scholarly journals Recent Advances in the Selective Oxidative Dearomatization of Phenols to o-Quinones and o-Quinols with Hypervalent Iodine Reagents

Synlett ◽  
2021 ◽  
Author(s):  
Sarah E. Wengryniuk ◽  
Xiao Xiao
Keyword(s):  
Coordination Chemistry ◽  
Organic Synthesis ◽  
Phenol Oxidation ◽  
Hypervalent Iodine ◽  
Direct Oxidation ◽  
Oxidative Dearomatization ◽  
Total Syntheses ◽  
Recent Advances

Abstract ortho-Quinones are valuable molecular frameworks with diverse applications across biology, materials, organic synthesis, catalysis, and coordination chemistry. Despite their broad utility, their synthesis remains challenging, in particular via the direct oxidation of readily accessible phenols, due to the need to affect regioselective ortho oxidation coupled with the sensitivity of the resulting o-quinone products. The perspective looks at the emergence of I(V) hypervalent iodine reagents as an effective class of oxidants for regioselective o-quinone synthesis. The application of these reagents in regioselective phenol oxidation to both o-quinones and o-quinols will be discussed, including a recent report from our laboratory on the first method for the oxidation of electron-deficient phenols using a novel nitrogen-ligated I(V) reagent. Also included are select examples of total syntheses utilizing this methodology as well as recent advancements in chiral I(V) reagent design for asymmetric phenol dearomatization.1 Introduction2 I(V): Hypervalent Iodine Reagents3 I(V)-Mediated Dearomatization to o-Quinones4 Bisnitrogen-Ligated I(V) Reagents: ortho Dearomatization of Electron-Poor Phenols5 I(V)-Mediated Dearomatization to o-Quinols6 Conclusion and Outlook

scholarly journals Recent Advances in the Application of in-situ Generated Hypervalent Iodine Reagents in Organic Synthesis

2020 ◽  
Vol 40 (1) ◽  
pp. 28 ◽  
Author(s):  
Liu Yang ◽  
Guohe Xu ◽  
Jingjun Ma ◽  
Qian Yang ◽  
An Feng ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Hypervalent Iodine ◽  
Recent Advances

Recent Advances in P2O5 Catalyzed Organic Synthesis

2012 ◽  
Vol 1 (3) ◽  
pp. 155-163 ◽  
Author(s):  
Maya Shankar Singh
Keyword(s):  
Organic Synthesis ◽  
Recent Advances

Recent advances in the Silver catalysed synthesis of furan and its applications

2020 ◽  
Vol 09 ◽  
Author(s):  
C M A Afsina ◽  
Mohan Neetha ◽  
Thaipparambil Aneeja ◽  
Gopinathan Anilkumar
Keyword(s):  
Organic Synthesis ◽  
Oxidation Potential ◽  
Silver Complexes ◽  
Wide Spread ◽  
Silver Catalysts ◽  
Recent Advances ◽  
High Oxidation ◽  
Furan Moiety ◽  
Anti Fungal ◽  
Fragrance Compounds

: Furan and its derivatives find wide-spread application as pharmaceuticals, pigments, dyes, brighteners, flavour & fragrance compounds and insecticides. They also exhibit anti-hyperglycemic, analgesic, anti-inflammatory, antibacterial, anti-fungal and anti-tumour activities. Silver catalysts are nowadays commonly used in organic synthesis due to the high oxidation potential and versatile nature of silver complexes. In this review, we summarise the recent advances in the synthesis and applications of furan moiety using silver catalysis and covers literature from 2015-2020.

Ligand-Driven Advances in Iridium Catalyzed sp3 C-H Borylation: 2,2’-Dipyridylarylmethane

Synlett ◽  
2020 ◽  
Author(s):  
Margaret R Jones ◽  
Nathan D. Schley
Keyword(s):  
Recent Work ◽  
Organic Synthesis ◽  
Functional Group ◽  
Reaction Conditions ◽  
Recent Advances ◽  
Additional Ligand ◽  
Limited Application ◽  
Hydrocarbon Substrates ◽  
Phenanthroline Ligands

The field of catalytic C-H borylation has grown considerably since its founding, providing a means for the preparation of synthetically versatile organoborane products. While sp2 C-H borylation methods have found widespread and practical use in organic synthesis, the analogous sp3 C-H borylation reaction remains challenging and has seen limited application. Existing catalysts are often hindered by incomplete consumption of the diboron reagent, poor functional group tolerance, harsh reaction conditions, and the need for excess or neat substrate. These challenges acutely affect C-H borylation chemistry of unactivated hydrocarbon substrates, which has lagged in comparison to methods for the C-H borylation of activated compounds. Herein we discuss recent advances in sp3 C-H borylation of undirected substrates in the context of two particular challenges: (1) utilization of the diboron reagent and (2) the need for excess or neat substrate. Our recent work on the application of dipyridylarylmethane ligands in sp3 C-H borylation has allowed us to make contributions in this space and has presented an additional ligand scaffold to supplement traditional phenanthroline ligands.

Recent Advances in C–Br Bond Formation

Synlett ◽  
2021 ◽  
Author(s):  
Ying-Yeung Yeung ◽  
Jonathan Wong
Keyword(s):  
Organic Synthesis ◽  
Aromatic Compounds ◽  
Bond Formation ◽  
Cross Coupling ◽  
Catalytic Site ◽  
Atom Transfer ◽  
Bond Forming ◽  
Recent Advances ◽  
Catalytic Asymmetric ◽  
Site Selective

AbstractOrganobromine compounds are extremely useful in organic synthesis. In this perspective, a focused discussion on some recent advancements in C–Br bond-forming reactions is presented.1 Introduction2 Selected Recent Advances2.1 Catalytic Asymmetric Bromopolycyclization of Olefinic Substrates2.2 Catalytic Asymmetric Intermolecular Bromination2.3 Some New Catalysts and Reagents for Bromination2.4 Catalytic Site-Selective Bromination of Aromatic Compounds2.5 sp3 C–H Bromination via Atom Transfer/Cross-Coupling3 Outlook

Recent advances in the synthesis and reactivity of azetidines: strain-driven character of the four-membered heterocycle

2021 ◽  
Vol 19 (15) ◽  
pp. 3274-3286
Author(s):  
Haseeb Mughal ◽  
Michal Szostak
Keyword(s):  
Organic Synthesis ◽  
Future Directions ◽  
Recent Advances ◽  
Membered Heterocycle

Azetidines represent one of the most important four-membered heterocycles in organic synthesis. We provide an overview of the synthesis, reactivity and application of azetidines with a focus on the most recent advances, trends and future directions.

scholarly journals Sulfur-based chiral iodoarenes: An underexplored class of chiral hypervalent iodine reagents

Synthesis ◽  
2021 ◽  
Author(s):  
Mohamed Elsherbini ◽  
Arnaud Osi ◽  
Haifa Alharbi ◽  
Fatemah Karam ◽  
Thomas Wirth
Keyword(s):  
Organic Synthesis ◽  
Hypervalent Iodine

Chiral hypervalent iodine reagents are active players in modern stereoselective organic synthesis. Structurally diverse chiral hypervalent iodine reagents have been synthesised and extensively studied, but hypervalent iodine reagents containing chiral sulfur stereogenic centre are scarce and their synthesis is challenging. A small library of iodoarenes containing chiral sulfinamide and chiral sulfoximine moieties has been synthesised using commercially available reagents. The oxidation of the chiral iodoarene precursors to iodine(III) reagents was cumbersome due to facile overoxidation of the sulfoxide moiety and hence loss of chirality under various oxidation conditions. Oxidation of chiral sulfonimidoyl derivatives to the corresponding hypervalent iodine reagents was successful and led to novel sulfur-based chiral iodine(III) reagents.

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