“On-Water” accelerated dearomative cycloaddition via aquaphotocatalysis

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: May 8, 2024

Abstract Sulfur(VI) fluoride exchange (SuFEx) has emerged as an innovative click chemistry to harness the pivotal connectivity of sulfonyl fluorides. Synthesizing such alkylated S(VI) molecules through a straightforward process is paramount importance, and their water-compatibility opens door plethora applications in biorelevant materials chemistry. Prior aquatic endeavors have primarily focused on delivering catalysts involving ionic mechanisms, studies regarding visible-light photocatalytic transformation are unprecedented. Herein we report on-water accelerated dearomative aquaphotocatalysis for heterocyclic alkyl SuFEx hubs. Notably, water exerts pronounced accelerating effect [2 + 2] cycloaddition between (hetero)arylated ethenesulfonyl fluorides inert heteroaromatics. This phenomenon likely due high-pressure-like reactivity amplification at water-oil interface. Conventional solvents proved totally ineffective, leading isomerization starting material.

Language: Английский

---

Sustainable click reactions: Use of greener reaction media in the synthesis of 1,2,3-triazoles

Tetrahedron, Journal Year: 2024, Volume and Issue: 157, P. 133964 - 133964

Published: March 31, 2024

Language: Английский

---

Single-Handed Helical Polymer-Based Polycarboxylate with Achiral Triarylphosphine Pendants as Chiral Catalysts for Asymmetric Cross-Coupling Reactions in Pure Water

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 28, 2025

Helical poly(quinoxaline-2,3-diyl)s (PQX) containing chiral carboxylic acid side chains derived from natural l-lactic were synthesized. The newly synthesized helical polycarboxylated polymer was soluble in basic pure water by forming polycarboxylate and adopted the P-helical conformation (right-handed), whereas M-helical is predominant under weakly acidic aqueous conditions. water-soluble PQX additional monomer units bearing a 2-(diarylphosphino)phenyl group employed asymmetric Suzuki-Miyaura coupling reaction absence of organic cosolvents. Remarkable enantioselectivities up to 99% ee, which found be higher than same solvent using corresponding lipophilic PQX, obtained for couplings 2-substituted 1-halonaphthalenes. It presumed that hydrophobic environment provided main chain according Nile Red-based hydrophobicity test. Recovery crude product without any trace has been demonstrated switch solubility depending on pH.

Language: Английский

---

Replacing polar aprotic solvents with water in organic synthesis

Current Opinion in Green and Sustainable Chemistry, Journal Year: 2023, Volume and Issue: 40, P. 100774 - 100774

Published: Feb. 3, 2023

Language: Английский

---

Exporting Metal‐Carbene Chemistry to Live Mammalian Cells: Copper‐Catalyzed Intracellular Synthesis of Quinoxalines Enabled by N−H Carbene Insertions

Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 60(40), P. 22017 - 22025

Published: Aug. 13, 2021

Implementing catalytic organometallic transformations in living settings can offer unprecedented opportunities chemical biology and medicine. Unfortunately, the number of biocompatible reactions so far discovered is very limited, essentially restricted to uncaging processes. Here, we demonstrate viability performing metal carbene transfer live mammalian cells. In particular, show that copper (II) catalysts promote intracellular annulation alpha-keto diazocarbenes with ortho-amino arylamines, a process initiated by an N-H insertion. The potential this transformation underscored cellulo synthesis product alters mitochondrial functions, demonstrating cell selective biological responses using targeted catalysts. Considering wide reactivity spectrum carbenes, work opens door significantly expanding repertoire life-compatible abiotic reactions.

Language: Английский

---

Asymmetric Michael Addition in Synthesis of β-Substituted GABA Derivatives

Molecules, Journal Year: 2022, Volume and Issue: 27(12), P. 3797 - 3797

Published: June 13, 2022

γ-Aminobutyric acid (GABA) represents one of the most prolific structural units widely used in design modern pharmaceuticals. For example, β-substituted GABA derivatives are found numerous neurological drugs, such as baclofen, phenibut, tolibut, pregabalin, phenylpiracetam, brivaracetam, and rolipram, to mention just a few. In this review, we critically discuss literature data reported on preparation substituted using Michael addition reaction key synthetic transformation. Special attention is paid asymmetric methods featuring synthetically useful stereochemical outcomes operational simplicity.

Language: Английский

---

Recent advances in the synthesis of active pharmaceutical and agrochemical ingredients in micellar media

Current Opinion in Green and Sustainable Chemistry, Journal Year: 2022, Volume and Issue: 39, P. 100729 - 100729

Published: Nov. 26, 2022

Language: Английский

---

Water-soluble diphosphine ligands for rhodium-catalyzed branch-selective hydroaminomethylation of vinyl arenes with anilines in water

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(11), P. 4420 - 4424

Published: Jan. 1, 2022

Rhodium-catalyzed hydroaminomethylation of various vinyl arenes with anilines has been accomplished using water as an environmentally benign reaction media.

Language: Английский

---

[DABCO-C18]Br: A novel basic surfactant for the synthesis of dihydropyrano[3,2-c]chromenes and 2-aminobenzochromenes under ambient conditions

Journal of Molecular Liquids, Journal Year: 2023, Volume and Issue: 391, P. 123247 - 123247

Published: Oct. 5, 2023

Language: Английский

---

The Aldol Reaction: Group XIV Enolates

Elsevier eBooks, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

---