287944-13-2

Usage

Uses

Used in Organic Synthesis:
1-Cyclohepten-1yl boronic acid pinacol ester is used as a reagent for the formation of carbon-carbon and carbon-heteroatom bonds in organic synthesis. Its high stability and reactivity make it a valuable building block in the development of complex organic molecules.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 1-Cyclohepten-1yl boronic acid pinacol ester is used as a key intermediate in the synthesis of various drug molecules. Its versatility in forming different types of chemical bonds allows for the creation of diverse and functionalized pharmaceutical compounds.
Used in Agrochemical Synthesis:
1-Cyclohepten-1yl boronic acid pinacol ester is also utilized in the agrochemical industry for the synthesis of various agrochemical products. Its ability to form stable bonds with other molecules contributes to the development of effective and stable agrochemicals.
Used in Materials Science:
In the field of materials science, 1-Cyclohepten-1yl boronic acid pinacol ester is employed in the synthesis of advanced materials with specific properties. Its reactivity and stability make it suitable for the development of materials with tailored characteristics for various applications.
Used in Cross-Coupling Reactions:
1-Cyclohepten-1yl boronic acid pinacol ester is used as a reactant in cross-coupling reactions, a widely used method in organic chemistry for the formation of carbon-carbon bonds. Its participation in these reactions contributes to the efficient synthesis of complex organic molecules with desired structural features.
Overall, 1-Cyclohepten-1yl boronic acid pinacol ester is a versatile and efficient compound in the field of organic chemistry, with applications spanning across various industries, including pharmaceuticals, agrochemicals, and materials science. Its high stability and reactivity make it an indispensable tool in the synthesis of complex and functionalized chemical structures.

Upstream product

• 28075-51-6 cyclohept-1-en-1-yl trifluoromethanesulfonate 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 56382-69-5 cycloheptanone p-tolylsulfonylhydrazone 
• 628-92-2 Cycloheptene 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 502-42-1 cycloheptanone 
• 22081-48-7 (cyclohept-1-en-1-yloxy)(trimethyl)silane 

Downstream Products

• 1445871-61-3 C₂₀H₂₁NO₂ 
• 835882-35-4 (Z)-cyclohept-1-en-1-ylboronic acid 
• 7257-25-2 7,8,9,10-tetrahydrocyclohepta[b]indol-6(5H)-one 

Relevant academic research and scientific papers

Copper-catalyzed tri- or tetrafunctionalization of alkenylboronic acids to prepare tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles

We describe a cascade strategy for tri- or tetrafunctionalization of alkenylboronic acids to prepare diverse tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles in good yields withN-hydroxybenzotriazin-4-one (HOOBT) and arylhydrazines as oxygen and nitrogen sources, respectively. Mechanistic studies reveal that the domino reaction undergoes the copper-catalyzed Chan-Lam reaction, [2,3]-rearrangement, nucleophilic substitution, oxidation and sequential [3,3]-rearrangement over five steps in a one-pot reaction. The reaction shows a broad substrate scope and tolerates a wide range of functional groups. More importantly, the reaction is easily performed at gram scales and the product is purified by simple extraction, washing, and recrystallization without flash column chromatography. The present protocol features easily available starting materials, high site-marked functionalization, five-step cascade in one pot, multiple C-C/C-O/C-N bond formation, and diversity of indole motifs.

Alkenyl boron compound and preparation method and application thereof

The invention discloses an alkenyl boron compound and a preparation method and application thereof. The preparation method comprises the following steps: in a protective atmosphere, enabling a uniformly mixed reaction system containing a lithium enol reag

Development and Mechanistic Studies of Iron-Catalyzed Construction of Csp2-B Bonds via C-O Bond Activation

Herein we describe an iron-catalyzed borylation of alkenyl and aryl carbamates through the activation of a C-O bond. This protocol exhibits high efficiency, a broad substrate scope, and the late-stage borylation of biorelevant compounds, thus providing potential applications in medicinal chemistry. Moreover, this method enables orthogonal transformations of phenol derivatives and also offers good opportunities for the synthesis of multisubstituted arenes. Preliminary mechanistic studies suggest that a FeII/FeIII catalytic cycle via a radical pathway might be involved in the reaction.

Stereoselective Synthesis of Trisubstituted Vinylboronates from Ketone Enolates Triggered by 1,3-Metalate Rearrangement of Lithium Enolates

An unprecedented stereoselective synthesis of trisubstituted vinylboronates is reported to proceed by direct borylation of lithium ketone enolates under transition-metal-free conditions. The stereospecific C?O borylation of lithium enolates was triggered by a carbonyl-induced 1,3-metalate rearrangement via a C-bound boron enolate. DFT calculations and control experiments revealed that the stereoselectivity is controlled by sterics. A variety of stereospecific trisubstituted vinylboronates, together with several tetrasubstituted vinylboronates, were conveniently synthesized with the newly developed methodology. Based on the transformation of stereospecific vinylboronate, a single isomer of Dienestrol was efficiently obtained.

Interrupted fischer-indole intermediates via oxyarylation of alkenyl boronic acids

The oxyarylation of alkenyl boronic acids with N-arylbenzhydroxamic acids has been achieved under both copper-mediated and copper-catalyzed conditions to provide access to interrupted Fischer-indole intermediates. This transformation is believed to proceed through a copper-promoted C-O bond forming event followed by a [3,3] rearrangement. The scope of the method is described and mechanistic experiments are discussed.

PSiP-pincer type palladium-catalyzed dehydrogenative borylation of alkenes and 1,3-Dienes

Dehydrogenative borylation of alkenes and 1,3-dienes was realized by carrying out the reaction in the presence of bis(pinacolato)diboron (B2pin2) and a catalytic amount of PSiP-pincer palladium complex. This protocol has the following notable features. 1)

Rhodium-catalyzed dehydrogenative borylation of cyclic alkenes

A rhodium-catalyzed dehydrogenative borylation of cyclic alkenes is described. This reaction provides direct access to cyclic 1-alkenylboronic acid pinacol esters, useful intermediates in organic synthesis. Suzuki-Miyaura cross-coupling applications are also presented. The Royal Society of Chemistry 2010.

Selective C-H borylation of alkenes by palladium pincer complex catalyzed oxidative functionalization

(Figure Presented) The C-H borylation of simple alkenes catalyzed by palladium pincer complex 1 was performed in the presence of hypervalent iodine and bis(pinacolato)diboron compounds. The borylation reaction probably occurs by a PdIIPdIVoxidationdiboronate transmetalation sequence. TFA = trifluoroacetate.

Catalytic asymmetric synthesis of palmerolide a via organoboron methodology

(Chemical Equation Presented) A catalytic enantioselective synthesis of the antimelanoma marine natural product (-)-palmerolide A was accomplished using a longest sequence of 21 steps and without resorting to stoichiometric chiral auxiliaries or the chiral pool. The right half was constructed with a new variant of the Claisen-Ireland rearrangement exploiting an alkenylboronate as a masked hydroxyl. The left half featured the first application of a diol·SnCl4-catalyzed enantioselective crotylboration in the context of a complex target. This distinct strategy could pave the way to the design of simplified analogues of palmerolide.

Palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron with 1-alkenyl halides or triflates: Convenient synthesis of unsymmetrical 1,3-dienes via the borylation-coupling sequence

The synthesis of 1-alkenylboronic acid pinacol esters via a palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron (pin2B2, pin = Me4C2O2) with 1-alkenyl halides or triflates was carrie