Photoactive Ni-Complexes in Metallaphotoredox Catalysis: A Successful Match in C –C Cross-Coupling Reactions
Conclusion [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text (Source: Synthesis)
Source: Synthesis - April 8, 2024 Category: Chemistry Authors: Dang, Luzhen Zhu, Chuan Feng, Chao Tags: short review Source Type: research
Iodosulfonylation of [1.1.1]Propellane
Synthesis DOI: 10.1055/a-2290-6540 An efficient disubstituted functionalization of [1.1.1]propellane has been developed. The protocol utilizes sulfonyl hydrazides and N-iodosuccinimide, enabling the introduction of iodine and sulfonyl groups into bicyclo[1.1.1]pentane (BCP) in moderate to excellent yields. It has the advantages of simple operation, mild conditions, and broad substrate scope. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text (Source: Synthesis)
Source: Synthesis - April 8, 2024 Category: Chemistry Authors: Chen, Mengke Ling, Min Huang, Zhiwei Cheng, Dongping Li, Jing-Hua Tags: paper Source Type: research
Diastereoselective Synthesis of NH-Unprotected Spiropyrrolidines via the Huisgen Reaction of Acenaphthoquinone-Derived Azomethine Ylides with β-Nitrostyrenes
Synthesis DOI: 10.1055/s-0042-1751581 4′-Nitro-2H-spiro[acenaphthylene-1,2′-pyrrolidine]-2-one derivatives are prepared via [3+2] cycloaddition reactions of azomethine ylides, generated in situ from acenaphthoquinone and primary amines, with β-nitrostyrenes in the presence of (
i
Pr)2NEt in methanol. Evidence for the structures of the products was obtained from single-crystal X-ray analysis. The important feature of this diastereoselective synthesis of NH-unprotected spiropyrrolidines is the formation of four contiguous stereogenic centers, one of which is quaternary, with high selectivity. [...] Georg Th...
Source: Synthesis - April 4, 2024 Category: Chemistry Authors: Yavari, Issa Ghafouri, Kiyana Tags: paper Source Type: research
Asymmetric Hydrogenative Coupling of Indoles with Unsaturated Ketones Enabled by Copper/Ruthenium Relay Catalysis
Synthesis DOI: 10.1055/a-2295-5417 A relay catalytic system is developed for the asymmetric hydrogenative coupling of indoles with α,β-unsaturated ketones, affording enantioenriched chiral γ-indole alcohols with broad substrate scope and excellent enantioselectivities (32 examples, up to >99% ee). Mechanistic studies suggest that the relay catalytic system consists of copper-catalyzed alkylation and ruthenium-catalyzed asymmetric hydrogenation. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text (Source: Synthesis)
Source: Synthesis - April 3, 2024 Category: Chemistry Authors: Zhang, Jian Guo, Chen Tang, Weijun Xue, Dong Sun, Huaming Xiao, Jianliang Wang, Chao Tags: paper Source Type: research
Synthesis of Heteroaromatic-Fused Cyclic β-Amino Acids by Rhodium-Catalyzed Electrophilic Amination
Synthesis DOI: 10.1055/a-2282-7450 A series of cyclic β-amino acids fused with heteroaromatic moieties was prepared by Rh-catalyzed electrophilic amination. The transformation involves a rhodium alkyl nitrene generated from substituted isoxazolidin-5-ones upon the N–O bond cleavage. These products contain an underexplored class of cyclic structures that may have specific applications in various chemistry disciplines. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text (Source: Synthesis)
Source: Synthesis - April 3, 2024 Category: Chemistry Authors: Manoharan, Ramasamy Asada, Yasuko Noda, Hidetoshi Shibasaki, Masakatsu Tags: paper Source Type: research
A Photochemical Strategy for the Synthesis of Caprolactams via Dearomative Ring Expansion of Nitroarenes
Synthesis DOI: 10.1055/a-2288-6944 This paper outlines a novel strategy for the preparation of seven-membered-ring lactams from simple nitroarenes. The approach is based on a photochemical dearomative ring expansion starting with the conversion of the nitro group into a singlet nitrene. This process is mediated by blue light, occurs at room temperature and overall enables the insertion of the nitro N-atom into the benzenoid framework. This step transforms the aromatic starting material into a seven-membered ring azepine that, following hydrogenation and hydrolysis, is converted into the desired caprolactams in just three s...
Source: Synthesis - April 2, 2024 Category: Chemistry Authors: S ánchez-Bento, Raquel Bui, Linda Duong, Vincent K. Ruffoni, Alessandro Leonori, Daniele Tags: paper Source Type: research
N-Triflyl Phosphoric Triamide (N-TPT) as an Efficient Activator for ‘On-Water’ Accelerated Aquacatalytic Polar Substrate Allylation
We report herein the triple hydrogen-bonding donor activator N-triflyl phosphoric triamide (
N-TPT) for the synergistic Brønsted acid aquacatalysis of multicomponent allylation ‘on-water’. The reaction demonstrated remarkable efficiency in converting polar diol substrate, such as 1,3-dihydroxyacetone, into α-tertiary amine derivative incorporating homoallylic amine functionalities using bulk water as the reaction medium. The single crystal X-ray structure and control experiments highlighted the crucial role of multiple hydrogen bonds in enabling this aqueous reaction. [...] Georg Thieme Verlag KG RüdigerstraÃ...
Source: Synthesis - April 2, 2024 Category: Chemistry Authors: Kim, Hyun Jin Shin, Myoung Hyeon Kim, Woo Hee Park, Jin Hyun Lee, Gang Min Bae, Han Yong Tags: paper Source Type: research
Synthesis of N-Trifluoromethyl Thiocarbamates and Ureas from 3-Aminopyridine-Derived Carbamates
Synthesis DOI: 10.1055/a-2290-6614 The synthesis of N-trifluoromethyl thiocarbamates and ureas from 3-pyridyl isothiocyanates via the nucleophilic substitution reaction of perfluorophenyl pyridin-3-yl(trifluoromethyl)carbamate is described. Recently, Schoenebeck’s group reported a straightforward method to access N-trifluoromethyl analogues of amides and related carbonyl compounds. However, N-trifluoromethyl thiocarbamates and ureas derived from pyridine-containing amines remain a synthetic challenge. In this paper, the strategy relies on the operationally simple preparation of perfluorophenyl pyridin-3-yl(trifluoromethy...
Source: Synthesis - April 2, 2024 Category: Chemistry Authors: He, Xingjin Deng, Linbei You, Ying Lai, Yongxing Liu, Jianbo Tags: paper Source Type: research
Photoredox-Catalyzed Oxidative C –H Alkylation of Glycine Derivatives with 4-Alkyl-1,4-dihydropyridines
Synthesis DOI: 10.1055/a-2284-9845 Oxidative α-C(sp3)–H alkylation of N-arylated glycine derivatives with 4-alkyldihydropyridine derivatives (alkyl-DHPs) as versatile alkyl radical precursors has been developed. Utilizing visible-light-driven photoredox catalysis and ammonium persulfate as an oxidizing agent, this methodology facilitates the site-selective alkylation of glycine derivatives, enabling the site-selective alkylation of peptides. The reaction exhibits broad substrate scope, including various alkyl radicals and acid-labile functional groups. This approach expands the synthetic toolbox in peptide chemistry, of...
Source: Synthesis - April 2, 2024 Category: Chemistry Authors: Babu, Madala Hari Jang, Eunbin Jang, Hyesu Kim, Sang Kyum Sim, Jaehoon Tags: paper Source Type: research
Base-Mediated Synthesis of 2-Bromobenzoheterocycles
Synthesis DOI: 10.1055/s-0042-1751577 A base-mediated cyclization to synthesize 2-bromobenzoheterocycles is reported. This transformation was demonstrated with 16 examples to access a broad range of brominated benzoheterocycles. Mechanistic studies support the reaction proceeds through a bromoalkyne, and revealed an exchangeable proton at C3 of the indole products. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text (Source: Synthesis)
Source: Synthesis - April 2, 2024 Category: Chemistry Authors: Arora, Ramon Li, Shangyu Stommer, Maik Mirabi, Bijan Lautens, Mark Tags: paper Source Type: research
Synthesis and Biological Activity of Penaresidins A and B, Penazetidine A, and Related Analogues
Synthesis DOI: 10.1055/s-0043-1763676 Since the first reports of their isolation, penaresidins A and B together with penazetidine A and related analogues have attracted interest from the synthetic community for their unique structural features, specifically the highly functionalized azetidine core. This review provides a comprehensive overview of the biological activity of the penaresidins, penazetidine, and their analogues together with reported synthetic strategies developed since their isolation.1 Introduction2 Biological Activity of Penaresidin A, Penaresidin B, and Penazetidine A and Related Analogues3 Retrosynthet...
Source: Synthesis - March 28, 2024 Category: Chemistry Authors: Burns, Sean M. McClure, Timothy J. Parikh, Seren G. Schindler, Corinna S. Tags: review Source Type: research
Linked PDF of Table of Contents
Synthesis 2024; 56: V- DOI: 10.1055/s-0040-1720111 Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents (Source: Synthesis)
Source: Synthesis - March 26, 2024 Category: Chemistry Tags: table of contents Source Type: research
Lanthanoids in Hydroarylaminations: Yb(III)- and Tb(III)-Catalyzed Addition of Arylamines to Activated Olefins
Synthesis DOI: 10.1055/a-2282-7702 Michael-type hydroaminations of acrylonitrile, phenyl vinyl sulfone, and dimethyl maleate were realized using arylamines catalyzed independently by Yb(OTf)3 and Tb(OTf)3 to give the desired β-aminonitriles, β-amino sulfones, and dimethyl aspartates, respectively, in moderate to excellent yields. The reactions were carried out in toluene for Yb(OTf)3 and in t-BuOMe for Tb(OTf)3, all reactions were performed at 100 °C. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text (Source: Synthesis)
Source: Synthesis - March 25, 2024 Category: Chemistry Authors: Rajesh, Rajagopal Sandhya, Olencheri Karimpanakkal Narayanan, Sunilkumar Puthenpurackal Kunjanpillai, Rajesh Tags: paper Source Type: research
One-Pot N- α-C(sp3)–H Bond Functionalisation Cascade for the Synthesis of Polysubstituted Imidazoles
Synthesis DOI: 10.1055/s-0043-1763690 A one-pot eco-friendly oxidative N-α-C(sp3)–H bond functionalisation of arylmethylamines for the synthesis of tetrasubstituted imidazoles is demonstrated. The substrate scope of these amines has been well-explored with different substrates, such as 1,2-diketones, an α-hydroxy ketone and phenylacetophenone. In the presence of FeCl3 catalyst and green oxidant O2, the easily accessible substrates afforded tetrasubstituted imidazoles in up to 94% yield. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstra...
Source: Synthesis - March 25, 2024 Category: Chemistry Authors: Kadu, Vikas D. Sankala, Naga Chandradudu Hublikar, Mahesh G. Bansode, Shahaji I. Bhosale, Raghunath B. Tags: paper Source Type: research
Use of Aliphatic Carboxylic Acid Derivatives for NHC/Photoredox-Catalyzed meta-Selective Acylation of Electron-Rich Arenes
We describe the use of acyl imidazoles derived from aliphatic carboxylic acids for the N-heterocyclic carbene/organic photoredox co-catalyzed meta-selective functionalization of electron-rich arenes. Compared to our previous work, a change of the wavelength of the applied LED light from 440 nm to 390 nm promotes this reaction efficiently. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text (Source: Synthesis)
Source: Synthesis - March 25, 2024 Category: Chemistry Authors: Goto, Yamato Murakami, Sho Sumida, Yuto Ohmiya, Hirohisa Tags: paper Source Type: research
