608534-41-4

Usage

Uses

Used in Organic Synthesis:
2-(9H-CARBAZOLYL)ETHYLBORONIC ACID PINACOL ESTER is used as a reagent in organic synthesis for the formation of carbon-carbon bonds. Its unique structure and reactivity make it a valuable tool in constructing complex molecules and materials with diverse applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-(9H-CARBAZOLYL)ETHYLBORONIC ACID PINACOL ESTER is used as a building block for the preparation of various functional materials and pharmaceuticals. Its versatility in organic synthesis allows for the development of new drugs and therapeutic agents.
Used in Suzuki-Miyaura Cross-Coupling Reactions:
2-(9H-CARBAZOLYL)ETHYLBORONIC ACID PINACOL ESTER is used as a coupling partner in Suzuki-Miyaura cross-coupling reactions, a fundamental method in organic synthesis. This reaction allows for the formation of carbon-carbon bonds, enabling the creation of a wide range of organic compounds and materials.
Used in Material Science:
In the field of material science, 2-(9H-CARBAZOLYL)ETHYLBORONIC ACID PINACOL ESTER is used as a building block for the development of functional materials with specific properties. Its reactivity and structure contribute to the creation of materials with potential applications in various industries, such as electronics, energy, and nanotechnology.

InChI:InChI=1/C20H24BNO2/c1-19(2)20(3,4)24-21(23-19)13-14-22-17-11-7-5-9-15(17)16-10-6-8-12-18(16)22/h5-12H,13-14H2,1-4H3

Upstream product

• 1484-13-5 9-vinyl-9H-carbazole 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 86-74-8 9H-carbazole 
• 74-95-3 1,1-dibromomethane 
• 73183-34-3 bis(pinacol)diborane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 

Downstream Products

• 1484-14-6 2-carbazol-9-yl-ethanol 

Relevant academic research and scientific papers

Aza-Matteson Reactions via Controlled Mono-and Double-Methylene Insertions into Nitrogen-Boron Bonds

Boron-homologation reactions represent an efficient and programmable approach to prepare alkylboronates, which are valuable and versatile synthetic intermediates. The typical boron-homologation reaction, also known as the Matteson reaction, involves formal carbenoid insertions into C-B bonds. Here we report the development of aza-Matteson reactions via carbenoid insertions into the N-B bonds of aminoboranes. By changing the leaving groups of the carbenoids and altering Lewis acid activators, selective mono- and double-methylene insertions can be realized to access various α- and β-boron-substituted tertiary amines, respectively, from common secondary amines. The derivatization of complex amine-containing bioactive molecules, diverse functionalization of the boronate products, and sequential insertions of different carbenoids have also been achieved.

Recyclable Copper Nanoparticles-Catalyzed Hydroboration of Alkenes and β-Borylation of α,β-Unsaturated Carbonyl Compounds with Bis(Pinacolato)Diboron

Nano-ferrite-supported Cu nanoparticles (Fe-dopamine-Cu NPs) catalyzed anti-Markovnikov-selective hydroboration of alkenes with B2pin2 is reported under mild reaction conditions. This protocol can be applied to a broad range of substrates with high functional group compatibility. In addition, we demonstrated the use of Fe-dopamine-Cu NPs as a catalyst for the β-borylation of α,β-unsaturated ketones and ester, providing alkylboronate esters in up to 98% yield. Reuse of the magnetically recyclable catalyst resulted in no significant loss of activity in up to five reaction runs for both systems. (Figure presented.).

Hydroboration of Terminal Alkenes and trans-1,2-Diboration of Terminal Alkynes Catalyzed by a Manganese(I) Alkyl Complex

A MnI-catalyzed hydroboration of terminal alkenes and a 1,2-diboration of terminal alkynes with pinacolborane (HBPin) is described. For alkenes, anti-Markovnikov hydroboration takes place; for alkynes the reaction proceeds with excellent trans-1,2-selectivity. The most active pre-catalyst is bench-stable alkyl bisphosphine MnI complex fac-[Mn(dippe)(CO)3(CH2CH2CH3)]. The catalytic process is initiated by migratory insertion of a CO ligand into the Mn–alkyl bond to yield an acyl intermediate, which undergoes B?H bond cleavage of HBPin (for alkenes) and rapid C?H bond cleavage (for alkynes), forming the active MnI boryl and acetylide catalysts [Mn(dippe)(CO)2(BPin)] and [Mn(dippe)(CO)2(C≡CR)], respectively. A broad variety of aromatic and aliphatic alkenes and alkynes was efficiently and selectively borylated. Mechanistic insights are provided based on experimental data and DFT calculations revealing that an acceptorless reaction is operating involving dihydrogen release.

Synthesis and Catalytic Reactivity of Cobalt Pincer Nitrosyl Hydride Complexes

The synthesis, characterization, and catalytic activity of low-spin {CoNO}8 pincer complexes of the type [Co(PCP)(NO)(H)] are described. These compounds are obtained either by reacting [Co(PCP)(κ2-BH4)] with NO and Et3N or, alternatively, by reacting [Co(

Markovnikov-Selective Co(I)-Catalyzed Hydroboration of Vinylarenes and Carbonyl Compounds

An NHC-supported Co(I) catalyst has been developed for selective Markovnikov hydroboration of vinylarenes under mild reaction conditions. The hydroboration allows highly selective synthesis of a wide range of secondary and tertiary alkyl boronates in exce

Insights into a Chemoselective Cobalt Catalyst for the Hydroboration of Alkenes and Nitriles

A chemoselective hydroboration protocol with terminal alkene substrates is reported using an electron-rich, low-valent cobalt pincer compound. The process is catalytic and leads to exclusive formation of anti-Markovnikov products, tolerating amino groups, esters, epoxides, ketones, and other functionalities. The protocol was successfully extended toward the hydroboration of nitriles, generating the corresponding amines in moderate to good yields. Labeling studies with deuterated pinacolborane gave insights into the mechanism, establishing the intermediacy of a cobalt hydride, as well as an insertion, β-hydride elimination, and alkene isomerization pathway. These insights provide a rationale for the observed regioselectivity and allow us to propose a catalytic mechanism.

A cobalt-catalyzed alkene hydroboration with pinacolborane

An extremely efficient cobalt catalyst for the hydroboration of both vinylarenes and aliphatic α-olefins with pinacolborane is described, providing the anti-Markovnikov products with excellent regio- and chemoselectivity, broad functional-group tolerance,

The transition metal catalyzed hydroboration of enamines

The addition of catecholborane (HBcat, cat = 1,2-O2C6H4) to 9-vinylcarbazole can give either the branched or linear hydroboration product depending upon the judicious choice of metal catalyst used in these reactions. Analo

Di(isopropylprenyl)borane: A new hydroboration reagent for the synthesis of alkyl and alkenyl boronic acids

The best of the old: The new hydroboration reagent 1 combines the selectivity of disiamylborane (2) with the reactivity towards carbonyls of allyl boranes 3. Conventional oxidative workup conditions are avoided, as facile hydrolysis in protic media provides the corresponding boronic acids with up to 99% anti-Markovnikov selectivities. A one-pot hydroboration/ Suzuki-Miyaura protocol adds to the synthetic value of 1.