Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Palladium-Catalyzed C2-Selective Oxidative Olefination of Benzo[b]thiophene 1,1-Dioxides with Styrenes and Acrylates.

ABSTRACT: Here, we disclose a novel Pd(II)-catalyzed oxidative Heck reaction of benzo[b]thiophene 1,1-dioxides with styrenes and acrylates. This transformation features broad functional group tolerance and high C2 selectivity. Furthermore, the photoluminescence properties of C-2 alkenylated products have been characterized, which illustrates the potential usefulness of our protocol in constructing π-conjugated fluorescent molecules.

SUBMITTER: Yang B

PROVIDER: S-EPMC10034782 | biostudies-literature | 2023 Mar

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Palladium-Catalyzed C2-Selective Oxidative Olefination of Benzo[b]thiophene 1,1-Dioxides with Styrenes and Acrylates.

Yang Bingbin B Lu Yaoyao Y Duan Luqiong L Ma Xiaoyu X Xia Yaolin Y Huang Xiaolei X

ACS omega 20230310 11

Here, we disclose a novel Pd(II)-catalyzed oxidative Heck reaction of benzo[b]thiophene 1,1-dioxides with styrenes and acrylates. This transformation features broad functional group tolerance and high C2 selectivity. Furthermore, the photoluminescence properties of C-2 alkenylated products have been characterized, which illustrates the potential usefulness of our protocol in constructing π-conjugated fluorescent molecules. ...[more]

PMID: 36969423

Similar Datasets

Palladium-Catalyzed C2-Selective Direct Arylation of Benzo[b]thiophene 1,1-Dioxides with Arylboronic Acids

Project description: Not available

| S-EPMC10785645 | biostudies-literature

Efficient synthesis of chiral 2,3-dihydro-benzo[b]thiophene 1,1-dioxides via Rh-catalyzed hydrogenation.

Project description:Rh-catalyzed asymmetric hydrogenation of prochiral substituted benzo[b]thiophene 1,1-dioxides was successfully developed, affording various chiral 2,3-dihydrobenzo[b]thiophene 1,1-dioxides with high yields and excellent enantioselectivities (up to 99% yield and >99% ee). In particular, for challenging substrates, such as aryl substituted substrates with sterically hindered groups and alkyl substituted substrates, the reaction proceeded smoothly in our catalytic system with excellent results. The gram-scale asymmetric hydrogenation proceeded well with 99% yield and 99% ee in the presence of 0.02 mol% (S/C = 5000) catalyst loading. The possible hydrogen-bonding interaction between the substrate and the ligand may play an important role in achieving high reactivity and excellent enantioselectivity.

| S-EPMC6385876 | biostudies-literature

Synthesis and anti-tubercular activity of 3-substituted benzo[b]thiophene-1,1-dioxides.

Project description:We demonstrated that the 3-substituted benzothiophene-1,1-dioxide class of compounds are effective inhibitors of Mycobacterium tuberculosis growth under aerobic conditions. We examined substitution at the C-3 position of the benzothiophene-1,1-dioxide series systematically to delineate structure-activity relationships influencing potency and cytotoxicity. Compounds were tested for inhibitory activity against virulent M. tuberculosis and eukaryotic cells. The tetrazole substituent was most potent, with a minimum inhibitory concentration (MIC) of 2.6 µM. However, cytotoxicity was noted with even more potency (Vero cell TC50 = 0.1 µM). Oxadiazoles had good anti-tubercular activity (MICs of 3-8 µM), but imidazoles, thiadiazoles and thiazoles had little activity. Cytotoxicity did not track with anti-tubercular activity, suggesting different targets or mode of action between bacterial and eukaryotic cells. However, we were unable to derive analogs without cytotoxicity; all compounds synthesized were cytotoxic (TC50 of 0.1-5 µM). We conclude that cytotoxicity is a liability in this series precluding it from further development. However, the series has potent anti-tubercular activity and future efforts towards identifying the mode of action could result in the identification of novel drug targets.

| S-EPMC4193402 | biostudies-literature

Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation of Thietane 1,1-Dioxides.

Project description:A palladium-catalyzed decarboxylative asymmetric allylic alkylation of thietane 1,1-dioxides via linear enolate intermediates from racemic starting materials has been developed. This process installs an α-sulfonyl tetrasubstituted stereogenic center with high enantioselectivity. The potential to transform the alkylated products to novel types of enantioenriched spirocycles for medicinal chemistry applications has also been demonstrated.

| S-EPMC8762707 | biostudies-literature

Electrochemically-promoted synthesis of benzo[b]thiophene-1,1-dioxides via strained quaternary spirocyclization.

Project description:We report an approach for the synthesis of benzothiophene motifs under electrochemical conditions by the reaction of sulfonhydrazides with internal alkynes. Upon the formation of a quaternary spirocyclization intermediate by the selective ipso-addition instead of an ortho-attack, the S-migration process was rationalized to lead to the products. Computational studies revealed the selectivity and the compatibility of drug molecules showcased the potential application of the protocols.

| S-EPMC9431990 | biostudies-literature

Diverse methyl sulfone-containing benzo[b]thiophene library via iodocyclization and palladium-catalyzed coupling.

Project description:Parallel solution-phase methods for the synthesis of a 72-membered benzo[b]thiophene library are reported. Medicinally interesting, drug-like, methyl sulfone-substituted benzo[b]thiophenes have been prepared by the palladium-catalyzed substitution of 3-iodobenzo[b]thiophenes by Suzuki-Miyaura, Sonogashira, Heck, carboalkoxylation, and aminocarbonylation chemistry. The key intermediates for library generation, methyl sulfone-containing 3-iodobenzo[b]thiophenes, are readily prepared by iodocyclization and oxidation methodologies from readily available alkynes.

| S-EPMC2834800 | biostudies-literature

Asymmetric palladium-catalyzed directed intermolecular fluoroarylation of styrenes.

Project description:A mild catalytic asymmetric direct fluoro-arylation of styrenes has been developed. The palladium-catalyzed three-component coupling of Selectfluor, a styrene and a boronic acid, provides chiral monofluorinated compounds in good yield and in high enantiomeric excess. A mechanism proceeding through a Pd(IV)-fluoride intermediate is proposed for the transformation and synthesis of an sp(3) C-F bond.

| S-EPMC3971964 | biostudies-literature

Palladium-catalyzed difluoroalkylative carbonylation of styrenes toward difluoropentanedioates.

Project description:The introduction of fluorine atoms into organic molecules is an attractive but challenging topic. In this work, an interesting palladium-catalyzed difluoroalkylative carbonylation of aryl olefins has been developed. A wide range of aryl olefins were transformed into the corresponding difluoropentanedioate compounds with good functional-group tolerance and excellent regioselectivity. Inexpensive ethyl bromodifluoroacetate acts both as a difluoroalkyl precursor and a nucleophile here. Additionally, a scale-up reaction was also performed successfully, and further transformations of the obtained product were shown as well.

| S-EPMC9384137 | biostudies-literature

Asymmetric palladium-catalyzed hydroarylation of styrenes and dienes.

Project description:Alkenes are desirable and highly versatile starting materials for organic transformations, and well-known substrates for palladium catalysis. Typically, these reactions result in the formation of a new alkene product via β-hydride elimination. In contrast to this scenario, our laboratory has been involved in the development of alkene hydro- and difunctionalization reactions, where β-hydride elimination can be controlled. We report herein the development of an asymmetric palladium-catalyzed hydroarylation, which yields diarylmethine products in up to 75% ee. Interestingly, a linear free energy relationship is observed between the steric bulk of the ligand within a certain range and the enantiomeric excess of the reaction.

| S-EPMC3129978 | biostudies-literature

Palladium-catalyzed 1,1-difunctionalization of ethylene.

Project description:The 1,1-difunctionalization of ethylene, with aryl/vinyl/heteroaryl transmetalating agents and vinyl electrophiles, is reported. The reaction is high-yielding under a low pressure of ethylene, and regioselectivity is generally high for the 1,1-disubstituted product. The process is highlighted by the use of heteroaromatic cross-coupling reagents, which have not been competent reaction partners in previously reported efforts.

| S-EPMC3459322 | biostudies-literature