cas 73852-88-7, 4-Iodobenzeneboronic acid pinacol ester, 97%

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Light- and Manganese-Initiated Borylation of Aryl Diazonium Salts: Mechanistic Insight on the Ultrafast Time-Scale Revealed by Time-Resolved Spectroscopic Analysis
Manganese-mediated borylation of aryl/heteroaryl diazonium salts emerges as a general and versatile synthetic methodology for the synthesis of the corresponding boronate esters. The reaction proved an ideal testing ground for delineating the Mn species responsible for the photochemical reaction processes, that is, involving either Mn radical or Mn cationic species, which is dependent on the presence of a suitably strong oxidant. Our findings are important for a plethora of processes employing Mn-containing carbonyl species as initiators and/or catalysts, which have considerable potential in synthetic applications.
Firth, James D.,Hammarback, L. Anders,Burden, Thomas J.,Eastwood, Jonathan B.,Donald, James R.,Horbaczewskyj, Chris S.,McRobie, Matthew T.,Tramaseur, Adam,Clark, Ian P.,Towrie, Michael,Robinson, Alan,Krieger, Jean-Philippe,Lynam, Jason M.,Fairlamb, Ian J. S.
supporting information
p. 3979 - 3985
(2021/02/03)

Fluorescent probe for detecting active oxygen molecule and preparation method and application thereof
The invention discloses a fluorescent probe for detecting reactive oxygen molecules and a preparation method and application thereof, wherein the fluorescent probe comprises a quinolinium ion framework. The trimethylsilyl based on carbon-silicon single bo
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Paragraph 0047-0051

(2021/10/27)

Cross-Coupling through Ag(I)/Ag(III) Redox Manifold
In ample variety of transformations, the presence of silver as an additive or co-catalyst is believed to be innocuous for the efficiency of the operating metal catalyst. Even though Ag additives are required often as coupling partners, oxidants or halide scavengers, its role as a catalytically competent species is widely neglected in cross-coupling reactions. Most likely, this is due to the erroneously assumed incapacity of Ag to undergo 2e? redox steps. Definite proof is herein provided for the required elementary steps to accomplish the oxidative trifluoromethylation of arenes through AgI/AgIII redox catalysis (i. e. CEL coupling), namely: i) easy AgI/AgIII 2e? oxidation mediated by air; ii) bpy/phen ligation to AgIII; iii) boron-to-AgIII aryl transfer; and iv) ulterior reductive elimination of benzotrifluorides from an [aryl-AgIII-CF3] fragment. More precisely, an ultimate entry and full characterization of organosilver(III) compounds [K]+[AgIII(CF3)4]? (K-1), [(bpy)AgIII(CF3)3] (2) and [(phen)AgIII(CF3)3] (3), is described. The utility of 3 in cross-coupling has been showcased unambiguously, and a large variety of arylboron compounds was trifluoromethylated via [AgIII(aryl)(CF3)3]? intermediates. This work breaks with old stereotypes and misconceptions regarding the inability of Ag to undergo cross-coupling by itself.
Demonti, Luca,Mézailles, Nicolas,Nebra, Noel,Saffon-Merceron, Nathalie
supporting information
p. 15396 - 15405
(2021/10/12)

Orthogonal Stability and Reactivity of Aryl Germanes Enables Rapid and Selective (Multi)Halogenations
While halogenation is of key importance in synthesis and radioimaging, the currently available repertoire is largely designed to introduce a single halogen per molecule. This report makes the selective introduction of several different halogens accessible. Showcased here is the privileged stability of nontoxic aryl germanes under harsh fluorination conditions (that allow selective fluorination in their presence), while displaying superior reactivity and functional-group tolerance in electrophilic iodinations and brominations, outcompeting silanes or boronic esters under rapid and additive-free conditions. Mechanistic experiments and computational studies suggest a concerted electrophilic aromatic substitution as the underlying mechanism.
Deckers, Kristina,Fricke, Christoph,Schoenebeck, Franziska
supporting information
p. 18717 - 18722
(2020/08/25)

Generation of Organozinc Reagents from Arylsulfonium Salts Using a Nickel Catalyst and Zinc Dust
Readily available aryldimethylsulfonium triflates react with zinc powder under nickel catalysis via the selective cleavage of the sp2-hybridized carbon-sulfur bond to produce salt-free arylzinc triflates under mild conditions. This zincation displays superb chemoselectivity and thus represents a protocol that is complementary or orthogonal to existing methods. The generated arylzinc reagents show both high reactivity and chemoselectivity in palladium-catalyzed and copper-mediated cross-coupling reactions.
Yamada, Kodai,Yanagi, Tomoyuki,Yorimitsu, Hideki
p. 9712 - 9718
(2021/01/09)

A synthetic approach to dimetalated arenes using flow microreactors and the switchable application to chemoselective cross-coupling reactions
In spite of their potential utility, the chemistry of dimetalated arenes is still in its infancy because they are extremely difficult to synthesize. We report a novel method of synthesizing arenes bearing a boryl group and a metallic substituent, such as boryl, silyl, stannyl, or zincyl groups, in an integrated flow microreactor based on the generation and reactions of aryllithiums bearing a trialkyl borate moiety. The bimetallic arenes showed a remarkable chemoselectivity in palladium-catalyzed cross-coupling reactions. The selectivity was switched by the selection of the metal species that constitutes the dimetalated arenes as well as appropriate catalysts.
Nagaki, Aiichiro,Ashikari, Yosuke,Kawaguchi, Tomoko,Mandai, Kyoko,Aizawa, Yoko
supporting information
p. 17039 - 17047
(2020/11/10)

Luminescent tungsten(vi) complexes as photocatalysts for light-driven C-C and C-B bond formation reactions
The realization of photocatalysis for practical synthetic application hinges on the development of inexpensive photocatalysts which can be prepared on a large scale. Herein an air-stable, visible-light-absorbing photoluminescent tungsten(vi) complex which can be conveniently prepared at the gram-scale is described. This complex could catalyse photochemical organic transformation reactions including borylation of aryl halides, such as aryl chloride, reductive coupling of benzyl bromides for C-C bond formation, reductive coupling of phenacyl bromides, and decarboxylative coupling of redox-active esters of alkyl carboxylic acid with high product yields and broad functional group tolerance.
Chan, Kaai-Tung,Che, Chi-Ming,Du, Lili,Liu, Yungen,Phillips, David Lee,To, Wai-Pong,Tong, Glenna So Ming,Wu, Liang-Liang,Yu, Daohong
p. 6370 - 6382
(2020/07/15)

Visible-Light-Photosensitized Aryl and Alkyl Decarboxylative Functionalization Reactions
Despite significant progress in aliphatic decarboxylation, an efficient and general protocol for radical aromatic decarboxylation has lagged far behind. Herein, we describe a general strategy for rapid access to both aryl and alkyl radicals by photosensitized decarboxylation of the corresponding carboxylic acids esters followed by their successive use in divergent carbon–heteroatom and carbon–carbon bond-forming reactions. Identification of a suitable activator for carboxylic acids is the key to bypass a competing single-electron-transfer mechanism and “switch on” an energy-transfer-mediated homolysis of unsymmetrical σ-bonds for a concerted fragmentation/decarboxylation process.
Patra, Tuhin,Mukherjee, Satobhisha,Ma, Jiajia,Strieth-Kalthoff, Felix,Glorius, Frank
p. 10514 - 10520
(2019/07/12)

Visible light-promoted formation of C-B and C-S bonds under metal- A nd photocatalyst-free conditions
A green, efficient, photoinduced synthesis of arylboronic esters and aryl sulfides has been developed. Bench stable arylazo sulfones were used as radical precursors for a photocatalyst- A nd additive-free carbon-heteroatom bond formation under visible light. The protocols are applicable to a wide range of substrates, providing products in good yields.
Blank, Lena,Fagnoni, Maurizio,Protti, Stefano,Rueping, Magnus
p. 1243 - 1252
(2019/02/26)

Fixing flexible arms of core-shared ligands to enhance the stability of metal-organic frameworks
In recent years, more and more research on metal-organic frameworks (MOFs) has focused on exploring their practical applications, where the stability is crucial. Besides the metal-ligand coordination bond, the configuration of the ligand also plays an imp
Dong, Chen,Bai, Jinquan,Lv, Xiu-Liang,Wu, Wei,Lv, Jie,Li, Jian-Rong
supporting information
p. 15909 - 15916
(2019/12/02)

Cleavage of C(aryl)?CH3 Bonds in the Absence of Directing Groups under Transition Metal Free Conditions
Organic chemists now can construct carbon–carbon σ-bonds selectively and sequentially, whereas methods for the selective cleavage of carbon–carbon σ-bonds, especially for unreactive hydrocarbons, remain limited. Activation by ring strain, directing groups, or in the presence of a carbonyl or a cyano group is usually required. In this work, by using a sequential strategy site-selective cleavage and borylation of C(aryl)?CH3 bonds has been developed under directing group free and transition metal free conditions. Methyl groups of various arenes are selectively cleaved and replaced by boryl groups. Mechanistic analysis suggests that it proceeds by a sequential intermolecular oxidation and coupling of a transient aryl radical, generated by radical decarboxylation, involving a pyridine-stabilized persistent boryl radical.
Dai, Peng-Fei,Ning, Xiao-Shan,Wang, Hua,Cui, Xian-Chao,Liu, Jie,Qu, Jian-Ping,Kang, Yan-Biao
supporting information
p. 5392 - 5395
(2019/03/29)

A general electrochemical strategy for the Sandmeyer reaction
Herein we report a general electrochemical strategy for the Sandmeyer reaction. Using electricity as the driving force, this protocol employs a simple and inexpensive halogen source, such as NBS, CBrCl3, CH2I2, CCl4, LiCl and NaBr for the halogenation of aryl diazonium salts. In addition, we found that these electrochemical reactions could be performed using anilines as the starting material in a one-pot fashion. Furthermore, the practicality of this process was demonstrated in the multigram scale synthesis of aryl halides using highly inexpensive graphite as the electrode. A series of detailed mechanism studies have been performed, including radical clock and radical scavenger study, cyclic voltammetry analysis and in situ electron paramagnetic resonance (EPR) analysis.
Liu, Qianyi,Sun, Beiqi,Liu, Zheng,Kao, Yi,Dong, Bo-Wei,Jiang, Shang-Da,Li, Feng,Liu, Guoquan,Yang, Yang,Mo, Fanyang
p. 8731 - 8737
(2018/12/10)

Convenient and General Zinc-Catalyzed Borylation of Aryl Diazonium Salts and Aryltriazenes under Mild Conditions
A convenient and general zinc-catalyzed borylation of aryl diazonium salts and aryltriazenes has been developed. With bis- (pinacolato)diboron as the borylation reagent, aryldiazonium tetrafluoroborate salts and aryltriazenes were transformed into the corresponding arylboronates in moderate to excellent yields under mild conditions. As a convenient and practical methodology, no additional ligands, base, or any other additives are required here.
Qi, Xinxin,Jiang, Li-Bing,Zhou, Chao,Peng, Jin-Bao,Wu, Xiao-Feng
p. 345 - 349
(2017/06/23)

Mechanochemical borylation of aryldiazonium salts; merging light and ball milling
Merging of photo- and mechanochemical activation permitted studying the role of eosin Y in the borylation of aryldiazonium salts in a ball mill. Simultaneous neat grinding/irradiation of the reactants and the photocatalyst led to the formation of boronates in a molten state. On the other hand, the catalyst-free liquid-assisted grinding/irradiation reaction also led to product formation, featuring a direct photolysis pathway facilitated by substrate–solvent charge-transfer complex formation.
Hernández, José G.
supporting information
p. 1463 - 1469
(2017/08/02)

Transition-Metal-Free, Visible-Light-Enabled Decarboxylative Borylation of Aryl N-Hydroxyphthalimide Esters
Herein, we report a conceptually novel borylation reaction proceeding via a mild photoinduced decarboxylation of redox-activated aromatic carboxylic acids. This work constitutes the first application of cheap and easily prepared N-hydroxyphthalimide esters as aryl radical precursors and does not require the use of expensive transition metals or ligands. The reaction is operationally simple, scalable, and displays broad scope and functional group tolerance.
Candish, Lisa,Teders, Michael,Glorius, Frank
supporting information
p. 7440 - 7443
(2017/06/13)

Borylation of aryldiazonium salts at room temperature in an aqueous solution under catalyst-free conditions
A general and convenient borylation reaction of aryldiazonium tetrafluoroborate salts with B2pin2 has been developed. In this catalytic system, no catalyst, additional ligands or additives were required. The reaction proceeded smoothly in an aqueous solution, and a variety of arylboronates were isolated in moderate to excellent yields under mild reaction conditions.
Qi, Xinxin,Li, Hao-Peng,Peng, Jin-Bao,Wu, Xiao-Feng
supporting information
p. 3851 - 3853
(2017/09/15)

Iridium-Catalyzed Intramolecular Methoxy C?H Addition to Carbon–Carbon Triple Bonds: Direct Synthesis of 3-Substituted Benzofurans from o-Methoxyphenylalkynes
Catalytic hydroalkylation of an alkyne with methyl ether was accomplished. Intramolecular addition of the C?H bond of a methoxy group in 1-methoxy-2-(arylethynyl)benzenes across a carbon–carbon triple bond took place efficiently either in toluene at 110 °C or in p-xylene at 135 °C in the presence of an iridium catalyst. The initial 5-exo cyclization products underwent double-bond migration during the reaction to give 3-(arylmethyl)benzofurans in high yields.
Torigoe, Takeru,Ohmura, Toshimichi,Suginome, Michinori
supporting information
p. 10415 - 10419
(2016/07/21)

Efficient synthesis of aryl boronates via zinc-catalyzed cross-coupling of alkoxy diboron reagents with aryl halides at room temperature
A zinc(II)/NHC system catalyzes the borylation of aryl halides with diboron (4) reagents in the presence of KOMe at rt. This transformation can be applied to a broad range of substrates with high functional group compatibility. Radical scavenger experiments do not support a radical-mediated process.
Bose, Shubhankar Kumar,Marder, Todd B.
supporting information
p. 4562 - 4565
(2015/01/08)

NEW PROCESS FOR PREPARING ARYLBORANES BY ARYLATION OF ORGANOBORON COMPOUNDS
The present invention relates to a new process for the preparation of an arylborane compound, by arylation of a B-H bond, which comprises a step (1) of contacting an arenediazonium salt or a heteroarenediazonium salt with an organoboron compound containing at least one B-H bond, in a reaction medium containing a solvent, in the absence of base, in the absence or in the presence of an activating agent, for the preparation of an arylborane compound, and a possible step (2) of recovery and purification of said arylborane compound obtained at the step (1), said arylborane being in particular an aminoarylborane, and a possible step (3) of refunctionalisation of said arylborane obtained at step (1) or (2) for the preparation of aryl boronic derivatives or arylborates.
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(2014/02/15)

New process for preparing arylboranes by arylation of organoboron compounds
The present invention relates to a new process for the preparation of an arylborane compound, by arylation of a B-H bond, which comprises a step (1) of contacting an arenediazonium salt or a heteroarenediazonium salt with an organoboron compound containing at least one B-H bond, in a reaction medium containing a solvent, in the absence of base, in the absence or in the presence of an activating agent, for the preparation of an arylborane compound, and a possible step (2) of recovery and purification of said arylborane compound obtained at the step (1), said arylborane being in particular an aminoarylborane, and a possible step (3) of refunctionalisation of said arylborane obtained at step (1) or (2) for the preparation of aryl boronic derivatives or arylborates.
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Paragraph 0108; 0109; 0110; 0111; 0162; 0163

(2014/01/23)

Methanol-promoted borylation of arylamines: A simple and green synthetic method to arylboronic acids and arylboronates
A Sandmeyer borylation of arylamines via a SN2Ar pathway promoted by methanol with sodium nitrite and hydrochloric acid as diazotization agent has been developed, which provide a simple and green synthetic method to arylboronic acids and arylboronates. Georg Thieme Verlag Stuttgart New York.
Zhao, Cong-Jun,Xue, Dong,Jia, Zhi-Hui,Wang, Chao,Xiao, Jianliang
supporting information
p. 1577 - 1584
(2014/07/08)

Iron-catalysed borylation of arenediazonium salts to give access to arylboron derivatives via aryl(amino)boranes at room temperature
Complementary to previously described Miyaura borylation methods, a new access to boron derivatives via aryl(amino)boranes is described. Direct coupling between aryldiazonium salts and diisopropylaminoborane is catalysed by 0.1% ferrocene leading to the formation of a carbon-boron bond. The obtained aryl(amino)boranes could eventually then be transformed into boronic acids, boronates or borates. Copyright
Marciasini, Ludovic D.,Richy, Nicolas,Vaultier, Michel,Pucheault, Mathieu
supporting information
p. 1083 - 1088
(2013/05/21)

Synthesis of pinacol arylboronates from aromatic amines: A metal-free transformation
A metal-free borylation process based on Sandmeyer-type transformation using arylamines derivatives as the substrates has been developed. Through optimization of the reaction conditions, this novel conversion can be successfully applied to a wide range of aromatic amines, affording borylation products in moderate to good yields. Various functionalized arylboronates, which are difficult to access by other methods, can be easily obtained with this metal-free transformation. Moreover, this transformation can be followed by Suzuki-Miyaura cross-coupling without purification of the borylation products, which enhances the practical usefulness of this method. A possible reaction mechanism involving radical species has been proposed.
Qiu, Di,Jin, Liang,Zheng, Zhitong,Meng, He,Mo, Fanyang,Wang, Xi,Zhang, Yan,Wang, Jianbo
p. 1923 - 1933
(2013/03/29)

Copper-mediated fluorination of arylboronate esters. Identification of a Copper(III) fluoride complex
A method for the direct conversion of arylboronate esters to aryl fluorides under mild conditions with readily available reagents is reported. Tandem reactions have also been developed for the fluorination of arenes and aryl bromides through arylboronate ester intermediates. Mechanistic studies suggest that this fluorination reaction occurs through facile oxidation of Cu(I) to Cu(III), followed by rate-limiting transmetalation of a bound arylboronate to Cu(III). Fast C-F reductive elimination is proposed to occur from an aryl-copper(III)-fluoride complex. Cu(III) intermediates have been generated independently and identified by NMR spectroscopy and ESI-MS.
Fier, Patrick S.,Luo, Jingwei,Hartwig, John F.
supporting information
p. 2552 - 2559
(2013/03/29)

Transition-metal-free borylation of aryltriazene mediated by BF 3·OEt2
A practical and simple method for deaminoborylation of aryltriazene with bis(pinacolato)diboron has been developed that is mediated by BF 3·OEt2. Various arylboronic esters are prepared in moderate to good yields with this facile transition-metal-free procedure.
Zhu, Chuan,Yamane, Motoki
p. 4560 - 4563
(2012/10/30)

A facile route to aryl boronates: Room-temperature, copper-catalyzed borylation of aryl halides with alkoxy diboron reagents
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Kleeberg, Christian,Dang, Li,Lin, Zhenyang,Marder, Todd B.
supporting information; experimental part
p. 5350 - 5354
(2009/12/01)

Development of a second generation of inhibitors of microsomal prostaglandin E synthase 1 expression bearing the γ-hydroxybutenolide scaffold
Petrosaspongiolide M (PM, 1), a marine sesterterpene metabolite bearing the γ-hydroxybutenolide scaffold and displaying a potent inhibitory activity toward PLA2 enzyme, was selected by us as an attractive target in order to explore its mechanis
Aquino, Maurizio,Guerrero, Maria D.,Bruno, Ines,Terencio, Maria C.,Paya, Miguel,Riccio, Raffaele
p. 9056 - 9064
(2008/12/23)

2-CARBOXY THIOPHENE DERIVATIVES AS ANTI-VIRAL AGENTS
Anti-viral agents of compounds of Formula (I) : wherein A, Rx, Ry, R2 and R3 are as defined in the specification, processes for their preparation and their use in HCV treatment are provided.
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Page/Page column 27

(2008/12/08)

Formation of arylboronates by a Cul-catalyzed coupling reaction of pinacolborane with aryl iodides at room temperature
The coupling reaction of pinacolborane with aryl iodides under the catalysis of 10 mol % Cul and the action of sodium hydride in THF works at room temperature to provide corresponding arylboronates in good yields. Aryl bromides give poor conversion under these reaction conditions.
Zhu, Wei,Ma, Dawei
p. 261 - 263
(2007/10/03)

Rhodium and iridium complexes of N-heterocyclic carbenes: Structural investigations and their catalytic properties in the borylation reaction
Bridged and unbridged N-heterocyclic carbene (NHC) ligands are metalated with [Ir/Rh(COD)2Cl]2 to give rhodium(I/III) and iridium(I) mono- and biscarbene substituted complexes. All complexes were characterized by spectroscopy, in addition [Ir(COD)(NHC)2][Cl,I] [COD = 1,5-cyclooctadiene, NHC = 1,3-dimethyl- or 1,3-dicyclohexylimidazolin-2-ylidene] (1, 4), and the biscarbene chelate complexes 12 [(η4-1,5-cyclooctadiene)(1,1′-di-n-butyl-3,3′-ethylene-diimidazolin-2,2′-diylidene)iridium(I) bromide] and 14 [(η4-1,5-cyclooctadiene)(1,1′-dimethyl-3,3′-o-xylylene-diimidazolin-2,2′-diylidene)iridium(I) bromide] were characterized by single crystal X-ray analysis. The relative σ-donor/π-acceptor qualities of various NHC ligands were examined and classified in monosubstituted NHC-Rh and NHC-Ir dicarbonyl complexes by means of IR spectroscopy. For the first time, bis(carbene) substituted iridium complexes were used as catalysts in the synthesis of arylboronic acids starting from pinacolborane and arene derivatives.
Frey, Guido D.,Rentzsch, Christoph F.,von Preysing, Denise,Scherg, Tobias,Mühlhofer, Michael,Herdtweck, Eberhardt,Herrmann, Wolfgang A.
p. 5725 - 5738
(2007/10/03)

The synthesis and characterization of phenylacetylene tripodal compounds containing boroxine cores
A convergent synthesis of phenylacetylene tripodal compounds containing boroxine cores has been accomplished. The boroxine cores are assembled in high yield either by chemical dehydration or ligand-facilitated trimerization of the corresponding monomeric
Perttu, Emily K.,Arnold, Matthew,Iovine, Peter M.
p. 8753 - 8756
(2007/10/03)

Preparation and selective reactions of mixed bimetallic aromatic and heteroaromatic boron-magnesium reagents
(Chemical Equation Presented) It's all in the mix: The magnesiation of iodoaryl and iodoheteroaryl boronic esters with iPrMgCl·LiCl leads to mixed bimetallic compounds, which react with a variety of electrophiles to provide highly functionalized boronic e
Baron, Oliver,Knochel, Paul
p. 3133 - 3135
(2007/10/03)

Palladium-catalyzed borylation of aryldiazonium tetrafluoroborate salts. A new synthesis of arylboronic esters
The first synthesis of arylboronic esters via the coupling of bis(pinacolato)diboron with easily prepared aryldiazonium tetrafluoroborate salts is reported. The palladium-catalyzed borylation reaction proceeds efficiently under mild reaction conditions in the absence of a base to afford various functionalized arylboronic esters in moderate to high yields. (C) 2000 Elsevier Science Ltd.
Willis,Strongin
p. 8683 - 8686
(2007/10/03)