/z [M + H] + = 301.0103 (calculated for C 20 H 28 S, 301.0089). 1 52 4-(Phenylthio)pyridine (CD6). Silica gel column chromatography having eluent as n-hexane and ethyl acetate of 10:1 (v/v).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Mono- and Dinuclear α-Diimine Nickel(II) and Palladium(II) Complexes in C–S Cross-Coupling

et al. 2020

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“…p-methoxybenzyl thiol 43 (4j): The aqueous layer on acidified with concentrated HCl to pH=2, then extract with ether (25 mL X 2), wash the ether layer with water (50 mL), brine solution (50 mL), dried over MgSO4 and filter. The filtrate was concentrated to give thiol 4i as residual…”

Section: Bis(p-methoxybenzyl) Disulfide 42 (7j)mentioning

confidence: 99%

A Convenient Synthesis of Thiol, Trithiocarbonate and Disulfide

Gondi

Rissing²,

Son³

2021

Preprint

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<div>Synthesis of unsymmetrical trithiocarbonate sulfonate salt, along with disulfide, thiol and</div><div>symmetrical trithiocarbonate from 3-mercapto-1-propane-sulfonicacid, sodium salt with, without</div><div>of phase transfer catalyst and under various reaction conditions are described. The obtained</div><div>compounds having divergent usefulness in RAFT polymerization, sulfonyl preparation and</div><div>having capable of binding in a multidentate fashion to soft transition metal ions.</div>

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“… 93 In the following years, we prepared cobalt–molybdenum sulfides (Co–Mo–S) with tunable phase composition that displayed enhanced catalytic activity for the chemo- and regioselective hydrogenation of quinoline derivatives 94 and for the borrowing hydrogen synthesis of thioethers from alcohols. 95 Later on, bimetallic iron molybdenum selenides were applied as catalysts for the preparation of pyrrolo[1,2- a ]quinoxalines from o -nitroanilines. 96 …”

Section: Introductionmentioning

confidence: 99%

Molecularly Engineering Defective Basal Planes in Molybdenum Sulfide for the Direct Synthesis of Benzimidazoles by Reductive Coupling of Dinitroarenes with Aldehydes

Rodenes

Gonell

Martı́n

et al. 2022

JACS Au

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Developing more sustainable catalytic processes for preparing N-heterocyclic compounds in a less costly, compact, and greener manner from cheap and readily available reagents is highly desirable in modern synthetic chemistry. Herein, we report a straightforward synthesis of benzimidazoles by reductive coupling of o -dinitroarenes with aldehydes in the presence of molecular hydrogen. An innovative molecular cluster-based synthetic strategy that employs Mo 3 S 4 complexes as precursors have been used to engineer a sulfur-deficient molybdenum disulfide (MoS 2 )-type material displaying structural defects on both the naturally occurring edge positions and along the typically inactive basal planes. By applying this catalyst, a broad range of functionalized 2-substituted benzimidazoles, including bioactive compounds, can be selectively synthesized by such a direct hydrogenative coupling protocol even in the presence of hydrogenation-sensitive functional groups, such as double and triple carbon–carbon bonds, nitrile and ester groups, and halogens as well as diverse types of heteroarenes.

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Nanolayered cobalt–molybdenum sulphides (Co–Mo–S) catalyse borrowing hydrogen C–S bond formation reactions of thiols or H₂S with alcohols

Abstract: Nanolayered cobalt–molybdenum sulphide (Co–Mo–S) materials have been established as excellent catalysts for C–S bond construction.

Cited by 36 publications

References 188 publications

Mono- and Dinuclear α-Diimine Nickel(II) and Palladium(II) Complexes in C–S Cross-Coupling

Mono- and Dinuclear α-Diimine Nickel(II) and Palladium(II) Complexes in C–S Cross-Coupling

A Convenient Synthesis of Thiol, Trithiocarbonate and Disulfide

Molecularly Engineering Defective Basal Planes in Molybdenum Sulfide for the Direct Synthesis of Benzimidazoles by Reductive Coupling of Dinitroarenes with Aldehydes

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Nanolayered cobalt–molybdenum sulphides (Co–Mo–S) catalyse borrowing hydrogen C–S bond formation reactions of thiols or H2S with alcohols

Abstract: Nanolayered cobalt–molybdenum sulphide (Co–Mo–S) materials have been established as excellent catalysts for C–S bond construction.

Cited by 36 publications

References 188 publications

Mono- and Dinuclear α-Diimine Nickel(II) and Palladium(II) Complexes in C–S Cross-Coupling

Mono- and Dinuclear α-Diimine Nickel(II) and Palladium(II) Complexes in C–S Cross-Coupling

A Convenient Synthesis of Thiol, Trithiocarbonate and Disulfide

Molecularly Engineering Defective Basal Planes in Molybdenum Sulfide for the Direct Synthesis of Benzimidazoles by Reductive Coupling of Dinitroarenes with Aldehydes

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Nanolayered cobalt–molybdenum sulphides (Co–Mo–S) catalyse borrowing hydrogen C–S bond formation reactions of thiols or H₂S with alcohols