Transition Metal Free Synthesis of Heterobiaryls Through 1,2-Migration of Boronate Complex.
@article{Paul2019TransitionMF, title={Transition Metal Free Synthesis of Heterobiaryls Through 1,2-Migration of Boronate Complex.}, author={Swagata Paul and Kanak Kanti Das and Samir Manna and Santanu Panda}, journal={Chemistry}, year={2019} }
The synthesis of a diverse range of heterobiaryl has been achieved via a transition metal free sp 2 -sp 2 cross coupling strategy using lithiated heterocycle, aryl or heteroaryl boronic ester and an electrophilic halogen source. The construction of heterobiaryls was carried out through electrophilic activation of the aryl-heteroaryl boronate complex which triggered 1,2-migration from boron to the carbon atom. Subsequent oxidation of the intermediate boronic ester afforded heterobiaryls in good…
11 Citations
Development of Methods to the Synthesis of β‐Boryl Acyls, Imines and Nitriles
- ChemistryChemical record
- 2022
Organoboron compounds are highly important and versatile synthetic intermediates for the preparation of a wide range of organic molecules. Organoboron compounds have drawn significant attention among…
Synthesis of Ketones by C−H Functionalization of Aldehydes with Boronic Acids under Transition‐Metal‐Free Conditions
- Chemistry
- 2021
A method for the synthesis of ketones from aldehydes and boronic acids via a transition-metal-free C-H functionalization reaction is reported. The method employs nitrosobenzene as a reagent to drive…
Transition metal catalyzed asymmetric multicomponent reactions of unsaturated compounds using organoboron reagents.
- ChemistryChemical communications
- 2020
This review will discuss the merits and scope of multicomponent strategies based on their difference in the reaction mechanism and transition metals involved.
Transition‐Metal‐Free Oxidative Cross‐Coupling of Tetraarylborates to Biaryls Using Organic Oxidants
- ChemistryAngewandte Chemie
- 2020
Transition‐metal‐free catalytic oxidative ligand cross‐coupling of tetraarylborates is unprecedented and the introduced method provides access to various biaryl and heterobiaryl systems.
N-Methylphenothiazine S-Oxide Enabled Oxidative C(sp2)-C(sp2) Coupling of Boronic Acids with Organolithiums via Phenothiaziniums.
- ChemistryOrganic letters
- 2021
A transition-metal-free oxidative C(sp2)-C(Sp2) coupling of readily available boronic acids and organolithiums via phenothiazinium ions via PTZSO is reported, which allows efficient conversion of borony acids to phenothia ions.
Room-Temperature Palladium(II)-Catalyzed Direct 2-Arylation of Indoles with Tetraarylstannanes
- Chemistry, Biology
- 2020
A palladium(II)-catalyzed direct 2-arylation of indoles by tetraarylstannanes with oxygen (balloon) as the oxidant at room temperature has been developed, providing a practical and efficient catalytic protocol for accessing 2-arylindoles.
Synthesis and reactivity of alkynyl boron compounds.
- ChemistryOrganic & biomolecular chemistry
- 2021
In this review, the advancement of research on alkynyl boron compounds is summarized, highlighting their importance in the synthesis of valuable compounds.
Functionalization of Heterocycles Through 1,2-Metallate Rearrangement of Boron Ate Complex.
- ChemistryChemistry
- 2020
This minireview highlights the methods known till date for the synthesis of heteroaryls using 1,2-migration of boronate complex in a chronological manner.
Five-membered ring systems: thiophenes and selenium/tellurium analogues and benzo analogues
- ChemistryProgress in Heterocyclic Chemistry
- 2021
References
SHOWING 1-10 OF 50 REFERENCES
Heterobiaryl synthesis by contractive C–C coupling via P(V) intermediates
- ChemistryScience
- 2018
Phosphorus proves a versatile coupling agent for nitrogen heterocycles in pharmaceutical and agrochemical synthesis and enables convergent coupling of drug fragments and late-stage heteroarylation of pharmaceuticals.
Tandem Allylation/1,2-Boronate Rearrangement for the Asymmetric Synthesis of Indolines with Adjacent Quaternary Stereocenters.
- Chemistry, BiologyJournal of the American Chemical Society
- 2018
A novel radical-mediated annulation provides polycyclic products with high enantio- and diastereoselectivity in the specific case of methyl-vinyl ketone as well as a stepwise allylation-aryl/alkyl migration.
Direct catalytic cross-coupling of organolithium compounds
- ChemistryNature Chemistry
- 2013
A general and selective palladium-catalysed cross-coupling of aryl- and alkenyl-bromides with a wide range of alkyl-, aryL- and heteroaryl-lithium reagents is reported, which avoids the notorious lithium–halogen exchange and homocoupling side-reactions commonly associated with these extremely reactive organometallic compounds.
Transition-Metal-Free Suzuki-Type Cross-Coupling Reaction of Benzyl Halides and Boronic Acids via 1,2-Metalate Shift.
- ChemistryJournal of the American Chemical Society
- 2018
A new approach that uses a single organic sulfide catalyst to activate both C(sp3) halides and arylboronic acids via a zwitterionic boron "ate" intermediate is described, demonstrating orthogonal chemoselectivity in the streamlined synthesis of highly functionalized diaryl methane scaffolds using multi-halogenated substrates.
Development of Enantiospecific Coupling of Secondary and Tertiary Boronic Esters with Aromatic Compounds
- ChemistryJournal of the American Chemical Society
- 2016
This work reasoned that subsequent addition of an oxidant or an electrophile would remove an electron from the aromatic ring or react in a Friedel–Crafts-type manner, respectively, generating a cationic species, which would trigger 1,2-migration of the boron substituent, creating the new C–C bond.
Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds
- Chemistry
- 1995
B. Other Catalyti; Process by Transition-Metal Complexes IV. Cross-Coupling Reaction A. Coupling of 1 -Alkenylboron Derivatives: Synthesis of Conjugated Dienes 6. Coupling of Arylboron Derivatives:…
Enantiospecific sp(2)-sp(3) coupling of secondary and tertiary boronic esters.
- ChemistryNature chemistry
- 2014
It is discovered that enantioenriched secondary and tertiary boronic esters can be coupled to electron-rich aromatics with essentially complete enantiospecificity and should find considerable application, particularly in the pharmaceutical industry.
50 Years of Zweifel Olefination: A Transition-Metal-Free Coupling
- ChemistrySynthesis
- 2017
The Zweifel olefination is a powerful method for the stereoselective synthesis of alkenes. The reaction proceeds in the absence of a transition-metal catalyst, instead taking place by iodination of…
Fine-tuning the nucleophilic reactivities of boron ate complexes derived from aryl and heteroaryl boronic esters.
- ChemistryAngewandte Chemie
- 2015
Boron ate complexes derived from thienyl and furyl boronic esters and aryllithium compounds have been isolated and characterized by X-ray crystallography and the neopentyl and ethylene glycol derivatives were found to be 10(4) times more reactive than the pinacol and catechol derivatives.
Catalytic conjunctive cross-coupling enabled by metal-induced metallate rearrangement
- ChemistryScience
- 2016
It is demonstrated that vinyl boronic ester ate complexes, prepared by combining organoboronates and organolithium reagents, engage in palladium-induced metallate rearrangement wherein 1,2-migration of an alkyl or aryl group from boron to the vinyl α-carbon occurs concomitantly with C–Pd σ-bond formation.