Browse
Submit Data
Databases
API
Help

Dataset Information

28 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Nickel-Catalyzed Conversion of Enol Triflates into Alkenyl Halides.

ABSTRACT: A Ni-catalyzed halogenation of enol triflates was developed and it enables the synthesis of a broad range of alkenyl iodides, bromides, and chlorides under mild reaction conditions. The reaction utilizes inexpensive, bench-stable Ni(OAc)2 ?4?H2 O as a precatalyst and proceeds at room temperature in the presence of sub-stoichiometric Zn and either 1,5-cyclooctadiene or 4-(N,N-dimethylamino)pyridine.

SUBMITTER: Hofstra JL

PROVIDER: S-EPMC7179072 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Nickel-Catalyzed Conversion of Enol Triflates into Alkenyl Halides.

Hofstra Julie L JL Poremba Kelsey E KE Shimozono Alex M AM Reisman Sarah E SE

Angewandte Chemie (International ed. in English) 20190919 42

A Ni-catalyzed halogenation of enol triflates was developed and it enables the synthesis of a broad range of alkenyl iodides, bromides, and chlorides under mild reaction conditions. The reaction utilizes inexpensive, bench-stable Ni(OAc)<sub>2</sub> ⋅4 H<sub>2</sub> O as a precatalyst and proceeds at room temperature in the presence of sub-stoichiometric Zn and either 1,5-cyclooctadiene or 4-(N,N-dimethylamino)pyridine. ...[more]

PMID: 31410936

Similar Datasets

Nickel-catalyzed Kumada cross-coupling reactions of tertiary alkylmagnesium halides and aryl bromides/triflates.

Project description:We report a Ni-catalyzed process for the cross-coupling of tertiary alkyl nucleophiles and aryl bromides. This process is extremely general for a wide range of electrophiles and generally occurs with a ratio of retention to isomerization >30:1. The same procedure also accommodates the use of aryl triflates, vinyl chlorides, and vinyl bromides as the electrophilic component.

| S-EPMC8036247 | biostudies-literature

Enantioselective Electroreductive Coupling of Alkenyl and Benzyl Halides via Nickel Catalysis.

Project description:An electrochemically-driven enantioselective nickel-catalyzed reductive cross-coupling of alkenyl bromides and benzyl chlorides is reported. The reaction forms products bearing allylic stereogenic centers with good enantioselectivity under mild conditions in an undivided cell. Electrochemical activation and turnover of the catalyst mitigate issues posed by metal powder reductants. This report demonstrates that enantioselective Ni-catalyzed cross-electrophile couplings can be driven electrochemically.

| S-EPMC7190267 | biostudies-literature

Nickel-catalyzed coupling of alkenes, aldehydes, and silyl triflates.

Project description:A full account of two recently developed nickel-catalyzed coupling reactions of alkenes, aldehydes, and silyl triflates is presented. These reactions provide either allylic alcohol or homoallylic alcohol derivatives selectively, depending on the ligand employed. These processes are believed to be mechanistically distinct from Lewis acid-catalyzed carbonyl-ene reactions, and several lines of evidence supporting this hypothesis are discussed.

| S-EPMC3148200 | biostudies-literature

Palladium-catalyzed regiocontrolled alpha-arylation of trimethylsilyl enol ethers with aryl halides.

Project description:Inter- and intramolecular arylations of trimethylsilyl enol ethers with aryl halides are accomplished regiospecifically in the presence of a palladium catalyst and tributyltin fluoride in refluxing benzene or toluene. The optimal catalyst system called for the use of Pd2(dba)3 and tri-tert-butylphosphine in ca. 1:2 ratio. Aryl iodides, bromides, and chlorides are all effective arylation partners in this reaction. [reaction: see text]

| S-EPMC2518395 | biostudies-literature

Directed nickel-catalyzed 1,2-dialkylation of alkenyl carbonyl compounds.

Project description:A nickel-catalyzed conjunctive cross-coupling of non-conjugated alkenes, alkyl halides, and alkylzinc reagents is reported. Regioselectivity is controlled by chelation of a removable bidentate 8-aminoquinoline directing group. Under optimized conditions, a wide range of 1,2-dialkylated products can be accessed in moderate to excellent yields. To the best of our knowledge, this report represents the first example of three-component 1,2-dialkylation of non-conjugated alkenes to introduce differentiated alkyl fragments.

| S-EPMC6001383 | biostudies-literature

Directed, nickel-catalyzed 1,2-alkylsulfenylation of alkenyl carbonyl compounds.

Project description:We report a regioselective, nickel-catalyzed syn-1,2-carbosulfenylation of non-conjugated alkenyl carbonyl compounds with alkyl/arylzinc nucleophiles and tailored N-S electrophiles. This method allows the simultaneous installation of a variety of C(sp3) and S(Ar) (or Se(Ar)) groups onto unactivated alkenes, which complements previously developed 1,2-carbosulfenylation methodology in which only C(sp2) nucleophiles are compatible. A bidentate directing auxiliary controls regioselectivity, promotes high syn-stereoselectivity with a variety of E- and Z-internal alkenes, and enables the use of an array of electrophilic sulfenyl (and seleno) electrophiles. Among compatible electrophiles, those with N-alkyl-benzamide leaving groups were found to be especially effective, as determined through comprehensive structure-reactivity mapping.

| S-EPMC9172569 | biostudies-literature

Zinc(II) catalyzed conversion of alkynes to vinyl triflates in the presence of silyl triflates.

Project description:The conversion of alkynes to their corresponding vinyl triflates in the presence of stoichiometric TMS-triflate was greatly facilitated by the triflate salt of several transition metal catalysts most especially Zn(OTf)2. Products are formed in high regioselectivity under mild conditions. Internal alkynes bearing an aryl substituent afford vinyl triflates with a modest preference for the Z-isomer especially with larger substituents. A mechanism is put forward to explain the unique role of silicon in this system.

| S-EPMC4136703 | biostudies-literature

Mild palladium-catalyzed cyanation of (hetero)aryl halides and triflates in aqueous media.

Project description:A mild, efficient, and low-temperature palladium-catalyzed cyanation of (hetero)aryl halides and triflates is reported. Previous palladium-catalyzed cyanations of (hetero)aryl halides have required higher temperatures to achieve good catalytic activity. This current reaction allows the cyanation of a general scope of (hetero)aryl halides and triflates at 2-5 mol % catalyst loadings with temperatures ranging from rt to 40 °C. This mild method was applied to the synthesis of lersivirine, a reverse transcriptase inhibitor.

| S-EPMC4301087 | biostudies-literature

Stereoretentive Pd-catalyzed Kumada-Corriu couplings of alkenyl halides at room temperature.

Project description:Stereoselective palladium-catalyzed Kumada-Corriu reactions of functionalized alkenyl halides and a variety of Grignard reagents, including those bearing ?-hydrogen atoms and sensitive functional groups, can be carried out at room temperature using a new combination of reagents.

| S-EPMC4136712 | biostudies-literature

Pd-catalyzed conversion of aryl chlorides, triflates, and nonaflates to nitroaromatics.

Project description:An efficient Pd catalyst for the transformation of aryl chlorides, triflates, and nonaflates to nitroaromatics has been developed. This reaction proceeds under weakly basic conditions and displays a broad scope and excellent functional group compatibility. Moreover, this method allows for the synthesis of aromatic nitro compounds that cannot be accessed efficiently via other nitration protocols. Mechanistic insight into the transmetalation step of the catalytic process is also reported.

| S-EPMC2773681 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data