Rh(iii)-Catalyzed sequential ortho-C–H oxidative arylation/cyclization of sulfoxonium ylides with quinones toward 2-hydroxy-dibenzo[b,d]pyran-6-ones

Chemical Communications, Journal Year: 2020, Volume and Issue: 56(49), P. 6688 - 6691

Published: Jan. 1, 2020

A rhodium(iii)-catalyzed ortho-C-H functionalization of sulfoxonium ylides followed by intramolecular annulation reactions with quinones was described, where the carbonyl in served as a chelation group. This protocol leads to efficient formation 2-hydroxy-6H-benzo[c]chromen-6-one derivatives, proceeding cleavage C(O)-S bond ylides. featured high chemo-selectivity and functional group tolerance, acted aroyl sources.

Language: Английский

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Rh(III)‐Catalyzed Diverse C—H Functionalization of Iminopyridinium Ylides

Chinese Journal of Chemistry, Journal Year: 2021, Volume and Issue: 39(9), P. 2489 - 2494

Published: May 9, 2021

Main observation and conclusion Divergent synthesis of useful skeletons has been realized via rhodium(III)‐catalyzed C—H activation iminopyridinium ylides coupling with various unsaturated reagents. Isocoumarins isoquinolones were obtained cleavage the C—N or N—N bond in ylidic directing group, while fluorinated alkenes delivered group intact. The reactions occurred wide substrate scopes good efficiency under redox‐neutral air‐tolerant conditions. Representative products exhibit solid‐state fluorescent property bioactivity inhibition toward human cancer cells.

Language: Английский

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α-Carbonyl sulfoxonium ylides in transition metal-catalyzed C–H activation: a safe carbene precursor and a weak directing group

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 21(5), P. 879 - 909

Published: Dec. 6, 2022

Transition metal-catalyzed cross-coupling of sp2 C-H bonds with diazo compounds via carbene migratory insertion represents an efficient strategy for the construction C-C and C-heteroatom in organic synthesis. Despite popularity as coupling partners activation, they pose serious safety stability issues due to potential exothermic reactions linked release N2 gas. However, compared compounds, sulfoxonium ylides are generally crystalline solids, more stable, widely used industrial scales, easier/safer prepare. Therefore, recent years have witnessed upsurge employing α-carbonyl alternative surrogate transition activation. Unlike contain inherent serve a partner well weak directing group. This review will summarize progress made both categories reactions.

Language: Английский

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Hydroxyl-Directed Ruthenium-Catalyzed peri-Selective C–H Acylmethylation and Annulation of Naphthols with Sulfoxonium Ylides

Organic Letters, Journal Year: 2021, Volume and Issue: 23(16), P. 6200 - 6205

Published: Aug. 2, 2021

Herein, we report a highly efficient ruthenium-catalyzed peri-selective C(sp2)–H acylmethylation of 1-naphthols with α-carbonyl sulfoxonium ylides by utilizing hydroxyl as weakly coordinating directing group. This new method imparts good reactivity, excellent chemo- and regioselectivity, broad functional group tolerance involves mild reaction conditions. The C–H acylmethylated products can be readily cyclized into fluorescent annulated pyrans one-pot process.

Language: Английский

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Synthesis of Tetrahydro-2H-thiopyran 1,1-Dioxides via [1+1+1+1+1+1] Annulation: An Unconventional Usage of a Tethered C–S Synthon

Organic Letters, Journal Year: 2022, Volume and Issue: 24(41), P. 7659 - 7664

Published: Oct. 10, 2022

An unprecedented [1+1+1+1+1+1] annulation process has been developed for the construction of tetrahydro-2H-thiopyran 1,1-dioxides. Notably, rongalite acted as a tethered C-S synthon in this reaction and can be chemoselectively used triple C1 units source sulfone. Mechanistic investigation indicated that two different carbon-increasing models are involved which serves units.

Language: Английский

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Regioselective and Chemodivergent Synthesis of Azulenolactones and Azulenolactams from Rhodium(III)‐Catalyzed Reactions of Azulenecarboxamides with Sulfoxonium Ylides

Advanced Synthesis & Catalysis, Journal Year: 2020, Volume and Issue: 363(2), P. 512 - 524

Published: Nov. 4, 2020

Abstract A regioselective and chemodivergent synthetic approach for azulenolactones azulenolactams as a new scaffold was demonstrated through Rh(III)‐catalyzed reaction of N ‐methoxyazulene‐1‐carboxamides with sulfoxonium ylides. Sulfoxonium ylides that act precursor secondary carbene described, leading to the selective formation bearing two substituents on newly introduced double bond. This method functionalization less reactive 2‐position azulene overcome natural reactivity. magnified image

Language: Английский

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Recent Advances on Synthetic Methodology Merging C–H Functionalization and C–C Cleavage

Molecules, Journal Year: 2020, Volume and Issue: 25(24), P. 5900 - 5900

Published: Dec. 13, 2020

The functionalization of C–H bonds has become a major thread research in organic synthesis that can be assessed from different angles, for instance depending on the type catalyst employed or overall transformation is carried out. This review compiles recent progress synthetic methodology merges along with cleavage C–C bonds, either intra- intermolecular fashion. manuscript organized two main sections according to substrate which bond takes place, basically attending scission strained unstrained bonds. Furthermore, related works have been grouped basis mechanistic aspects transformations are out, i.e.,: (a) classic transition metal catalysis where organometallic intermediates involved; (b) processes occurring via radical generated through use initiators photochemically; and (c) reactions catalyzed mediated by suitable Lewis Brønsted acid bases, molecular rearrangements take place. Thus, throughout wide range approaches show combination single operations serve as platform achieve complex skeletons straightforward manner, among them interesting carbo- heterocyclic scaffolds.

Language: Английский

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Easy synthesis of imidazo[1,5-a]indol-3-ones through Rh(iii)-catalyzed C–H allenylation/annulation

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(90), P. 12012 - 12015

Published: Jan. 1, 2021

A highly efficient and regioselective synthesis of imidazo[1,5-a]indol-3-ones has been developed via a sequential C-H allenylation/annulation starting from easily available N-methoxycarbamoyl indoles propargyl alcohols, in which the alcohols served as C1 synthon. This strategy displays excellent regioselectivity, high atom economy tolerates broad substrate scope.

Language: Английский

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Recent advances in synthesis of isocoumarins: An overview

Tetrahedron, Journal Year: 2023, Volume and Issue: 150, P. 133740 - 133740

Published: Nov. 12, 2023

Language: Английский

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Rhodium(II)-catalyzed multicomponent assembly of α,α,α-trisubstituted esters via formal insertion of O–C(sp3)–C(sp2) into C–C bonds

Nature Communications, Journal Year: 2020, Volume and Issue: 11(1)

Published: Aug. 24, 2020

Language: Английский

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