☆ 4.8 Article

Photocatalytic synthesis of 2,3-diamines from anilines and DIPEA via C-N bond cleavage and C-C bond formation

GREEN CHEMISTRY (2024)

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

One-Pot Synthesis of Sulfonamides from Unactivated Acids and Amines via Aromatic Decarboxylative Halosulfonylation

P. Scott Pedersen et al.

Summary: In this study, a new synthetic method was reported to form sulfonamides, important amide bioisosteres, by coupling carboxylic acids and amines. This method utilizes copper ligand-to-metal charge transfer (LMCT) to convert aromatic acids to sulfonyl chlorides, followed by one-pot amination to form the corresponding sulfonamide. The method can be applied to a diverse set of substrates and also enables the synthesis of (hetero)aryl sulfonyl fluorides, which have utility in chemical probes and programmable bifunctional reagents.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2023)

添加到收藏夹

Article Multidisciplinary Sciences

Decarboxylation of β-boryl NHPI esters enables radical 1,2-boron shift for the assembly of versatile organoborons

Yu Guo et al.

Summary: In recent years, there have been extensive studies on 1,2-R shifts based on tetra-coordinate boron species. However, the corresponding radical migrations for the construction of organoborons are still in the early stages. By developing a new synthetic method, efficient and alternative strategies can be obtained to enrich these underdeveloped radical boron migrations.

NATURE COMMUNICATIONS (2023)

添加到收藏夹

Review Chemistry, Multidisciplinary

Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis

Nicholas E. S. Tay et al.

Summary: Redox processes play a crucial role in synthetic methods involving electrochemistry and photoredox catalysis. Both approaches offer access to high energy intermediates that allow for unconventional bond formations. However, while they provide similar intermediates, electrochemistry and photoredox catalysis differ in their physical chemistry principles. Understanding these differences is essential for designing new transformations and bond disconnections.

CHEMICAL REVIEWS (2022)

添加到收藏夹

Article Chemistry, Organic

Photoredox-Catalyzed Synthesis of α-Amino Acid Amides by Imine Carbamoylation

Luana Cardinale et al.

Summary: The study presents a straightforward protocol for the photocatalytic carbamoylation of imines using easily accessible and stable 4-amido Hantzsch ester derivatives as precursors to carbamoyl radicals. The reaction occurs under blue light irradiation in the presence of the photocatalyst 3DPAFIPN and acid additives, with mechanistic studies suggesting a photoredox mechanism involving carbamoyl radicals.

ORGANIC LETTERS (2022)

添加到收藏夹

Review Biochemistry & Molecular Biology

N-Dealkylation of Amines

Ali Alipour Najmi et al.

Summary: N-dealkylation is an important chemical transformation for the synthesis of pharmaceuticals and chemicals, as well as a crucial metabolic pathway in vivo. The identification and synthesis of drug metabolites has significant implications in drug development studies.

MOLECULES (2022)

添加到收藏夹

Article Chemistry, Organic

Deaminative Cyclization of Tertiary Amines for the Synthesis of 2-Arylquinoline Derivatives with a Nonsubstituted Vinylene Fragment

Qinghe Gao et al.

Summary: By using triethylamine as a vinylene source, a convenient protocol for the regioselective synthesis of beta,gamma-nonsubstituted 2-arylquinolines from aldehydes and arylamines has been developed. The deaminative cyclization can also be extended to long-chain tertiary alkylamines, allowing diverse alkyl groups to be simultaneously introduced into the pyridine rings. This process demonstrates a new conversion pathway for simultaneous dual C(sp(3))-H bond functionalization of tertiary amines, in which the transient acyclic enamines generated in situ undergo the Povarov reaction.

ORGANIC LETTERS (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Metal-Free Visible-Light-Induced Atom-Transfer Radical Addition Reaction of Alkenes/Alkynes with ICH2CN

Chunxiang Pan et al.

Summary: New blue-light promoted methods for the addition of iodoacetonitrile to alkene/alkynes have been developed. Different products can be obtained under different substrate conditions. A plausible reaction mechanism is proposed.

CHINESE JOURNAL OF CHEMISTRY (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Reinterpreting the Fate of Iridium(III) Photocatalysts-Screening a Combinatorial Library to Explore Light-Driven Side-Reactions

Joseph C. Bawden et al.

Summary: In this work, the scope of a previously demonstrated side reaction in heteroleptic iridium(III) complexes was explored using high throughput synthesis and screening under photochemical conditions. The compositions of the ancillary ligands were found to be crucial in determining the different chemical pathways and the photochemical stability of the complexes.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Article Chemistry, Physical

Energy transfer-enabled unsymmetrical diamination using bifunctional nitrogen-radical precursors

Guangying Tan et al.

Summary: This study reveals a metal-free, photosensitized dearomative unsymmetrical diamination reaction, which generates two N-centred radicals with different reactivity via an energy transfer process, achieving the highly selective synthesis of vicinal diamines.

NATURE CATALYSIS (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Regioselective Access to Vicinal Diamines by Metal-Free Photosensitized Amidylimination of Alkenes with Oxime Esters

Yu Zheng et al.

Summary: A metal-free photosensitized protocol for regioselective diamination of alkene feedstocks was developed. The reaction proceeds in a single step and yields differentially protected 1,2-diamines in moderate to high yields. Mechanistic studies reveal that the excellent regioselectivity is due to the large reactivity difference between two different N-centered radical species.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Photoinduced Radical Relay Way Toward α-CF3 Ketones with Low-Cost Trifluoromethylation Reagents

Huamin Wang et al.

Summary: This study presents a cost-efficient approach for the synthesis of α-CF3 ketones using trifluoromethyl reagents under metal-free and redox-neutral conditions. The potential application of this method for late-stage modification of drug segments and gram-scale synthesis was highlighted. Mechanistic studies indicated that the transformation might involve a radical process and acetic acid played a crucial role in promoting the formation of enol triflates and accelerating the conversion to α-CF3 ketones.

CCS CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Divergent Aminocarbonylations of Alkynes Enabled by Photoredox/Nickel Dual Catalysis

Xian Zhao et al.

Summary: A metallaphotoredox-catalyzed strategy for the aminocarbonylation of alkynes with amines and CO has been developed. This method allows for selective synthesis of alpha,beta-unsaturated amides and a sequential four-component hydroaminocarbonylation/radical alkylation, demonstrating great potential in the selective and divergent functionalization of alkynes. Preliminary mechanistic studies suggest a photoinduced oxidative insertion of aniline and CO into nickel followed by a migratory insertion of (carbamoyl)nickel species may be involved.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Minimization of Back-Electron Transfer Enables the Elusive sp3 C-H Functionalization of Secondary Anilines

Huaibo Zhao et al.

Summary: The presence of an exogenous alkylamine in photoredox catalysis can minimize back-electron transfer in anilines and facilitate the generation of alpha-anilinoalkyl radicals, enabling divergent sp(3) C-H functionalization.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

添加到收藏夹

Article Chemistry, Organic

Nanosized CdS as a Reusable Photocatalyst: The Study of Different Reaction Pathways between Tertiary Amines and Aryl Sulfonyl Chlorides through Visible-Light-Induced N-Dealkylation and C-H Activation Processes

Somayeh Firoozi et al.

Summary: The reaction of sulfonyl chlorides and tertiary amines catalyzed by cadmium sulfide nanoparticles under visible light irradiation results in different products depending on reaction conditions, including secondary amines and various sulfonyl compounds. The use of visible light as a renewable energy source in these reactions is cost-effective and efficient.

JOURNAL OF ORGANIC CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Late-Stage N-Me Selective Arylation of Trialkylamines Enabled by Ni/Photoredox Dual Catalysis

Yangyang Shen et al.

Summary: This study demonstrates the site-selective alpha-arylation of various trialkylamines using a nickel/photoredox dual catalysis strategy, showing exclusive N-Me selectivity even in the context of late-stage arylation of pharmaceutical compounds. Mechanistic studies reveal the unconventional behavior of the Ni catalyst in intercepting the alpha-amino radicals.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Diastereodivergent Intermolecular 1,2-Diamination of Unactivated Alkenes Enabled by Iodine Catalysis

Satoshi Minakata et al.

Summary: This study demonstrates the stereospecific, substrate-controlled intermolecular anti- and syn-1,2-diaminations of unactivated alkenes using an iodine catalyst. The combined use of the two methods allows access to all diastereomeric forms of 1,2-diamines, even in the presence of E- and Z-alkenes, with the resulting products easily convertible into free vicinal diamines.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

添加到收藏夹

Article Chemistry, Organic

Regioselective Three-Component Synthesis of Vicinal Diamines via 1,2-Diamination of Styrenes

Jie Cao et al.

Summary: The vicinal diamine motif is important in natural products, drug design, and organic synthesis, and developing methods for synthesizing vicinal diamines has long been of interest. This study reports on a regioselective intermolecular three-component vicinal diamination reaction using styrenes, acetonitrile, and azodicarboxylates. The diamination products can be obtained in moderate to excellent yields via the Ritter reaction, and synthetic applications and theoretical studies of this reaction have been conducted.

ORGANIC LETTERS (2021)

添加到收藏夹

Article Chemistry, Organic

CBZ6 as a Recyclable Organic Photoreductant for Pinacol Coupling

Hua Wang et al.

Summary: The recyclable organic photoreductant CBZ6 catalyzes the reductive coupling of aldehydes, ketones, and imines under purple light irradiation, producing 1,2-diols and 1,2-diamines. With a high oxidation potential, CBZ6 is suitable for the reductive coupling of carbonyl compounds and their derivatives, making it a promising candidate for large-scale photoreductive synthesis.

ORGANIC LETTERS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Catalytic Diastereo- and Enantioconvergent Synthesis of Vicinal Diamines from Diols through Borrowing Hydrogen

Hui-Jie Pan et al.

Summary: This study presents an unprecedented diastereoconvergent synthesis of vicinal diamines from diols, using an economical and redox-neutral process. Efficient and diastereoselective coupling of readily available anilines and 1,2-diols under cooperative ruthenium and Lewis acid catalysis was achieved, along with the first enantioconvergent double amination of racemic 1,2-diols through an effective chiral iridium/phosphoric acid co-catalyzed procedure, leading to practical access to highly valuable enantioenriched vicinal diamines.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

添加到收藏夹

Article Chemistry, Physical

Reductive imino-pinacol coupling reaction of halogenated aromatic imines and iminium ions catalyzed by precious metal catalysts using hydrogen

K. N. R. Dumoleijn et al.

Summary: The study reported a heterogeneously catalyzed process for the reductive coupling of imines and iminium ions using precious metal catalysts and hydrogen gas. The optimized method allowed the production of aromatic vicinal diamines and unraveled the most important mechanistic features of the reaction. The developed methodology is highly efficient for the coupling of aromatic iminium ions.

JOURNAL OF CATALYSIS (2021)

添加到收藏夹

Article Chemistry, Organic

Synthesis of pentafluorobenzene-based NHC adducts and their catalytic activity in the microwave-assisted reactions of aldehydes

Evanthia Papadaki et al.

TETRAHEDRON LETTERS (2020)

添加到收藏夹

Article Chemistry, Organic

Formation of Enamines via Catalytic Dehydrogenation by Pincer-Iridium Complexes

Yansong J. Lu et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantioselective Reductive Coupling of Imines Templated by Chiral Diboron

Mingkang Zhou et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

添加到收藏夹

Article Electrochemistry

Reductive Coupling of Aromatic Aldehydes and Ketones Under Electrochemical Conditions

Toreshettahally R. Swaroop et al.

JOURNAL OF THE ELECTROCHEMICAL SOCIETY (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Photocatalyst-free visible light promoted E → Z isomerization of alkenes

Jianbin Xu et al.

GREEN CHEMISTRY (2020)

添加到收藏夹

Article Chemistry, Physical

Photoinduced Copper-Catalyzed Radical Aminocarbonylation of Cycloketone Oxime Esters

Bin Lu et al.

ACS CATALYSIS (2019)

添加到收藏夹

Review Chemistry, Multidisciplinary

Reductive Amination in the Synthesis of Pharmaceuticals

Oleg Afanasyev et al.

CHEMICAL REVIEWS (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Photocatalyzed oxidative dehydrogenation of hydrazobenzenes to azobenzenes

Haiping Lv et al.

GREEN CHEMISTRY (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Application of coumarin dyes for organic photoredox catalysis

Andrea Gualandi et al.

CHEMICAL COMMUNICATIONS (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Organic synthesis provides opportunities to transform drug discovery

David C. Blakemore et al.

NATURE CHEMISTRY (2018)

添加到收藏夹

Article Chemistry, Organic

Aminative Umpolung cyclization for synthesis of chiral exocyclic vicinal diamines

Feng Liu et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Synthesis of Chiral Vicinal Diamines by Silver(I)-Catalyzed Enantioselective Aminolysis of N-Tosylaziridines

Zhuo Chai et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

添加到收藏夹

Article Chemistry, Organic

A Metal-Free Approach to 1,2-Diamines via Visible Light-Driven Reductive Coupling of 'mines with Perylene as a Photoredox Catalyst

Shusuke Okamoto et al.

JOURNAL OF ORGANIC CHEMISTRY (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

NHC Ligands Tailored for Simultaneous Regio- and Enantiocontrol in Nickel-Catalyzed Reductive Couplings

Hengbin Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Catalytic Asymmetric Diamination of Styrenes

Kilian Muniz et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

添加到收藏夹

Article Chemistry, Organic

Photoredox-Catalyzed Diamidation and Oxidative Amidation of Alkenes: Solvent-Enabled Synthesis of 1,2-Diamides and α-Amino Ketones

Qixue Qin et al.

ORGANIC LETTERS (2017)

添加到收藏夹

Article Multidisciplinary Sciences

Metal-catalyzed electrochemical diazidation of alkenes

Niankai Fu et al.

SCIENCE (2017)

添加到收藏夹

Article Chemistry, Physical

Diastereofacial π-Stacking as an Approach To Access an Axially Chiral P,N-Ligand for Asymmetric Catalysis

Balaji V. Rokade et al.

ACS CATALYSIS (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Reductive Umpolung of Carbonyl Derivatives with Visible-Light Photoredox Catalysis: Direct Access to Vicinal Diamines and Amino Alcohols via α-Amino Radicals and Ketyl Radicals

Eleonora Fava et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

添加到收藏夹

Article Chemistry, Multidisciplinary

Metal-free reductive coupling of C = O and C = N bonds driven by visible light: use of perylene as a simple photoredox catalyst

Shusuke Okamoto et al.

CHEMICAL COMMUNICATIONS (2016)

添加到收藏夹

Article Chemistry, Multidisciplinary

α-Diamine Nickel Catalysts with Nonplanar Chelate Rings for Ethylene Polymerization

Heng Liao et al.

CHEMISTRY-A EUROPEAN JOURNAL (2016)

添加到收藏夹

Article Chemistry, Organic

A Highly Stereoselective Metal-Free Hydrogenation of Diimines for the Synthesis of Cis-Vicinal Diamines

Xiaxia Zhu et al.

ORGANIC LETTERS (2015)

添加到收藏夹

Article Chemistry, Organic

Diastereoselective imino-pinacol coupling of chiral imines promoted by Mg(0) and a Grignard reagent

Kai Kitajima et al.

TETRAHEDRON (2015)

添加到收藏夹

Article Chemistry, Organic

A novel one-pot synthesis of vicinal diamines with benzaldehyde and aniline derivatives mediated by BiCl3/Zn

Chang-Cheng Wang et al.

TETRAHEDRON LETTERS (2015)

添加到收藏夹

Article Chemistry, Organic

The Ti-BINOLate-catalyzed, enantioselective ring-opening of meso-aziridines with amines

Saravanan Peruncheralathan et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2013)

添加到收藏夹

Article Chemistry, Multidisciplinary

Stereocontrolled Synthesis of Vicinal Diamines by Organocatalytic Asymmetric Mannich Reaction of N-Protected Aminoacetaldehydes: Formal Synthesis of (-)-Agelastatin A

Taichi Kano et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

添加到收藏夹

Article Chemistry, Multidisciplinary

Diastereoselectively Switchable Enantioselective Trapping of Carbamate Ammonium Ylides with Imines

Jun Jiang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

添加到收藏夹

Article Chemistry, Multidisciplinary

A Catalytic Tethering Strategy: Simple Aldehydes Catalyze Intermolecular Alkene Hydroaminations

Melissa J. MacDonald et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

添加到收藏夹

Article Chemistry, Organic

Iron-Catalyzed Ring-Opening of meso-Aziridines with Amines

Alex Marti et al.

SYNLETT (2011)

添加到收藏夹

Article Chemistry, Multidisciplinary

Substrate-Controlled Diastereoselectivity Switch in Catalytic Asymmetric Direct Mannich Reaction of Glycine Derivatives with Imines: From anti- to syn-alpha,beta-Diamino Acids

Jorge Hernandez-Toribio et al.

CHEMISTRY-A EUROPEAN JOURNAL (2010)

添加到收藏夹

Article Chemistry, Organic

Highly Enantio- and Diastereoselective Mannich Reactions of Glycine Schiff Bases with in situ Generated N-Boc-imines Catalyzed by a Cinchona Alkaloid Thiourea

Haile Zhang et al.

ORGANIC LETTERS (2010)

添加到收藏夹

Article Chemistry, Organic

A new Yb3+-catalyzed pinacol and imine-coupling reaction

Helen C. Aspinall et al.

TETRAHEDRON LETTERS (2010)

添加到收藏夹

Article Chemistry, Multidisciplinary

Titanium Binolate Catalyzed Aminolysis of meso Aziridines: A Highly Enantioselective and Direct Access to 1,2-Diamines

Saravanan Peruncheralathan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

添加到收藏夹

Article Chemistry, Multidisciplinary

A N,N '-Dioxide-Copper(II) Complex as an Efficient Catalyst for the Enantioselective and Diastereoselective Mannich-Type Reaction of Glycine Schiff Bases with Aldimines

Deju Shang et al.

CHEMISTRY-A EUROPEAN JOURNAL (2009)

添加到收藏夹

Article Chemistry, Multidisciplinary

Metal-catalysed 1,2-diamination reactions

Francesca Cardona et al.

NATURE CHEMISTRY (2009)

添加到收藏夹

Article Chemistry, Applied

Palladium-Catalyzed N-Demethylation/N-Acylation of Some Morphine and Tropane Alkaloids

Robert J. Carroll et al.

ADVANCED SYNTHESIS & CATALYSIS (2008)

添加到收藏夹

Article Chemistry, Multidisciplinary

Direct Mannich Reaction of Glycinate Schiff Bases with N-(8-Quinolyl)sulfonyl Imines: A Catalytic Asymmetric Approach to anti-α,β-Diamino Esters

Jorge Hernandez-Toribio et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

添加到收藏夹

Article Chemistry, Multidisciplinary

Complete Switch of Product Selectivity in Asymmetric Direct Aldol Reaction with Two Different Chiral Organocatalysts from a Common Chiral Source

Keiji Nakayama et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

添加到收藏夹

Article Chemistry, Multidisciplinary

Highly Diastereoselective Switchable Enantioselective Mannich Reaction of Glycine Derivatives with Imines

Xiao-Xia Yan et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

添加到收藏夹

Article Chemistry, Organic

Scandium triflate catalyzed aminolysis of meso-aziridines

Saravanan Peruncheralathan et al.

SYNLETT (2007)

添加到收藏夹

Article Chemistry, Organic

Direct-type catalytic three-component Mannich reactions leading to an efficient synthesis of α,β-diamino acid derivatives

Matthew M. Salter et al.

ORGANIC LETTERS (2006)

添加到收藏夹

Review Biochemistry & Molecular Biology

Vicinal diamino functionalities as privileged structural elements in biologically active compounds and exploitation of their synthetic chemistry

SRSS Kotti et al.

CHEMICAL BIOLOGY & DRUG DESIGN (2006)

添加到收藏夹

Review Chemistry, Multidisciplinary

α,β-Diamino acids:: Biological significance and synthetic approaches

A Viso et al.

CHEMICAL REVIEWS (2005)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantio- and diastereoselective catalytic Mannich-type reaction of a glycine Schiff base using a chiral two-center phase-transfer catalyst

A Okada et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2005)

添加到收藏夹

Article Chemistry, Organic

Synthesis of a novel C2-symmetric thiourea and its application in the Pd-catalyzed cross-coupling reactions with arenediazonium salts under aerobic conditions

MJ Dai et al.

ORGANIC LETTERS (2004)

添加到收藏夹

Article Chemistry, Organic

Catalytic asymmetric synthesis of a nitrogen analogue of dialkyl tartrate by direct Mannich reaction under phase-transfer conditions

T Ooi et al.

ORGANIC LETTERS (2004)

添加到收藏夹

Article Chemistry, Organic

Catalytic asymmetric Mannich reactions of glycine derivatives with imines.: A new approach to optically active α,β-diamino acid derivatives

L Bernardi et al.

JOURNAL OF ORGANIC CHEMISTRY (2003)

添加到收藏夹

© Peeref 2019-2024. All rights reserved.