Browse
Submit Data
Databases
API
Help

Dataset Information

29 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

DABO Boronates: Stable Heterocyclic Boronic Acid Complexes for Use in Suzuki-Miyaura Cross-Coupling Reactions.

ABSTRACT: Diethanolamine complexed heterocyclic boronic acids (DABO boronates) are air-stable reagents that can be used directly in Suzuki-Miyaura reactions in the presence of water or a protic co-solvent. Interestingly, heterocyclic DABO boronates can be stored for extended periods of time at room temperature with no noticeable degradation, unlike their boronic acid counterparts. Heterocyclic DABO boronates constitute an operationally simple and efficient alternative to other boronic acid derivatives as coupling partners in palladium catalyzed cross-coupling reactions under standard Suzuki-Miyaura conditions.

SUBMITTER: Reilly MK

PROVIDER: S-EPMC3870905 | biostudies-literature | 2011 Oct

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

DABO Boronates: Stable Heterocyclic Boronic Acid Complexes for Use in Suzuki-Miyaura Cross-Coupling Reactions.

Reilly Maureen K MK Rychnovsky Scott D SD

Synlett : accounts and rapid communications in synthetic organic chemistry 20111001 16

Diethanolamine complexed heterocyclic boronic acids (DABO boronates) are air-stable reagents that can be used directly in Suzuki-Miyaura reactions in the presence of water or a protic co-solvent. Interestingly, heterocyclic DABO boronates can be stored for extended periods of time at room temperature with no noticeable degradation, unlike their boronic acid counterparts. Heterocyclic DABO boronates constitute an operationally simple and efficient alternative to other boronic acid derivatives as ...[more]

PMID: 24371372

Similar Datasets

N-Heterocyclic Carbene Ligand-Controlled Chemodivergent Suzuki-Miyaura Cross Coupling.

Project description:Two N-heterocyclic carbene ligands provide orthogonal chemoselectivity during the Pd-catalyzed Suzuki-Miyaura (SM) cross-coupling of chloroaryl triflates. The use of SIPr [SIPr = 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene] leads to selective cross-coupling at chloride, while the use of SIMes [SIMes = 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene] provides selective coupling at triflate. With most chloroaryl triflates and arylboronic acids, ligand-controlled selectivity is high (?10:1). The scope of this methodology is significantly more general than previously reported methods for selective SM coupling of chloroaryl triflates using phosphine ligands. Density functional theory studies suggest that palladium's ligation state during oxidative addition is different with SIMes compared to SIPr.

| S-EPMC6754280 | biostudies-literature

Anhydrous, Homogeneous, Suzuki-Miyaura Cross-Coupling of Boronic Esters using Potassium Trimethylsilanolate.

Project description: Not available

| S-EPMC7808858 | biostudies-literature

Potassium Trimethylsilanolate Enables Rapid, Homogeneous Suzuki-Miyaura Cross-Coupling of Boronic Esters.

Project description:Herein, a mild and operationally simple method for the Suzuki-Miyaura cross-coupling of boronic esters is described. Central to this advance is the use of the organic-soluble base, potassium trimethylsilanolate, which allows for a homogeneous, anhydrous cross-coupling. The coupling proceeds at a rapid rate, often furnishing products in quantitative yield in less than 5 min. By applying this method, a >10-fold decrease in reaction time was observed for three published reactions which required >48 h to reach satisfactory conversion.

| S-EPMC7880502 | biostudies-literature

Suzuki-Miyaura cross-coupling of 3-pyridyl triflates with 1-alkenyl-2-pinacol boronates.

Project description:Palladium-catalyzed Suzuki-type couplings of 3-pyridyl triflates with alkenyl pinacol boronates proceed in good to excellent yield. Optimized conditions use Pd(PPh(3))(4) (10 mol %) as catalyst with K(3)PO(4) (3 equiv) as base in dioxane.

| S-EPMC3080250 | biostudies-literature

Suzuki-Miyaura cross-coupling reactions of benzyl halides with potassium aryltrifluoroborates.

Project description:[reaction: see text] The palladium-catalyzed cross-coupling of potassium aryltrifluoroborates with benzylic halides occurs in good yield with high functional group tolerance. The increased stability of potassium aryltrifluoroborates compared to other boron coupling partners makes this an effective route to functionalized methylene-linked biaryl systems.

| S-EPMC2515367 | biostudies-other

Synthesis, characterization and evaluation of bulky bis(pyrazolyl)palladium complexes in Suzuki-Miyaura cross-coupling reactions.

Project description:Pyrazole-containing compounds have been used in recent times as ligands to stabilize metal complexes used as pre-catalysts in cross-coupling reactions. With various substituents at various positions in the pyrazole ring, the overall electrophilic and steric properties of the metal complexes can be fine-tuned. Herein, we report the synthesis of bulky pyrazole-based ligands by condensation of methyl 4-(bromomethyl)benzoate or benzyl bromide with various substituted pyrazole compounds. These ligands were utilised in the synthesis of bis(pyrazolyl)palladium(ii) complexes. The complexes' catalytic activity in Suzuki-Miyaura cross-coupling reactions was evaluated. Phenyl bearing pre-catalyst 7, at a catalyst loading of 0.33 mol%, successfully converted 98% of bromobenzene and phenylboronic acid to biphenyl in 4 h at 140 °C, while the tertiary butyl bearing pre-catalyst 8 converted up to 81% of the same substrates to biphenyl. An increase in conversion was seen for all pre-catalysts when an electron-withdrawing substituent was present on the aryl halide substrate, and the opposite was observed when the electron-withdrawing group was present on the phenyl boronic acid.

| S-EPMC9079791 | biostudies-literature

Suzuki-Miyaura reactions catalyzed by C₂-symmetric Pd-multi-dentate N-heterocyclic carbene complexes.

Project description:Suzuki-Miyaura coupling reactions are promoted by Pd complexes ligated with C₂-symmetric multi-dentate N-heterocyclic carbenes derived in situ from Pd(OAc)₂ and imidazolium salts. Good to excellent yields were obtained for aryl bromides as substrates. Turnover numbers of up to 10⁵ could be achieved with 5 × 10⁻⁴ mol% of Pd(OAc)₂/1 × 10⁻³ mol% NHC precatalyst in 24 h.

| S-EPMC6268461 | biostudies-literature

Suzuki-Miyaura cross-coupling reactions of primary alkyltrifluoroborates with aryl chlorides.

Project description:Parallel microscale experimentation was used to develop general conditions for the Suzuki-Miyaura cross-coupling of diversely functionalized primary alkyltrifluoroborates with a variety of aryl chlorides. These conditions were found to be amenable to coupling with aryl bromides, iodides, and triflates as well. The conditions that were previously identified through similar techniques to promote the cross-coupling of secondary alkyltrifluoroborates with aryl chlorides were not optimal for the primary alkyltrifluoroborates, thus demonstrating the value of parallel experimentation to develop novel, substrate specific results.

| S-EPMC2696385 | biostudies-literature

Scope of the Suzuki-Miyaura cross-coupling reactions of potassium heteroaryltrifluoroborates.

Project description:A wide variety of bench-stable potassium heteroaryltrifluoroborates were prepared, and general reaction conditions were developed for their cross-coupling to aryl and heteroaryl halides. The cross-coupled products were obtained in good to excellent yields. This method represents an efficient and facile installation of heterocyclic building blocks onto preexisting organic substructures.

| S-EPMC2664078 | biostudies-literature

Water-soluble SNS cationic palladium(II) complexes and their Suzuki-Miyaura cross-coupling reactions in aqueous medium.

Project description:Unlike their SCS analogues, SNS pincer complexes are poorly studied for their use in coupling reactions. Accordingly, a series of water soluble cationic Pd(II) SNS pincer complexes have been successfully synthesised and investigated in detail for their catalytic activity in Suzuki-Miyaura coupling reactions. By using only 0.5 mol % loading of the complexes, the coupling of inactivated aryl bromides and activated aryl chlorides with various boronic acids in water was achieved in excellent yields and the catalysts were found to be reusable for three cycles without a significant loss of activity. The investigation of the mechanism of the reaction revealed that a Pd(II) to Pd(IV) route is the more likely pathway which was further supported by computational studies.

| S-EPMC6071702 | 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