From Aldehyde to Ketone via Water‐Accelerated Molybdenum‐Photocatalysis

ChemCatChem, Journal Year: 2024, Volume and Issue: 16(21)

Published: July 16, 2024

Abstract The efficient “on water” protocol was developed by employing molybdenum‐based polyoxometalate [N(C 4 H 9 ) ] 2 [Mo 6 O 19 as the photocatalyst. This water‐accelerated photoinduced process affords versatile ketones from aldehydes straightforwardly, showcasing exceptional substrate generality. Its applicability to life‐related molecules such amino acids, peptides, and sugars, further demonstrates its potential for bioorthogonal application. mechanistic investigation highlights hydrogen atom transfer (HAT) between excited‐state POM benzaldehyde acyl radical formation. highly reactive is readily trapped Michael acceptor, thereby enabling subsequent C−H functionalization. Highly gram‐scale flow operation underlines industrial of this transformative strategy.

Language: Английский

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Asymmetric Allylation of Aldoxime Derivatives with β‐Amidoallylboronate in Water and Its Application to Divergent Synthesis of N‐Hydroxy‐γ‐Lactam and 1,2‐Oxazinan‐6‐one

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(15)

Published: April 17, 2024

Abstract A new application involving a water–stable amido–functionalized allylboronate has been developed for 1,2‐addition to carbon–nitrogen double bonds. The process achieves highly enantioselective allylation of aldoxime derivatives in water, by employing O ‐Boc oximes as substrates under Zn(OH) 2 –chiral aminophenol catalysis. This affords the corresponding homoallylic amines with 91–96 % ee. products could be transformed into N ‐hydroxy‐γ‐lactam or 1,2‐oxazinan‐6‐one, through an acidic protection‐acidic treatment sequence, respectively, almost without enantiopurity loss.

Language: Английский

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Small-Molecule-Based Strategy for Mitigating Deactivation of Chiral Lewis Acid Catalysis

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(33), P. 22918 - 22922

Published: Aug. 6, 2024

Chiral Lewis acid catalysts are widely used in organic synthesis due to their diverse applications. However, high acidity makes them susceptible deactivation by basic reagents and water. Here, we present a novel strategy for mitigating this using small molecules. By incorporating weakly coordinating anions into the secondary coordination sphere of metal center, designed highly reusable chiral complex. This complex exhibits excellent thermal stability allows use electron-poor nucleophiles reactions. Spectroscopic titration studies confirmed robustness optimized work provides valuable insights overcoming limitations acids environments, expanding potential chemical synthesis.

Language: Английский

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Vigorously Stirred La2O3 Suspensions for Michael Additions in Water

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(73), P. 9994 - 9996

Published: Jan. 1, 2024

Vigorously stirred La 2 O 3 suspensions in water demonstrated exceptional efficiency ( e.g. high yields, short reaction times) for carbon–carbon bond formation. Water proved irreplaceable by organic solvents despite the reactant(s) being immiscible.

Language: Английский

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Efficient Separation and Extraction of Guaiacol and its Derivatives from Bio-Oils Based on a Heterogeneous Extraction Technique

Published: Jan. 1, 2024

Language: Английский

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Efficient separation and extraction of guaiacol and its derivatives from bio-oils based on a heterogeneous extraction technique

Separation and Purification Technology, Journal Year: 2024, Volume and Issue: unknown, P. 129739 - 129739

Published: Sept. 1, 2024

Language: Английский

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