20740-05-0Relevant articles and documents
Nickel-catalyzed cross-coupling of sterically hindered 1-bromomethyl-o-carborane with alkyl and aryl Grignard reagents
Lu, Juyou,Wan, Hong,Xue, Yunna,Du, Yongmei,Lu, Jian
, p. 7842 - 7846 (2015)
A convenient and efficient Ni-catalyzed reaction has been developed for synthesis of mono-substituted o-carboranes, involving cross-coupling of readily available and sterically hindered 1-bromomethyl-o-carborane with various alkyl and aryl Grignard reagents under mild conditions, and the corresponding o-carborane derivatives were obtained in good to excellent yields. This method should provide a new strategy for construction of diverse and useful functionalized boron cluster compounds for medicinal chemistry and material chemistry.
Polyborane reactions in ionic liquids: New efficient routes to functionalized decaborane and o-carborane clusters
Kusari, Upal,Li, Yuqi,Bradley, Mark G.,Sneddon, Larry G.
, p. 8662 - 8663 (2004)
In contrast to reactions that have been observed in traditional organic solvents, decaborane olefin-hydroboration and alkyne-insertion reactions have been found to proceed in ionic liquid solvents without the need of a catalyst. These reactions now provide important new, high-yield synthetic pathways to functionalized decaborane and o-carborane clusters. Copyright
Palladium-catalyzed regioselective synthesis of B(4,5)-or B(4)-substituted: O-carboranes containing α,β-unsaturated carbonyls
Li, Jiaoyi,Lu, Jian,Tian, Song,Wang, Qian,Zhang, Chuyi,Zhang, Jianwei,Zhou, Ling
supporting information, p. 4723 - 4727 (2020/07/13)
With the help of a carboxylic acid directing group, Pd-catalyzed regioselective synthesis of B(4,5)-or B(4)-substituted o-carboranes containing α,β-unsaturated carbonyls has been reported. The-COOH, removed during the course of the reaction, is responsible for controlling the regioselectivity. The desired products could be obtained in moderate to good yields.
Copper-catalyzed cross-coupling of 1-haloalkyl-o-carboranes with Grignard reagents: An efficient route to monosubstituted o-carborane derivatives
Lu, Ju-You,Du, Yongmei,Zhao, Bo,Lu, Jian
supporting information, p. 161 - 169 (2015/12/23)
A convenient and efficient copper-catalyzed reaction has been developed for the synthesis of functionalized o-carborane derivatives by using a Cu/phosphine catalytic system. Cross-coupling of readily available 1-haloalkyl-o-carboranes with Grignard reagents proceeds efficiently under mild conditions, and the corresponding monosubstituted o-carboranes were obtained in good to excellent yields.
Straightforward synthesis of radioiodinated Cc-substituted o-carboranes: Towards a versatile platform to enable the in vivo assessment of BNCT drug candidates
Gona,Thota,Baz,Gómez-Vallejo,Llop
, p. 9915 - 9920 (2015/06/08)
Due to their high boron content and rich chemistry, dicarba-closo-dodecaboranes (carboranes) are promising building blocks for the development of drug candidates with application in Boron Neutron Capture Therapy. However, the non-invasive determination of their pharmacokinetic properties to predict therapeutic efficacy is still a challenge. Herein, we have reported the unprecedented preparation of mono-[125I] iodinated decaborane via a catalyst-assisted isotopic exchange. Subsequent reactions of the radiolabelled species with acetylenes in acetonitrile under microwave heating yield the corresponding 125I-labelled, Cc-substituted o-carboranes with good overall radiochemical yields in short reaction times. The same synthetic strategy was successfully applied to the preparation of 131I-labelled analogues, and further extension to other radioisotopes of iodine such as 124I (positron emitter) or 123I (gamma emitter) can be envisaged. Hence, the general strategy reported here is suitable for the preparation of a wide range of radiolabelled Cc-substituted o-carborane derivatives. The labelled compounds might be subsequently investigated in vivo by using nuclear imaging techniques such as Single Photon Emission Computerized Tomography or Positron Emission Tomography.
Ionic-liquid-promoted decaborane dehydrogenative alkyne-insertion reactions: A new route to o-carboranes
Li, Yuqi,Carroll, Patrick J.,Sneddon, Larry G.
, p. 9193 - 9202 (2009/03/12)
Unlike in conventional organic solvents, where Lewis base catalysts are required, decaborane dehydrogenative alkyne-insertion reactions proceed rapidly in biphasic ionic-liquid/toluene mixtures with a wide variety of terminal and internal alkynes, thus providing efficient, one-step routes to functional o-carborane 1-R-1,2-C2B10H11 and 1-R-2-R′-1,2-C2B10H10 derivatives, including R = C6H5- (1), C6H13- (2), HC≡C-(CH2)5- (3), (1-C2B 10H11)-(CH2)5-(4), CH 3CH2C(O)OCH2- (5), (C2H 5)2NCH2- (6), NC-(CH2)3- (7), 3-HC≡C-C6H4- (8), (1-C2B 10H11)-1,3-C6H4-(9), HC≡C-CH2-O-CH2- (10); R,R′ = C 2H5- (11); R = HOCH2-, R′ = CH 3- (12); R = BrCH2-; R′ = CH3- (13); R = H2C=C(CH3)-, R′ = C2H5- (14). The best results were obtained from reactions with only catalytic amounts of bmimCl (1-butyl-3-methylimidazolium chloride), where in many cases reaction times of less than 20 min were required. The experimental data for these reactions, the results observed for the reactions of B10H 13- salts with alkynes, and the computational studies reported in the third paper in this series all support a reaction sequence involving (1) the initial ionic liquid promoted formation of the B 10H13- anion, (2) addition of B 10H13- to the alkyne to form an arachno-R,R′-C2B10H13- anion, and (3) protonation of arachno-R,R′-C2B10H 13- to form the final neutral 1-R-2-R′-1,2-C 2B10H10 product with loss of hydrogen.
