Arylation of ortho-Hydroxyarylenaminones by Sulfonium Salts and Arenesulfonyl Chlorides: An Access to Isoflavones

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(7), P. 4896 - 4916

Published: March 15, 2021

Herein we disclose three new methods for the straightforward and efficient synthesis of 3-arylchromones following arylation ortho-hydroxyarylenaminones by vast diversities bench-stable easy-to-use sulfonium salts arenesulfonyl chlorides. Both developed methods, namely light-mediated photoredox electrophilic arylation, showed good efficiency, are feasible preparation in good-to-excellent yields. This work showcases first described attempt where chlorides were successfully utilized construction chromone heterocycle system.

Language: Английский

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Pd-catalyzed relay Heck arylation of alkenyl alcohols with arylsulfonium salts

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(15), P. 4219 - 4230

Published: Jan. 1, 2024

The Pd-catalyzed relay Heck arylation of alkenyl alcohols with arylsulfonium salts is first reported for synthesizing arylalkyl ketones or aldehydes.

Language: Английский

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Cross-Electrophile Couplings of Benzyl Sulfonium Salts with Thiosulfonates via C–S Bond Activation

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13601 - 13607

Published: Sept. 4, 2024

A zinc-mediated cross-electrophile coupling of benzyl sulfonium salts with thiosulfonates via C-S bond cleavage was achieved. The reductive thiolation proceeded well under transition metal-free conditions to afford the desired sulfides in good yields, exhibiting both broad substrate scope and functionality tolerance. In addition, reaction could be applied use selenosulfonate as an effective selenylation agent subjected scale-up synthesis.

Language: Английский

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Electronic Structures of Nickel(II)-Bis(indanyloxazoline)-dihalide Catalysts: Understanding Ligand Field Contributions That Promote C(sp²)–C(sp³) Cross-Coupling

Inorganic Chemistry, Journal Year: 2023, Volume and Issue: 62(34), P. 14010 - 14027

Published: Aug. 16, 2023

NiII(IB) dihalide [IB = (3aR,3a′R,8aS,8a′S)-2,2′-(cyclopropane-1,1-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]-oxazole)] complexes are representative of a growing class first-row transition-metal catalysts for the enantioselective reductive cross-coupling C(sp2) and C(sp3) electrophiles. Recent mechanistic studies highlight complexity these ground-state cross-couplings but also illuminate new reactivity pathways stemming from one-electron redox their significant sensitivities to reaction conditions. For first time, diverse array spectroscopic methods coupled electrochemistry have been applied NiII-based precatalysts evaluate specific ligand field effects governing key Ni-based potentials. We experimentally demonstrate DMA solvent coordination catalytically relevant Ni complexes. Coordination is shown favorably influence redox-based steps prevent other deleterious equilibria. Combined with electronic structure calculations, we further provide direct correlation between intermediate frontier molecular orbital energies yields. Considerations developed herein use synergic electrochemical concepts catalyst design rationalization condition optimization.

Language: Английский

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Cobalt-Catalyzed Reductive Cross-Coupling To Construct Csp³–Csp³ Bonds via Csp³–S and Csp³–X Bonds Activation

Organic Letters, Journal Year: 2023, Volume and Issue: 25(42), P. 7689 - 7693

Published: Oct. 18, 2023

A cross-electrophilic coupling of benzyl sulfonium salts with alkyl halides forming Csp3–Csp3 bonds is described by using a Co-based catalytic system. The activation the stable Csp3–S bond under mild reaction conditions leads to various functionalized derivatives. Preliminary mechanistic studies suggest involvement radicals formed from both and sulfoniums through single electron transfer.

Language: Английский

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