4.7 Article

Organoboron/iodide-catalyzed photoredox N-functionalization of NH-sulfoximines/sulfonimidamides

相关参考文献

注意:仅列出部分参考文献,下载原文获取全部文献信息。
Article Chemistry, Multidisciplinary

Photocatalytic Metal Hydride Hydrogen Atom Transfer Mediated Allene Functionalization by Cobalt and Titanium Dual Catalysis

Huaipu Yan et al.

Summary: Co-porphines were discovered to be highly efficient MHAT catalysts for chemoselective allene functionalization under photoirradiation with a loading of only 0.01 mol %. The combination of photo Co-MHAT and Ti catalysis enabled successful carbonyl allylation, providing expedient access to beta-functionalized homoallylic alcohols in over 100 examples with exceptional regio- and diastereoselectivity. Mechanism studies supported the key role of selectively transferring hydrogen atoms from cobalt hydride to allenes and generating allyl radicals in the catalytic cycle.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

Article Chemistry, Organic

Three-Component Oxychalcogenation of Alkenes under Metal-Free Conditions: A Tetrabutylammonium Tribromide-Catalyzed System

Jiawei Huang et al.

Summary: A three-component oxychalcogenation reaction is achieved in this study, using alkenes, diselenides/thiophenols, and H2O/alcohols as reactants. Tetrabutylammonium tribromide (TBATB) and dimethylsulfoxide (DMSO) are employed as the catalyst and terminal oxidant, respectively, enabling the difunctionalization transformation. This metal-free reaction system shows excellent functional group compatibility and provides a unified and practical approach to access beta-hydroxyl or beta-alkoxy organochalcogenides.

JOURNAL OF ORGANIC CHEMISTRY (2023)

Article Chemistry, Organic

Visible-Light-Photocatalyzed Dicarbofunctionalization of Conjugated Alkenes with Ketone-Based Dihydroquinazolinones

Pinku Prasad Mondal et al.

Summary: This study describes a visible-light-photocatalyzed 1,2-arylalkylation of N-(arylsulfonyl)acrylamides with ketone-based dihydroquinazolinones. The method unifies the formal C-C bond cleavage of aliphatic ketones with tandem radical alkylation/1,4-aryl migration/desulfonylation to form two different types of vicinal C-C bonds and construct an all-carbon quaternary alpha-stereocenter. It not only enhances the carbogenic complexity but also tolerates diverse functionalities.

ORGANIC LETTERS (2023)

Letter Chemistry, Organic

Semi-Synthesis of (+)-Digitoxigenin from Androstenedione

Linlin Wei et al.

Summary: An efficient stereoselective semi-synthesis of (+)-digitoxigenin with an overall yield of 20.4% has been achieved by a nine-step sequence. Key features of the synthesis include a Saegusa-Ito oxidation reaction, a direct C14 beta-hydroxylation, and a Stille cross-coupling.

SYNLETT (2023)

Article Chemistry, Organic

Electrochemical Decarboxylation Coupling of α-Keto Acids with Thiophenols: A New Avenue for the Synthesis of Thioesters

Huang Jiawei et al.

Summary: Thioester compounds have diverse reactivities and are widely used in the synthesis of bioactive chemicals, natural products, and organic materials. In recent years, decarboxylation coupling reactions between alpha-keto acids and thiols/thiophenols have been employed to access thioesters. This study establishes an electrochemical decarboxylation coupling method using alpha-keto acids and thiophenols as starting materials, leading to moderate to good yields of thioesters. This protocol offers a new, mild, and environmentally friendly route to synthesizing thioester compounds without the need for metal-based catalysts, bases, or external oxidants.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2023)

Article Chemistry, Organic

A nickel/organoboron catalyzed metallaphotoredox platform for C(sp2)-P and C(sp2)-S bond construction

Yuan Zhu et al.

Summary: In this study, a collaborative approach using AQDAB as an organoboron photocatalyst and nickel catalyst in metallaphotoredox catalyzed reactions has been developed to achieve efficient C(sp(2))-P and C(sp(2))-S cross-coupling. The strategy enables the coupling of aryl halides with diarylphosphine oxides and thiols at room temperature under an air atmosphere, leading to the synthesis of triarylphosphine oxides and thioethers in generally moderate to good yields.

ORGANIC CHEMISTRY FRONTIERS (2022)

Article Chemistry, Organic

K2S2O8/I2-Promoted Electrophilic Selenylative Cyclization To Access Seleno-Benzo[b]azepines

Zhen Zhang et al.

Summary: A novel and simple organoselenium-involved 7-membered cyclization method has been developed for accessing diverse seleno-benzo[b]azepines. The protocol involves an electrophilic cyclization process and is conducted under mild conditions. Mechanistic discussions rationalize the observed regioselectivity in the transformation. Further studies on the transformation of seleno-benzo[b]azepines and large-scale experiments demonstrate promising utility of this methodology.

ORGANIC LETTERS (2022)

Article Chemistry, Multidisciplinary

Mechanochemical Solvent-Free N-Sulfenylations of Sulfoximines and Sulfonimidamides

Deshen Kong et al.

Summary: Mechanochemical N-sulfenylations of sulfoximines and sulfonimidamides mediated by silver oxide under solvent-free conditions have been developed. The reactions are easy to perform, proceed well on a gram scale, and tolerate a wide range of functional groups in the substrates. Compared to its solvent-based counterpart, the mechanochemical approach shows significant ecological advantages.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2022)

Review Chemistry, Multidisciplinary

New Opportunities for the Utilization of the Sulfoximine Group in Medicinal Chemistry from the Drug Designer's Perspective

Ulrich Luecking

Summary: This article highlights the emerging trends and opportunities for drug designers to utilize the sulfoximine group in medicinal chemistry, such as in the construction of complex molecules, PROTACs, ADCs, and novel warheads for covalent inhibition. Despite the increasing interest in the sulfoximine group in recent years, there is still ample room for further innovative applications.

CHEMISTRY-A EUROPEAN JOURNAL (2022)

Article Chemistry, Organic

Synthesis of β-Arylseleno Sulfoximines: A Metal-Free Three-Component Reaction Mediated by Tetrabutylammonium Tribromide

Xiaoman Li et al.

Summary: In this study, a tetrabutylammonium tribromide-mediated three-component reaction of alkenes, diselenides, and sulfoximines was established, providing a direct and metal-free access to diverse beta-arylseleno sulfoximine derivatives. This regioselective sulfoximido-selenization protocol proceeds efficiently under mild and ambient conditions with generally good yields. The strategy is characterized by step and atom economy, practicability, a broad substrate scope, and gram-scale synthesis.

JOURNAL OF ORGANIC CHEMISTRY (2022)

Review Chemistry, Medicinal

Application of sulfoximines in medicinal chemistry from 2013 to 2020

Yu Han et al.

Summary: Interest in sulfoximine chemistry has increased in recent years, with several sulfoximine-containing drugs entering clinical trials. However, limited experience in physicochemical and in vitro parameters of sulfoximines hampers their routine application in drug discovery. This review aims to provide support for the addition of sulfoximine components in medicinal chemists' toolbox.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Visible-light-mediated organoboron-catalysed metal-free dehydrogenation of N-heterocycles using molecular oxygen

Lanfeng Wei et al.

Summary: This research explores a visible-light-induced oxidative dehydrogenative process using an organoboron compound as the photocatalyst and molecular oxygen as the sole oxidant. This approach successfully accessed an array of N-heterocycles under metal-free mild conditions, in good to excellent yields.

GREEN CHEMISTRY (2021)

Review Chemistry, Organic

Recent advances in visible-light photocatalytic deuteration reactions

Rong Zhou et al.

Summary: Deuterated organic compounds are widely used in various fields such as medicinal chemistry, mechanistic studies, and quantitative analyses. Photocatalytic deuteration has emerged as a reliable platform for generating deuterated organic molecules, particularly pharmaceutical compounds, with advantages such as mild conditions and good site selectivity. This review summarizes recent advances in visible-light photocatalytic deuteration reactions based on the type of bond deuterated.

ORGANIC CHEMISTRY FRONTIERS (2021)

Article Nanoscience & Nanotechnology

Visible-light photocatalysts: Prospects and challenges

Aleksandra B. Djurisic et al.

APL MATERIALS (2020)

Review Multidisciplinary Sciences

ORGANIC CHEMISTRY Copper's rapid ascent in visible-light photoredox catalysis

Asik Hossain et al.

SCIENCE (2019)

Review Chemistry, Medicinal

Role of sulphur-heterocycles in medicinal chemistry: An update

Shelly Pathania et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2019)

Review Chemistry, Applied

Progress in Difluoroalkylation of Organic Substrates by Visible Light Photoredox Catalysis

Agostinho Lemos et al.

ADVANCED SYNTHESIS & CATALYSIS (2019)

Article Chemistry, Organic

I2-Catalyzed Oxidative N-P Cross-Coupling of Diarylphosphine Oxides and Sulfoximines

Mingchao Tan et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2019)

Article Chemistry, Organic

Copper-promoted dehydrogenative cross-coupling reaction of dialkyl phosphites with sulfoximines

Surabhi Gupta et al.

ORGANIC CHEMISTRY FRONTIERS (2019)

Article Chemistry, Multidisciplinary

Direct Synthesis of Polysubstituted Aldehydes via Visible-Light Catalysis

Fengjin Wu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Organic

A One-Pot Cascade Reaction by Combining NH-Sulfoximines with Thiophenols Under Mild Conditions

Yao Peng et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2018)

Article Chemistry, Applied

Polycyclic Sulfoximines as New Scaffolds for Drug Discovery

Mark L. G. Borst et al.

ACS COMBINATORIAL SCIENCE (2018)

Article Chemistry, Multidisciplinary

Green and Efficient Synthesis of N-Sulfenyl Sulfoximines in Water

Yan Lin et al.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2018)

Article Biochemical Research Methods

Preparation of visible-light-activated metal complexes and their use in photoredox/nickel dual catalysis

Christopher B. Kelly et al.

NATURE PROTOCOLS (2017)

Review Chemistry, Multidisciplinary

Visible light-induced transition metal-catalyzed transformations: beyond conventional photosensitizers

Marvin Parasram et al.

CHEMICAL SOCIETY REVIEWS (2017)

Article Chemistry, Multidisciplinary

Visible-Light Photocatalytic Intramolecular Cyclopropane Ring Expansion

Javier Luis-Barrera et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Review Chemistry, Multidisciplinary

Sulfonimidamides in Medicinal and Agricultural Chemistry

Praveen K. Chinthakindi et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Review Chemistry, Applied

Recent Advances in Organic Reactions Involving Elemental Sulfur

Thanh Binh Nguyen

ADVANCED SYNTHESIS & CATALYSIS (2017)

Article Chemistry, Multidisciplinary

Copper-catalyzed N-thioetherification of sulfoximines using disulfides

Hui Zhu et al.

CHEMICAL COMMUNICATIONS (2016)

Article Chemistry, Applied

A Single-Stage, Continuous High-Efficiency Extraction Device (HEED) for Flow Synthesis

Craig Day et al.

ORGANIC PROCESS RESEARCH & DEVELOPMENT (2016)

Article Chemistry, Multidisciplinary

Visible-Light Photoredox-Catalyzed Semipinacol-Type Rearrangement: Trifluoromethylation/Ring Expansion by a Radical-Polar Mechanism

Basudev Sahoo et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Organic

Regioselective, Molecular Iodine-Mediated C3 Iodination of Quinolines

Kai Sun et al.

ORGANIC LETTERS (2015)

Article Chemistry, Multidisciplinary

Sulfoximines: A Neglected Opportunity in Medicinal Chemistry

Ulrich Luecking

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)