Enlightening the Unconventional Photocatalytic Space in Organic Transformation DOI Open Access
Milan Pramanik

Prayogik Rasayan, Journal Year: 2023, Volume and Issue: 7(1)

Published: Jan. 1, 2023

In recent years, organic photo-redox catalysts such as Ru or Ir-metal complexes and dyes have expanded the traditional catalytic toolbox due to their sustainability environment friendliness. The central focus of this review is explore unconventional photo-catalysts activity in transformations. However, an overview unorthodox has been demonstrated herein illuminate photocatalytic space synthesis.

Language: Английский

Manganese-Promoted Electrochemical Imino-Pinacol Coupling to Access Vicinal Diamines DOI

Weihao Cui,

Xiaolong Xu, Cong Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 5, 2025

We herein introduce an electrochemical imino-pinacol coupling reaction to access the vicinal diamine scaffold. This green and convenient protocol employs in situ-generated imines as starting materials deliver a broad range of products under electroreductive conditions. Moreover, this is also applicable pinacol coupling. Mechanistic investigation suggests that Mn(III) additive essential for promoting SET reduction imine material preventing formation over-reduced amine side product.

Language: Английский

Citations

0

Designing Peptide-Based Nucleophilic Catalysts Possessing Multiple Identical Active Sites for Late-Stage Chlorination of Peptides and Drugs DOI

Subimal Patra,

Haripriyo Mondal,

Uttam Dash

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 3, 2025

In the quest for developing catalysts with multiple active sites, we designed a series of methionine-based peptide prepared by classical coupling. Given widespread presence aromatic chloro-substituents and their significant pharmacokinetic properties, performance these were evaluated late-stage chlorination tyrosine residue on peptides up to octamer as well drug molecules. The operationally simple reaction conditions, excellent catalyst loading 0.25 mol %, gram-scale reactions are major highlights this method.

Language: Английский

Citations

0

Photoinduced pinacol coupling of carbon-carbon bonds via triethoxysilane or Hantzsch Ester DOI
Jianhua Liu,

Gelan Wang,

Chen Chen

et al.

Molecular Catalysis, Journal Year: 2025, Volume and Issue: 579, P. 115088 - 115088

Published: April 5, 2025

Language: Английский

Citations

0

Reductive photoredox transformations of carbonyl derivatives enabled by strongly reducing photosensitizers DOI Creative Commons
Vinh Q. Dang, Thomas S. Teets

Chemical Science, Journal Year: 2023, Volume and Issue: 14(35), P. 9526 - 9532

Published: Jan. 1, 2023

Visible-light photoredox catalysis is well-established as a powerful and versatile organic synthesis strategy. However, some substrate classes, despite being attractive precursors, are recalcitrant to single-electron redox chemistry thus not very amenable approaches. Among these carbonyl derivatives, e.g. ketones, aldehydes, imines, which in most cases require Lewis or Brønsted acidic additives activate via photoinduced electron transfer. In this work, we unveil range of transformations on ketones enabled by strongly reducing photosensitizers operating under simple, general conditions with single sacrificial reductant no additives. Specific reactions described here umpolung C-C bond forming between aromatic imines electron-poor alkenes, imino-pinacol homocoupling challenging alkyl-aryl imine substrates, γ-lactonization methyl acrylate. The all initiated transfer form ketyl iminyl that subsequently trapped.

Language: Английский

Citations

6

Photoredox‐Catalyzed Generation of Tertiary Anions from Primary Amines via a Radical Polar Crossover DOI
Austin D. Marchese, Julia R. Dorsheimer, Tomislav Rovis

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(6)

Published: Jan. 8, 2024

Abstract A method for the generation of tertiary carbanions via a deaminative radical‐polar crossover is reported using redox active imines from α‐tertiary primary amines. variety benzylic amines and amino esters can be used in this approach, with latter engaging novel “aza‐Reformatsky” reaction. Electronic trends correlate stability resulting carbanion reaction efficiency. The anions trapped different electrophiles including aldehydes, ketones, imines, Michael acceptors, H 2 O/D O. Selective anion formation achieved presence another equivalent or more acidic C−H bond both an inter‐ intramolecular fashion. Mechanistic studies suggest intermediacy discrete intermediate.

Language: Английский

Citations

1

Catalytic Cycloisomerization of Enyne Diesters Derived from Biaryls and Related Substrates DOI
Manoj Saini,

Karmdeo Prajapati,

Rashi Sharma

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(13), P. 2211 - 2217

Published: June 10, 2023

Abstract Enyne diesters derived from biaryls and related substrates undergo intramolecular [2+2]‐cycloaddition concomitant cyclo‐reversion when treated with 10 mol% In(OTf) 3 in 1,2‐dichloroethane. This enyne metathesis type cycloisomerization reaction enables the synthesis of phenanthrene, benzophenanthrene, benzotetraphene other polycyclic (hetero)aromatic compounds bearing a synthetically useful diethyl β‐(hetero)arylidene malonate moiety step‐ atom‐economic manner. ‐catalyzed two independent on 5 b provides direct access to benzotetraphenes 6 containing bis(diethyl β‐phenylmethylene malonate) moiety. Tetrasubstituted vinylidene 4 , substiututed by different aromatic groups, is stereoselectively converted into E ‐ Z ‐isomer triaryl group all carbon tetrasubstituted olefins ( 8 a′ ) via Pd‐catalyzed stereoselective decarboxylative arylation reaction.

Language: Английский

Citations

3

Visible‐Light‐Mediated Synthesis of Aryl Ketones and Aldehydes from N‐(acyloxy)phthalimides Esters DOI

Di Ding,

Ruiying Wan,

Yuchen Qi

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(4)

Published: Jan. 16, 2024

Abstract A visible‐light‐mediated decarboxylative oxidation of benzylic redox active esters is described. diverse array aromatic ketones or aldehydes could be achieved (15 examples) from secondary primary aliphatic carboxylic acids. mechanism involving resonance transformation in the presence Cs 2 CO 3 proposed.

Language: Английский

Citations

0

Pyrene-Based Organic Photoredox Catalysts for Carbon–Carbon Bond-Forming Reactions: Reductive Coupling of Aromatic Carbonyl and Imine Compounds DOI
Shusuke Okamoto, Daisuke Nagai

Organic Letters, Journal Year: 2024, Volume and Issue: 26(36), P. 7718 - 7722

Published: Sept. 5, 2024

Metal-free photoredox catalysts built upon a pyrene core were developed for carbon-carbon bond-forming reactions. Among these catalysts, derivative containing urea moiety effectively facilitated the reductive coupling of aromatic carbonyl and imine compounds under blue LED irradiation. This process provided corresponding vicinal diols diamines in good yields.

Language: Английский

Citations

0

Amidoboronates: bringing together the synthesis of BN-heterocyclesviaa reductive coupling and dynamic covalent chemistry DOI Creative Commons
Anna J. McConnell

Dalton Transactions, Journal Year: 2023, Volume and Issue: 52(27), P. 9189 - 9201

Published: Jan. 1, 2023

This Perspective discusses the synthesis of amidoboronates and dynamic covalent chemistry C–C, B–N B–O bonds.

Language: Английский

Citations

1

Semiconductor Quantum Dots Act as Photocatalysts for Carbon–Carbon Bond Formation: Selective Functionalization of Xanthene’s 9H Position DOI

Jiteshkumar P. Deore,

Mrinmoy De

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(23), P. 16292 - 16301

Published: Nov. 18, 2023

The potential of CdSe, CdS, MoS2, and WS2 QDs as semiconductor photocatalysts for selective functionalization the xanthene 9H position through carbon-carbon bond formation has been investigated. Our study reveals valuable insights into energy-transfer electron-transfer pathways involved in these reactions, well radical polar crossover (RPC) triplet-to-triplet energy transfer (TTEnT) processes. Notably, this approach offers a range intriguing features, including visible-light-mediated processes, inexpensive catalytic systems, mild reaction conditions, broad substrate scope, unfunctionalized starting materials, suitability gram-scale synthesis. This makes significant contribution to newly emerging field QD-catalyzed paving way future explorations.

Language: Английский

Citations

1