1032400-18-2Relevant articles and documents
The drastic effect of cobalt and chromium catalysts in the borylation of arylzinc reagents
Komeyama, Kimihiro,Kiguchi, Shinnosuke,Takaki, Ken
, p. 7009 - 7012 (2016)
A new synthetic approach to arylboronic esters from arylzinc reagents with boryl electrophiles MeOB(OR)2 has been developed. Furthermore, this protocol could be applied to the cyclization/borylation of alkynylaryl iodides to afford cyclized vinylboronic esters.
Sequential Ni-catalyzed borylation and cross-coupling of aryl halides via in situ prepared neopentylglycolborane
Rosen, Brad M.,Huang, Chenghong,Percec, Virgil
, p. 2597 - 2600 (2008)
(Chemical Equation Presented) A procedure for NiCl2(dppp)- catalyzed pinacolborylation and neopentylglycolborylation that utilizes in situ prepared inexpensive pinacolborane and neopentylglycolborane is reported. The scope of this reaction was demonstrated with a variety of aryl bromides and iodides. The resulting aryl neopentylglycolboronic esters undergo a NiCl 2(dppe)-catalyzed cross-coupling with aryl halides, resulting in an extremely efficient and cost-effective method for the synthesis of functional biaryls, dendritic building blocks, and other complex architectures.
An Accelerated Modular-Orthogonal Ni-Catalyzed Methodology to Symmetric and Nonsymmetric Constitutional Isomeric AB2to AB9Dendrons Exhibiting Unprecedented Self-Organizing Principles
Daud, Hina,Hoffman, David J.,Huang, Ning,Jezorek, Ryan L.,Malineni, Jagadeesh,McClure, Emily R.,Partridge, Benjamin E.,Percec, Virgil,Peterca, Mihai,Sahoo, Dipankar,Song, Se Lin,Sung, Paul D.,Wang, Shitao,Wang, Xuefeng,Zhang, Na
supporting information, p. 17724 - 17743 (2021/11/04)
Five libraries of natural and synthetic phenolic acids containing five AB3, ten constitutional isomeric AB2, one AB4, and one AB5 were previously synthesized and reported by our laboratory in 5 to 11 steps. They were employed to construct seven libraries of self-assembling dendrons, by divergent generational, deconstruction, and combined approaches, enabling the discovery of a diversity of supramolecular assemblies including Frank-Kasper phases, soft quasicrystals, and complex helical organizations, some undergoing deracemization in the crystal state. However, higher substitution patterns within a single dendron were not accessible. Here we report three libraries consisting of 30 symmetric and nonsymmetric constitutional isomeric phenolic acids with unprecedented sequenced patterns, including two AB2, three AB3, eight AB4, five AB5, six AB6, three AB7, two AB8, and one AB9 synthesized by accelerated modular-orthogonal Ni-catalyzed borylation and cross-coupling. A single etherification step with 4-(n-dodecyloxy)benzyl chloride transformed all these phenolic acids, of interest also for other applications, into self-assembling dendrons. Despite this synthetic simplicity, they led to a diversity of unprecedented self-organizing principles: lamellar structures of interest for biological membrane mimics, helical columnar assemblies from rigid-solid angle dendrons forming Tobacco Mosaic Virus-like assemblies, columnar organizations from adaptable-solid angle dendrons forming disordered micellar-like nonhelical columns, columns from supramolecular spheres, five body-centered cubic phases displaying supramolecular orientational memory, rarely encountered in previous libraries forming predominantly Frank-Kasper phases, and two Frank-Kasper phases. Lessons from these self-organizing principles, discovered within a single generation of self-assembling dendrons, may help elaborate design principles for complex helical and nonhelical organizations of synthetic and biological matter.
Borylation of organo halides and triflates using tetrakis(dimethylamino) diboron
Bello, Charles S.,Schmidt-Leithoff, Joachim
, p. 6230 - 6235,6 (2012/12/11)
We report a new in situ borylation method using tetrakis(dimethylamino) diboron, DMA4B2, in the presence of a diol. Our method uses standard borylation conditions and readily available Pd-catalysts. The scope of this method includes aryl halides and triflates as well as vinyl halides and triflates. The method successfully works with a broad range of diols, enabling the selection of the best boronic ester for subsequent Suzuki coupling.
Neopentylglycolborylation of aryl mesylates and tosylates catalyzed by Ni-based mixed-ligand systems activated with Zn
Wilson, Daniela A.,Wilson, Christopher J.,Moldoveanu, Costel,Resmerita, Ana-Maria,Corcoran, Patrick,Hoang, Lisa M.,Rosen, Brad M.,Percec, Virgil
supporting information; experimental part, p. 1800 - 1801 (2010/04/24)
(Chemical Presented) The mixed-ligand system NiCl2(dppp)/dppf is shown to be an effective catalyst for the neopentylglycolborylation of ortho-, meta-, and para-substituted electron-rich and electrondeficient aryl mesylates and tosylates. The ad
Zero-valent metals accelerate the neopentylglycolborylation of aryl halides catalyzed by NiCl2-based mixed-ligand systems
Leowanawat, Pawaret,Resmerita, Ana-Maria,Moldoveanu, Costel,Liu, Chi,Zhang, Na,Wilson, Daniela A.,Hoang, Lisa M.,Rosen, Brad M.,Percec, Virgil
supporting information; experimental part, p. 7822 - 7828 (2011/02/22)
The highly active mixed-ligand catalytic system NiCl2(dppp)/dppf combined with the reducing effect of zerovalent Zn and of other metals was used to demonstrate a method for the dramatic acceleration of the rate and for the enhancement of the yi
PROCESSES FOR THE PREPARATION OF BIPHENYL COMPOUNDS
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Page/Page column 17, (2010/01/29)
The invention concerns processes for the synthesis of a compound of the formula: wherein: R1 and R2 are each, independently, C1-C12 alkyl, CO2R3, OR4, R5(OR6), or C6-C18 aiyl; R3 -R6 are each, independently, C1-C12 alkyl or C6-C12 aryl; and n and m are each, independently, O or an integer from 1-5; said process comprising: — contacting a compound of the formula H0-R7-0H with BH3 and a compound of the formula in the presence of a nickel-containing catalyst to produce a first product, where R7 is a C2-C12 hydrocarbon group and X is a halogen, OMs or OTs; — contacting the first product in situ with a compound of the formula: in the presence of a nickel-containing catalyst to produce a compound of formula I, where Z is a halogen.
Neopentylglycolborylation of aryl chlorides catalyzed by the mixed ligand system NiCl2(dppp)/dppf
Moldoveanu, Costel,Wilson, Daniela A.,Wilson, Christopher J.,Corcoran, Patrick,Rosen, Brad M.,Percec, Virgil
supporting information; experimental part, p. 4974 - 4977 (2010/01/16)
The mixed ligand system 10 mol % NICl2(dppp) with 5 mol % dppf was discovered to be an extremely efficient catalyst for the neopentylglycolborylation of a diversity of electron-rich and electron-deficient aryl chlorides. Optimization showed tha
