Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

3-Boryl-2,1-borazaronaphthalene: Umpolung Reagents for Diversifying Naphthalene Isosteres.

ABSTRACT: A Pd-catalyzed Miyaura borylation of 3-bromo-2,1-borazaronaphthalenes is reported. This method allows the formation of umpolung reagents for subsequent Pd-mediated cross-coupling. Coupling of this nucleophilic partner with a variety of commercially available aryl- and heteroaryl halides allows facile and rapid diversification of these cores.

SUBMITTER: Compton JS

PROVIDER: S-EPMC6097885 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

3-Boryl-2,1-borazaronaphthalene: Umpolung Reagents for Diversifying Naphthalene Isosteres.

Compton Jordan S JS Saeednia Borna B Kelly Christopher B CB Molander Gary A GA

The Journal of organic chemistry 20180710 16

A Pd-catalyzed Miyaura borylation of 3-bromo-2,1-borazaronaphthalenes is reported. This method allows the formation of umpolung reagents for subsequent Pd-mediated cross-coupling. Coupling of this nucleophilic partner with a variety of commercially available aryl- and heteroaryl halides allows facile and rapid diversification of these cores. ...[more]

PMID: 29989812

Similar Datasets

Simple access to elusive α-boryl carbanions and their alkylation: an umpolung construction for organic synthesis.

Project description:The reaction of 1,1-bis(pinacolboronate) esters with alkyl halides can be effected by metal alkoxides and provides a strategy for the construction of organoboronate compounds. The reaction is found to occur by alkoxide-induced deborylation and generation of a boron-stabilized carbanion.

| S-EPMC4353009 | biostudies-literature

3,3'-{1,1'-Methyl-enebis[naphthalene-2,1-diylbis(oxymethyl-ene)]}dibenzonitrile.

Project description:The title compound, C(37)H(26)N(2)O(2), was synthesized from 1,1'-methyl-enedinaphthalen-2-ol and 3-(bromo-methyl)-benzo-nitrile. The two naphthyl systems are almost perpendicular to each other [dihedral angle 83.3?(9)°] and the two cyano-benz-yloxy rings approximately parallel to each other [dihedral angle 15.5?(2)°].

| S-EPMC2961493 | biostudies-literature

Di-tert-Butyl 2,2'-[2,2'-methyl-enebis(naphthalene-2,1-diyldi-oxy)]diacetate.

Project description:In the title compound, C(33)H(36)O(6), two naphthalene ring systems are connected through a methyl-ene linkage [C-C-C = 114.9 (2)°]; the ring systems are aligned at an angle of 76.5 (1)°. Of the two -O-CH(2)-C(=O)-C(CH(3))(3) substituents, one adopts an extended conformation whereas the other is U-shaped. In the crystal, mol-ecules are linked via weak C-H⋯O hydrogen bonding, forming supra-molecular chains running along the c axis.

| S-EPMC3051626 | biostudies-literature

Boryl (Hetero)aryne Precursors as Versatile Arylation Reagents: Synthesis through C-H Activation and Orthogonal Reactivity.

Project description:(Pinacolato)boryl ortho-silyl(hetero)aryl triflates are presented as a new class of building blocks for arylation. They demonstrate unique versatility by delivering boronate or (hetero)aryne reactivity chemoselectively in a broad range of transformations. This approach enables the unprecedented postfunctionalization of fluoride-activated (hetero)aryne precursors, for example, as substrates in transition-metal catalysis, and offers valuable new possibilities for aryl boronate postfunctionalization without the use of specialized protecting groups.

| S-EPMC4600243 | biostudies-literature

4,4'-{[1,1'-Methyl-enebis(naphthalene-2,1-di-yl)]bis-(-oxymethyl-ene)}di-benzo-nitrile.

Project description:There are two independent mol-ecules in the asymmetric unit of the title compound, C(37)H(26)N(2)O(2). The crystal structure is stabilized by a weak intra-molecular hydrogen bond as well as C-H⋯π inter-actions.

| S-EPMC2960981 | biostudies-literature

(Z)-?-Boryl-crotylboron reagents via Z-selective alkene isomerization and application to stereoselective syntheses of (E)-?-boryl-syn-homoallylic alcohols.

Project description:Stereoselective synthesis of (Z)-?-boryl-crotylboronate is developed. Ni-catalyzed Z-selective alkene isomerization of ?-boryl substituted homoallylboronate provided the targeted (Z)-crotylboronate with high selectivity. Stereoselective addition of the novel crotylboron reagent to aldehydes gave (E)-?-boryl-substituted syn-homoallylic alcohols with excellent diastereoselectivities. The vinyl boronate unit in the products can be directly used for a subsequent C-C bond-forming transformation as illustrated in the synthesis of the C1-7 fragment of the natural products nannocystin A and nannocystin Ax.

| S-EPMC6432281 | biostudies-literature

Phosphotyrosine isosteres: past, present and future.

Project description:Tyrosine phosphorylation is a critical component of signal transduction for multicellular organisms, particularly for pathways that regulate cell proliferation and differentiation. While tyrosine kinase inhibitors have become FDA-approved drugs, inhibitors of the other important components of these signaling pathways have been harder to develop. Specifically, direct phosphotyrosine (pTyr) isosteres have been aggressively pursued as inhibitors of Src homology 2 (SH2) domains and protein tyrosine phosphatases (PTPs). Medicinal chemists have produced many classes of peptide and small molecule inhibitors that mimic pTyr. However, balancing affinity with selectivity and cell penetration has made this an extremely difficult space for developing successful clinical candidates. This review will provide a comprehensive picture of the field of pTyr isosteres, from early beginnings to the current state and trajectory. We will also highlight the major protein targets of these medicinal chemistry efforts, the major classes of peptide and small molecule inhibitors that have been developed, and the handful of compounds which have been tested in clinical trials.

| S-EPMC7233463 | biostudies-literature

Approaching a "Naked" Boryl Anion: Amide Metathesis as a Route to Calcium, Strontium, and Potassium Boryl Complexes.

Project description:Amide metathesis has been used to generate the first structurally characterized boryl complexes of calcium and strontium, {(Me3 Si)2 N}M{B(NDippCH)2 }(thf)n (M=Ca, n=2; M=Sr, n=3), through the reactions of the corresponding bis(amides), M{N(SiMe3 )2 }2 (thf)2 , with (thf)2 Li- {B(NDippCH)2 }. Most notably, this approach can also be applied to the analogous potassium amide K{N(SiMe3 )2 }, leading to the formation of the solvent-free borylpotassium dimer [K{B(NDippCH)2 }]2 , which is stable in the solid state at room temperature for extended periods (48 h). A dimeric structure has been determined crystallographically in which the K+ cations interact weakly with both the ipso-carbons of the flanking Dipp groups and the boron centres of the diazaborolyl heterocycles, with K⋅⋅⋅B distances of >3.1 Å. These structural features, together with atoms in molecules (QTAIM) calculations imply that the boron-containing fragment closely approaches a limiting description as a "free" boryl anion in the condensed phase.

| S-EPMC7894291 | biostudies-literature

Orthogonal reactivity in boryl-substituted organotrifluoroborates.

Project description:A method was developed for the hydroboration of alkenyl-containing organotrifluoroborates to generate dibora intermediates. The reactivity differences between organotrifluoroborates and trialkylboranes facilitated the cross-coupling of the borane moiety of these intermediates in a highly chemoselective fashion with aryl halides, leaving the trifluoroborate intact for subsequent transformation. A one-pot hydroboration/two-directional cross-coupling sequence was also demonstrated, providing the fully elaborated products in good yields. These conditions were also amenable in the cross-coupling of trialkylboranes to halo-containing organotrifluoroborates. The stability of the trifluoroborate moiety to these conditions allows simple and efficient strategies for complex molecule construction.

| S-EPMC2645949 | biostudies-literature

Bis[3-(dihydroxy-boryl)anilinium] sulfate.

Project description:In the title compound, 2C(6)H(9)BNO(2) (+)·SO(4) (2-), the dihydroxy-boryl group of one of the two independent boronic acid mol-ecules participates in (B)O-H?O(B) and N-H?O(B) hydrogen bonds, while the second is involved mainly in the formation of the charge-assisted heterodimeric synthon -B(OH)(2)?(-)O(2)SO(2) (-). These aggregates are further connected through N-H?O(sulfate) inter-actions, forming a complex three-dimensional hydrogen-bonded network.

| S-EPMC2979015 | 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