cas 141091-37-4, Cyclohexene-1-boronic acid pinacol ester

Articles about 141091-37-4Total 36 be found

Article title
Article abstract
Author
Journal number and time
Download

Copper(i)-catalysed regio- and diastereoselective intramolecular alkylboration of terminal allenes: via allylcopper(i) isomerization
We report the first copper(i)-catalysed intramolecular alkylboration of terminal allenes with an alkyl halide moiety. The reaction provides alkenylboronates bearing a four-membered ring structure with high regio- and diastereocontrol. A possible reaction mechanism is proposed, involving the facile isomerization of an allylcopper(i) intermediate. A DFT study explains the experimental regio- and diastereoselectivity.
Ozawa, Yu,Iwamoto, Hiroaki,Ito, Hajime
p. 4991 - 4994
(2018)
Read Online

Synthesis of alkenylboronates via palladium-catalyzed borylation of alkenyl triflates (or Iodides) with pinacolborane
Various alkenyl iodides and triflates were borylated with pinacolborane in the presence of Et3N and a catalytic amount of PdCl2(dppf) and AsPh3 to afford the corresponding alkenylboronates in good yields.
Murata, Miki,Oyama, Takashi,Watanabe, Shinji,Masuda, Yuzuru
p. 778 - 780
(2000)
Read Online

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.
Selander, Nicklas,Willy, Benjamin,Szabo, Kaiman J.
p. 4051 - 4053
(2010)
Read Online

Substituted Tetraethynylethylene–Tetravinylethylene Hybrids
A general synthetic approach to molecular structures that are hybrids of tetraethynylethylene (TEE) and tetravinylethylene (TVE) is reported. The synthesis permits the controlled preparation of many previously inaccessible structures, including examples w
Connor, Kieran P. E.,Horvath, Kelsey L.,Magann, Nicholas L.,Sherburn, Michael S.,Sowden, Madison J.,Westley, Erin
p. 977 - 986
(2022/02/03)

Aluminium-Catalyzed C(sp)?H Borylation of Alkynes
Historically used in stoichiometric hydroalumination chemistry, recent advances have transformed aluminium hydrides into versatile catalysts for the hydroboration of unsaturated multiple bonds. This catalytic ability is founded on the defining reactivity of aluminium hydrides with alkynes and alkenes: 1,2-hydroalumination of the unsaturated π-system. This manuscript reports the aluminium hydride catalyzed dehydroborylation of terminal alkynes. A tethered intramolecular amine ligand controls reactivity at the aluminium hydride centre, switching off hydroalumination and instead enabling selective reactions at the alkyne C?H σ-bond. Chemoselective C?H borylation was observed across a series of aryl- and alkyl-substituted alkynes (21 examples). On the basis of kinetic and density functional theory studies, a mechanism in which C?H borylation proceeds by σ-bond metathesis between pinacolborane (HBpin) and alkynyl aluminium intermediates is proposed.
Willcox, Dominic R.,De Rosa, Daniel M.,Howley, Jack,Levy, Abigail,Steven, Alan,Nichol, Gary S.,Morrison, Carole A.,Cowley, Michael J.,Thomas, Stephen P.
supporting information
p. 20672 - 20677
(2021/08/20)

Rhodium-Catalyzed Deoxygenation and Borylation of Ketones: A Combined Experimental and Theoretical Investigation
The rhodium-catalyzed deoxygenation and borylation of ketones with B2pin2 have been developed, leading to efficient formation of alkenes, vinylboronates, and vinyldiboronates. These reactions feature mild reaction conditions, a broad substrate scope, and excellent functional-group compatibility. Mechanistic studies support that the ketones initially undergo a Rh-catalyzed deoxygenation to give alkenes via boron enolate intermediates, and the subsequent Rh-catalyzed dehydrogenative borylation of alkenes leads to the formation of vinylboronates and diboration products, which is also supported by density functional theory calculations.
Tao, Lei,Guo, Xueying,Li, Jie,Li, Ruoling,Lin, Zhenyang,Zhao, Wanxiang
p. 18118 - 18127
(2020/11/26)

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.
Bi, Hong-Yan,Li, Cheng-Jing,Liang, Cui,Mo, Dong-Liang,Wei, Cui
supporting information
p. 5815 - 5821
(2020/09/21)

Copper-catalyzed cross-coupling of vinyliodonium salts and diboron reagents to generate alkenyl boronic esters
An efficient approach for the synthesis of alkenyl boronic esters through the copper-catalyzed cross-coupling of vinyliodonium salts and diboron reagents is reported. This method is distinguished by its mild conditions and short reaction time of less than
Bao, Robert Li-Yuan,Gan, Shaoyan,Shi, Lei,Zhu, Dan
supporting information
p. 5567 - 5570
(2020/08/21)

Carboboration of Alkynes with Cyclodextrin-Encapsulated N-Heterocyclic Carbene Copper Complexes
The copper-catalyzed carboboration of various alkynes was investigated with a modified N-heterocyclic carbene-capped α-cyclodextrin copper(I) complex in which the reactive copper center is deeply encapsulated in the cyclodextrin (CD) cavity. The methylborylation of terminal alkynes was found to give linear (L) (E)-vinyl boron isomers as the major isomers, as expected from the previously proposed “perpendicular” approach of the alkyne to the Cu–B bond, and methylation of the vinyl boron copper intermediate. Under similar conditions, the intramolecular carboboration reaction with terminal alkynes functionalized by alkyl halides, led to exocyclic vinyl boronate species as the major isomer. However, an endocyclic (Z)-isomer was also observed in some cases. This isomer was not previously observed and is unexpected considering the “classical” mechanism. The direct generation of boron functionalized (Z)-alkenes by carboboration of alkynes is unprecedented.
Wen, Zhonghang,Zhang, Yongmin,Roland, Sylvain,Sollogoub, Matthieu
p. 2682 - 2687
(2019/04/08)

Red phosphorescent compound and organic light emitting diode device using organic light emitting diode
The present invention discloses a organic light emitting diode and an organic light emitting diode device using the organic light emitting diode. The organic light emitting diode having the structuralformula as shown in I, wherein R1, R2, R3 and R4 are independently selected from one of H and C1 to C6 alkyl groups; in the formula (I), a group shown in the specification is selected one the group consisting of a specific alkanedione and a derivative thereof. The organic light emitting diode device includes a positive pole, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer and a negative pole which are sequentially deposited; the organic light emitting diode device comprises the organic light emitting diodeas a dopant. The organic light emitting diode enables the organic light emitting diode device to have high efficiency and high color purity and narrow spectrum.
-
Paragraph 0064; 0065; 0066

(2019/01/24)

Red phosphorescent compound and organic electroluminescence device employing same
The invention discloses a red phosphorescent compound and an organic electroluminescence device employing the same. The structural formula of the red phosphorescent compound is as shown in the description, wherein formula represents formula, and R1, R2, R3 and R4 are independently selected from one of H and C1-C6 alkyl; in the formula (I), formula represents special alkyl diketone and derivativesthereof. The organic electroluminescence device comprises an anode, a hole injection layer, a hole transfer layer, a luminescent layer, an electron transfer layer, an electron injection layer and a cathode which are successively deposited. The organic electroluminescence device comprises the red phosphorescent compound as a doping agent. According to the red phosphorescent compound provided by theinvention, the organic electroluminescence device is high in efficiency, high in color purity and narrow in spectrum.
-
Paragraph 0063-0065

(2019/02/04)

Red phosphorescent compound and organic light emitting diode device using red phosphorescent compound
The present invention discloses a red phosphorescent compound and an organic light emitting diode device using the red phosphorescent compound. The red phosphorescent compound having the structural formula as shown in I, wherein R1, R2, R3 and R4 are independently selected from one of H and C1 to C6 alkyl groups; in the formula (I), a group shown in the specification is selected one the group consisting of a specific alkanedione and a derivative thereof. The organic light emitting diode device includes a positive pole, a hole injecting layer, a hole transporting layer, a light emitting layer,an electron transporting layer, an electron injecting layer and a negative pole which are sequentially deposited; the organic light emitting diode device comprises the red phosphorescent compound as adopant. The red phosphorescent compound enables the organic light emitting diode device to have high efficiency and high color purity and narrow spectrum.
-
Paragraph 0062; 0063; 0064

(2019/01/24)

Red phosphorescent compound and organic electroluminescent device using red phosphorescent compound
The present invention discloses a red phosphorescent compound and an organic electroluminescent device using the red phosphorescent compound. The red phosphorescent compound having the structural formula as shown in I, wherein R1, R2, R3 and R4 are indepe
-
Paragraph 0062; 0063; 0064

(2019/01/24)

Red phosphorescence compounds and organic light-emitting device applying the compounds
Red phosphorescence compounds and an organic light-emitting device applying the compounds are disclosed. The general structure formula of the compounds is shown as I, wherein a structure shown in thedescription represents a structure shown in the descript
-
Paragraph 0052; 0053; 0054; 0055

(2019/03/10)

Red phosphor compound and organic electroluminescence device using same
The invention discloses a red phosphor compound and an organic electroluminescence device using the same. A structural formula of the red phosphor compound is shown as I, wherein an expression formula refers to as follows, R1, R2, R3 and R4 are independen
-
Paragraph 0052; 0053; 0054

(2019/04/06)

Green phosphorescent compound and organic electroluminescence device using green phosphorescent compound
The invention discloses a green phosphorescent compound and an organic electroluminescence device using the green phosphorescent compound. The organic electroluminescence device comprises a positive electrode, a hole injection layer, a hole transmission layer, a luminescent layer, an electron transmission layer, an electron injection layer and a negative electrode in mutually and sequentially deposition; the organic electroluminescence device can use the green phosphorescent compound shown as a formula (I) shown in specification as a doping agent of a luminescent layer; n is 1 or 2. The greenphosphorescent material has the effects of high efficiency, high color purity and narrow optical spectrum.
-
Paragraph 0077-0079

(2019/06/11)

Green phosphorescent compound and organic electroluminescence device using same
The invention discloses a green phosphorescent compound and an organic electroluminescence device using the same. An anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode are sequentially deposited in the organic electroluminescence device. The organic electroluminescent device can use the green phosphorescent compound shown by the formula (I) as shown in the specification as a dopant of the light emitting layer, wherein n is 1 or 2.
-
Paragraph 0078-0080

(2019/06/13)

Green phosphorescent compound and organic electroluminescent device using same
The invention discloses a green phosphorescent compound and an organic electroluminescent device using the same. The organic electroluminescent device includes an anode, a hole injection layer, a holetransport layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode which are sequentially deposited from each other. The organic electroluminescent devicecan use a phosphorescent compound represented by a following formula (1) as a dopant for the light emitting layer, wherein R1, R2, R3, R4, R5, R6, R7, R8 and R9 are each independently substituted orunsubstituted C1-C6 alkyl, C1-C6 alkoxyl, or halogens. The green phosphorescent material has the advantages of high efficiency, high color purity and narrow spectrum effect.
-
Paragraph 0077-0079

(2019/08/12)

Preparation method of allylboronic acid pinacol ester
The invention provides a common preparation method of allylboronic acid pinacol ester. The common preparation method takes aliphatic ketone as a raw material and comprises the following steps: takingaliphatic ketone and p-toluenesulfonohydrazide as raw ma
-
Paragraph 0006

(2019/04/06)

The active metal sodium or lithium quenching method (by machine translation)
This invention claims an active metal sodium or [...] method. In the use of the metal sodium to participate in free radical coupling reaction or metal lithium participation when halogen lithium exchange reaction, reaction to the end of the excess active metal usually security quenching, excessive metal sodium and lithium adopts the halogenated hydrocarbon to process quenching, to avoid using traditional water or mellow quenching when the generation of hydrogen gas, operating the safety factor is increased. The method is simple in operation, the generated coupling alkane does not influence the reaction processing, is suitable for industrial scale production quenching using. (by machine translation)
-
Paragraph 0024

(2019/04/26)

Metal-Free Radical Borylation of Alkyl and Aryl Iodides
A metal-free radical borylation of alkyl and aryl iodides with bis(catecholato)diboron (B2cat2) as the boron source under mild conditions is introduced. The borylation reaction is operationally easy to conduct and shows high functional group tolerance and broad substrate scope. Radical clock experiments and density functional theory calculations provide insights into the mechanism and rate constants for C-radical borylation with B2cat2 are disclosed.
Cheng, Ying,Mück-Lichtenfeld, Christian,Studer, Armido
p. 16832 - 16836
(2018/11/23)

Isonicotinate Ester Catalyzed Decarboxylative Borylation of (Hetero)Aryl and Alkenyl Carboxylic Acids through N-Hydroxyphthalimide Esters
Decarboxylative borylation of aryl and alkenyl carboxylic acids with bis(pinacolato)diboron was achieved through N-hydroxyphthalimide esters using tert-butyl isonicotinate as a catalyst under base-free conditions. A variety of aryl carboxylic acids possessing different functional groups and electronic properties can be smoothly converted to aryl boronate esters, including those that are difficult to decarboxylate under transition-metal catalysis, offering a new method enabling use of carboxylic acid as building blocks in organic synthesis. Mechanistic analysis suggests the reaction proceeds through coupling of a transient aryl radical generated by radical decarboxylation with a pyridine-stabilized persistent boryl radical. Activation of redox active esters may proceed via an intramolecular single-electron-transfer (SET) process through a pyridine-diboron-phthalimide adduct and accounts for the base-free reaction conditions.
Cheng, Wan-Min,Shang, Rui,Zhao, Bin,Xing, Wei-Long,Fu, Yao
p. 4291 - 4294
(2017/08/23)

Pyridine-catalyzed radical borylation of aryl halides
A pyridine-catalyzed transition-metal-free borylation reaction of haloarenes has been developed based on the selective cross-coupling of an aryl radical and a pyridine-stabilized boryl radical. Arylboronates were produced from haloarenes under mild conditions. This borylation reaction features a broad substrate scope, operational simplicity, and gram-scale synthetic ability.
Zhang, Li,Jiao, Lei
supporting information
p. 607 - 610
(2017/05/15)

Preparation method of aryl borate ester and allyl borate ester
The invention discloses a preparation method of aryl borate ester and allyl borate ester. The method comprises the following step: under the catalytic action of pyridine or a derivative thereof, carrying out 1) or 2) to obtain substituted boric acid ester shown as a formula I-1 or a formula I-2: 1) a reaction of a halide, bi-boric acid ester and alkoxide; 2) a reaction of a halide and a bi-boric acid ester-alkoxide complex. The method is an efficient preparation method of the aryl borate ester and the allyl borate ester. In the preparation method provided by the invention, the inexpensive pyridine or the derivative thereof is taken as a catalyst instead of a transition metal catalyst, the reaction conditions are mild, the reaction yield is high, residues of trace transition metal in a boronation product are avoided, and the cost of an aryl and allyl borate ester synthesis reaction is lowered.
-
Paragraph 0083-0087

(2017/07/12)

Gold(I) carbenes by retro-buchner reaction: Generation and fate
The fate of the aryl gold(I) carbenes generated by retro-Buchner reaction of ortho-substituted 7-aryl-1,3,5-cycloheptatrienes is dependent on the constitution of the ortho substituent. Indenes and fluorenes are obtained by intramolecular reaction of highly electrophilic gold(I) carbenes with alkenes and arenes. According to density functional theory calculations, the gold-catalyzed retro-Buchner process occurs stepwise, although the two carbon-carbon cleavages occur on a rather flat potential energy surface.
Wang, Yahui,McGonigal, Paul R.,Herle, Bart,Besora, Maria,Echavarren, Antonio M.
supporting information
p. 801 - 809
(2014/02/14)

Highly enantioselective Rh-Catalyzed Alkenylation of imines: Synthesis of Chiral Allylic Amines via Asymmetric addition of Potassium Alkenyltrifluoroborates to N-Tosyl imines
For the first time, simple N-tosyl aryl aldimines, prepared from the condensation of tosyl amide and aromatic aldehydes, can be used as substrates in the rhodium catalyzed 1,2- addition reaction using alkenylboron nucleophiles. In the presence of 1.5 mol % of [RhCl(1e)]2, enantioselective addition of various potassium alkenyltrifluoroborates to aryl aldimines furnished the corresponding chiral allylic amines in 73-96% yield and 72->99.5% ee. Notably, this method efficiently provides the di-, tri-, and tetrasubstituted allylic N-tosyl amines with high asymmetric induction.
Gopula, Balraj,Chiang, Chien-Wei,Lee, Way-Zen,Kuo, Ting-Shen,Wu, Ping-Yu,Henschke, Julian P.,Wu, Hsyueh-Liang
supporting information
p. 632 - 635
(2014/04/03)

Stereoselective formation of trisubstituted vinyl boronate esters by the acid-mediated elimination of α-hydroxyboronate esters
The copper-catalyzed diboration of ketones followed by an acid-catalyzed elimination leads to the formation of 1,1-disubstituted and trisubstituted vinyl boronate esters with moderate to good yields and selectivity. Addition of tosic acid to the crude diboration products provides the corresponding vinyl boronate esters upon elimination. The trisubstituted vinyl boronate esters are formed as the (Z)-olefin isomer, which was established by subjecting the products to a Suzuki-Miyaura coupling reaction to obtain alkenes of known geometry.
Guan, Weiye,Michael, Alicia K.,McIntosh, Melissa L.,Koren-Selfridge, Liza,Scott, John P.,Clark, Timothy B.
p. 7199 - 7204
(2014/08/18)

Highly selective bis(imino)pyridine iron-catalyzed alkene hydroboration
Bis(imino)pyridine iron dinitrogen complexes have been shown to promote the anti-Markovnikov catalytic hydroboration of terminal, internal, and geminal alkenes with high activity and selectivity. The isolated iron dinitrogen compounds offer distinct advan
Obligacion, Jennifer V.,Chirik, Paul J.
supporting information
p. 2680 - 2683
(2013/07/19)

Rhodium-NHC complexes mediate diboration versus dehydrogenative borylation of cyclic olefins: A theoretical explanation
In rhodium catalysed borylation of cyclic olefins, the synergy between bidentate NHC ligands, that modify cationic Rh(i) species, and the use of non-polar solvents, such as cyclohexane, is the key factor to favour a less energetically demanding route towards the formation of diborated products versus allyl boronate esters.
Pubill-Ulldemolins, Cristina,Poyatos, MacArena,Bo, Carles,Fernandez, Elena
supporting information
p. 746 - 752
(2013/02/23)

Exceptionally selective catalytic hydrogenation of alkene with pinacolborane
Abstract: The catalytic hydrogenation of model alkene - cyclohexene with the use of pinacolborane is reported along with the characterization of various side products. The non-standard hydrogenation product was obtained in high yield and purity under very
Niziol, Joanna,Ruman, Tomasz
experimental part
p. 257 - 262
(2012/08/08)

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.
Kondoh, Azusa,Jamison, Timothy F.
p. 907 - 909
(2010/06/12)

Functionalization of unactivated alkenes through iridium-catalyzed borylation of carbon-hydrogen bonds. Mechanism and synthetic applications
(Chemical Equation Presented) This paper describes an efficient carbon-carbon bond formation reaction, which is based on carbon-hydrogen bond functionalization of unactivated alkenes. This process is based on in situ generation of allylic and vinylic boronates by iridium-catalyzed borylation of alkenes followed by carbon-carbon bond formation reactions. The selectivity of the carbon-hydrogen bond functionalization can be efficiently controlled for cyclic alkenes. By using additives, such as methylimidazole and DBU, the iridium-catalyzed borylation led to formation of allyl boronates, which reacted with aldehydes in a one-pot sequence affording stereodefined homoallylic alcohols. Cycloalkenes without additives aswell as acyclic substrates gave vinylic boronates, which were coupled with organohalides in a Suzuki-Miyaura sequence. By this process allylic and vinylic silabutadiene derivatives can be prepared from allylsilanes with excellent regio- and stereoselectivity. The mechanism of the carbon-hydrogen bond functionalization based on the borylation reaction was explored by isotope labeling experiments, measuring the kinetic isotope effect and study of the effects of the additives on the selectivity of the process. It was concluded that the reactions proceed via a dehydrogenative borylationmechanism,which shows analogous features with the palladium-catalyzed Heck coupling reaction.
Olsson, Vilhelm J.,Szabo, Kalman J.
supporting information; body text
p. 7715 - 7723
(2010/02/28)

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
Takagi, Jun,Takahashi, Kou,Ishiyama, Tatsuo,Miyaura, Norio
p. 8001 - 8006
(2007/10/03)

Structure-activity relationships of a series of pyrrolo[3,2-d]pyrimidine derivatives and related compounds as neuropeptide Y5 receptor antagonists
Neuropeptide Y (NPY) has been shown to play an important role in the regulation of food intake and energy balance. Pharmacological data suggests that the Y5 receptor subtype contributes to the effects of NPY on appetite, and therefore a Y5 antagonist might be a useful therapeutic agent for the treatment of obesity. In attempts to identify potential Y5 antagonists, a series of pyrrolo[3,2-d]pyrimidine derivatives was prepared and evaluated for their ability to bind to Y5 receptors in vitro. We report here the synthesis and initial structure-activity relationship investigations for this class of compounds. The target compounds were prepared by a variety of synthetic routes designed to modify both the substitution and the heterocyclic core of the pyrrolo[3,2-d]pyrimidine lead 1. In addition to identifying several potent Y5 antagonists for evaluation as potential antiobesity agents, a pharmacophore model for the human Y5 receptor is presented.
Norman,Chen,Chen,Fotsch,Hale,Han,Hurt,Jenkins,Kincaid,Liu,Lu,Moreno,Santora,Sonnenberg,Karbon
p. 4288 - 4312
(2007/10/03)

Synthesis of 1-alkenylboronic esters via palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron with 1-alkenyl halides and triflates
The synthesis of 1-alkenylboronic acid pinacol esters via the palladium-catalyzed cross-coupling reaction of 1-alkenyl halides or triflates with bis(pinacolato)diboron [(Me4C2O2)B-B(O2C2Me 4/sub
Takahashi, Kou,Takagi, Jun,Ishiyama, Tatsuo,Miyaura, Norio
p. 126 - 127
(2007/10/03)