580-13-2Relevant articles and documents
Direct bromodeboronation of arylboronic acids with CuBr2 in water
Tang, Yan-Ling,Xia, Xian-Song,Gao, Jin-Chun,Li, Min-Xin,Mao, Ze-Wei
supporting information, (2021/01/05)
An efficient and practical method has been developed for the preparation of aryl bromides via the direct bromodeboronation of arylboronic acids with CuBr2 in water. This strategy provides several advantages, such as being ligand-free, base-free, high yielding, and functional group tolerant.
ipso-Bromination/iodination of arylboronic acids: Poly(4-vinylpyridine)-Br2/I2 complexes as safe and efficient reagents
Fu, Fang,Gurung, Laxman,Czaun, Miklos,Mathew, Thomas,Prakash, G.K. Surya
supporting information, (2019/08/26)
Poly(4-vinyl pyridine) supported bromine/iodine complexes were prepared and probed for ipso-bromination/iodination of arylboronic acids. These solid complexes with catalytic amount of additive are found to be safe and efficient reagent system for the ipso-bromination/iodination. The reaction occurs under mild conditions and tolerates various functional groups resulting in products with high selectivity and yields.
Acceptorless Dehydrogenation of Hydrocarbons by Noble-Metal-Free Hybrid Catalyst System
Fuse, Hiromu,Kojima, Masahiro,Mitsunuma, Harunobu,Kanai, Motomu
supporting information, p. 2042 - 2045 (2018/04/16)
A hybrid catalysis that comprises an acridinium photoredox catalyst, a thiophosphate organocatalyst, and a nickel catalyst-enabled acceptorless dehydrogenation of hydrocarbons is reported. The cationic nickel complex played a critical role in the reactivity. This is the first example of acceptorless dehydrogenation of hydrocarbons by base metal catalysis under mild reaction conditions of visible light irradiation at room temperature.
Nickel-Catalyzed Deamidative Step-Down Reduction of Amides to Aromatic Hydrocarbons
Dey, Aniruddha,Sasmal, Sheuli,Seth, Kapileswar,Lahiri, Goutam Kumar,Maiti, Debabrata
, p. 433 - 437 (2017/06/05)
To date, cleavage of the C-N bond in aromatic amides has been achieved in molecules with a distorted constitutional framework around the nitrogen atom. In this report, a nickel-catalyzed reduction of planar amides to the corresponding lower hydrocarbon homologue has been reported. This involves a one-pot reductive cleavage of the C-N bond followed by a tandem C-CO bond break in the presence of a hydride source. Substrate scope circumscribes deamidation examples which proceed via oxidative addition of nickel in the amide bonds of nontwisted amides. Mechanistic studies involving isolation and characterization of involved intermediates via different spectroscopic techniques reveal a deeper introspection into the plausible catalytic cycle for the methodology.
A mild and ligand-free Ni-catalyzed silylation via C-OMe cleavage
Zarate, Cayetana,Nakajima, Masaki,Martin, Ruben
, p. 1191 - 1197 (2017/05/16)
Metal-catalyzed transformations that forge carbon-heteroatom bonds are of central importance in organic synthesis. Despite the formidable potential of aryl methyl ethers as coupling partners, the scarcity of metal-catalyzed C-heteroatom bond formations via C-OMe cleavage is striking, with isolated precedents requiring specialized, yet expensive, ligands, high temperatures, and π-extended backbones. We report an unprecedented catalytic ipso-silylation of aryl methyl ethers under mild conditions and without recourse to external ligands. The method is distinguished by its wide scope, which includes the use of benzyl methyl ethers, vinyl methyl ethers, and unbiased anisóle derivatives, thus representing a significant step forward for designing new C-heteroatom bond formations via C-OMe scission. Applications of this transformation in orthogonal silylation techniques as well as in further derivatizations are also described. Preliminary mechanistic experiments suggest the intermediacy of Ni(0)-ate complexes, leaving some doubt that a canonical catalytic cycle consisting of an initial oxidative addition of the C-OMe bond to Ni(0) species comes into play.
A mild Ni/Cu-catalyzed silylation via C -O cleavage
Zarate, Cayetana,Martin, Ruben
, p. 2236 - 2239 (2014/03/21)
A Ni/Cu-catalyzed silylation of unactivated C-O electrophiles derived from phenols or benzyl alcohols is described. This transformation is characterized by its wide scope and mild conditions, providing a direct access to synthetically versatile silylated compounds. The protocol allows for the coupling of C(sp 2)-O and even C(sp3)-O bonds with similar efficiency.
Halodeboronation of organotrifluoroborates using tetrabutylammonium tribromide or cesium triiodide
Yao, Min-Liang,Kabalka, George W.,Blevins, David W.,Reddy, Marepally Srinivasa,Yong, Li
experimental part, p. 3738 - 3743 (2012/06/30)
Halodeboronation of organotrifluoroborates using commercially available tetrabutylammonium tribromide (TBATB) or cesium triiodide in aqueous medium is reported. The mild, transition metal-free method has proven to be tolerant of a wide range of functional groups. High regio- and chemoselectivity are observed. Two synthetic routes to (Z)-dibromoalkenes from alkynes, through stereodefined (Z)-2-bromoalkenyltrifluoroborates and (Z)-1,2-bis(boryl) alkenyltrifluoroborates, have been developed using the TBATB mediated bromodeboronation as the key step.
Ruthenium-catalyzed transformation of aryl and alkenyl triflates to halides
Imazaki, Yusuke,Shirakawa, Eiji,Ueno, Ryota,Hayashi, Tamio
supporting information, p. 14760 - 14763 (2012/11/07)
Aryl triflates were transformed to aryl bromides/iodides simply by treating them with LiBr/NaI and [Cp*Ru(MeCN)3]OTf. The ruthenium complex also catalyzed the transformation of alkenyl sulfonates and phosphates to alkenyl halides under mild conditions. Aryl and alkenyl triflates undergo oxidative addition to a ruthenium(II) complex to form η'1- arylruthenium and 1-ruthenacyclopropene intermediates, respectively, which are transformed to the corresponding halides.
An improved palladium-catalyzed conversion of aryl and vinyl triflates to bromides and chlorides
Pan, Jun,Wang, Xinyan,Zhang, Yong,Buchwald, Stephen L.
supporting information; experimental part, p. 4974 - 4976 (2011/11/06)
A facile Pd-catalyzed conversion of aryl and vinyl triflates to aryl and vinyl halides (bromides and chlorides) is described. This method allows convenient access to a variety of aryl, heteroaryl, and vinyl halides in good to excellent yields and with greatly simplified conditions relative to our previous report.
Chemoselective bromodeboronation of organotrifluoroborates using tetrabutylammonium tribromide: Application in (Z)-dibromoalkene syntheses
Yao, Min-Liang,Reddy, Marepally Srinivasa,Li, Yong,Walfish, Ingrid,Blevins, David W.,Kabalka, George W.
supporting information; experimental part, p. 700 - 703 (2010/04/02)
(Chemical Equation Presented) Tetrabutylammonlum trlbromlde (TBATB) has been found to be a unique bromodeboronatlon reagent for organotrlf luoroborates. When compared to previously reported bromodeboronatlon methods, the mild and metal-free reaction conditions tolerate a wider range of functional groups. High reglo- and chemoselectlvlty are observed In the presence of both unsaturated carbon-carbon bonds and aldehyde functional groups. An efficient synthetic route to (Z)-dlbromoalkenes from terminal alkynes has been developed using the TBATB-medlated bromodeboronatlon as a key step.
