Fluorination of B10H102- with an N-Fluoro Reagent. A New Way To Transform B−H Bonds into B−F Bonds

Ivanov, S. V.; Ivanova, Svetlana; Miller, Susie M.; Anderson, Oren P.; Солнцев, К. А.; Strauss, Steven H.

doi:10.1021/ic961043c

Cited by 47 publications

(14 citation statements)

References 8 publications

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“…Complex {[(MeCN) 3 Ag](Ag[2-B 10 H 9 F])} 2 was prepared by the treatment of (Ph 4 P) 2 [2-B 10 H 9 F] with silver trifluoroacetate in 9:1 dichloromethane-toluene solution followed by crystallization from acetonitrile. The structure of the {[(MeCN) 3 [32]. There is no interaction between the fluorine substituent in boron cage and either silver cation ( Figure 10) [14].…”

Section: Scheme 1 Anionic Polyhedral Boron Hydrides Discussed In Thimentioning

confidence: 99%

Silver and Copper Complexes with closo-Polyhedral Borane, Carborane and Metallacarborane Anions: Synthesis and X-ray Structure

et al. 2016

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Section: Scheme 1 Anionic Polyhedral Boron Hydrides Discussed In Thimentioning

confidence: 99%

Silver and Copper Complexes with closo-Polyhedral Borane, Carborane and Metallacarborane Anions: Synthesis and X-ray Structure

et al. 2016

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“…This stoichiometry was used to ensure that the reaction did not substitute chlorine or multiple iodine atoms on the closo -borate(2-) moiety, and to distinguish the product from starting material (which had 50% remaining) by HPLC. Both of the closo -borate(2-) moieties are known to add multiple halogen atoms to the same molecule (27) and are reactive with all of the electrophilic halogen species (28, 29). Yields of the iodinated products were measured by HPLC (ELSD detection), and in each case were approximately 50% due to limited quantities of iodination reagent used 2.…”

Section: Resultsmentioning

confidence: 99%

Reagents for Astatination of Biomolecules. 3. Comparison ofcloso-Decaborate(2-) andcloso-Dodecaborate(2-) Moieties as Reactive Groups for Labeling with Astatine-211

et al. 2009

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In vivo deastatination has been a major problem in the development of reagents for therapeutic applications of the α-particle emitting radionuclide 211 At. Our prior studies demonstrated that the use of a closo-decaborate(2-) ([closo-B 10 H 9 R] 2− ) moiety for 211 At labeling of biomolecules provides conjugates that are stable to in vivo deastatination. In this investigation, the closo-decaborate(2-) moiety was compared with the structurally similar closo-dodecaborate(2-) ([closo-B 12 H 11 R] 2− ) to determine if one has more favorable properties than the other for use in pendant groups as 211 At labeling molecules. To determine the differences, two sets of structurally identical molecules, with the exception that they contained either a closo-decaborate(2-) or a closo-dodecaborate(2-) moiety, were compared with regards to their synthesis, radiohalogenation, stability to in vivo deastatination and tissue distribution. Quite different rates of reaction were noted in the synthetic steps for the two closo-borate(2-) moieties, but ultimately the yields were similar, making these differences of little importance. Differences in radiohalogenation rates were also noted between the two closo-borate(2-) moieties, with the more electrophilic closo-decaborate(2-) reacting more rapidly. This resulted in somewhat higher yields of astatinated closo-decaborate(2-) derivatives (84% vs 53%), but both cage moieties gave good radioiodination yields (e.g. 79-96%). Importantly, both closo-borate(2-) cage moieties were shown to have high stability to in vivo deastatination. The largest differences between pairs of compounds containing the structurally similar boron cage moieties were in their in vivo tissue distributions. I]1b, was evaluated, the route of excretion appeared to be hepatobiliary rather than renal. Identical biotin derivatives containing the two closo-borate(2-) cage moieties had similar tissue distributions, except the closo-decaborate(2-) derivative had lower concentrations in kidney (1h, 19.9%ID/g; 4h, 24.4%ID/g vs. 1h, 38.9%ID/g; 4h, 40.6%ID/g). In summary, the higher reactivity, faster tissue clearance, and lower kidney concentrations make the closo-decaborate(2-) more favorable for further studies using them in reactive groups for 211 At labeling of biomolecules.

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“…2, 4 To date, fluorinated derivatives are unknown,2 which is not surprising, because [B 11 H 11 ] 2− and its derivatives exhibit a significantly lower chemical stability than [B 10 H 10 ] 2− , [B 12 H 12 ] 2− , and related species 2. The fluorination of [B 10 H 10 ] 2− is also difficult; HF is not an appropriate fluorination reagent, because the borate anion is sensitive to acids 5. Salts of a perfluorinated derivative are only known for the most stable closo ‐borate dianion, [B 12 H 12 ] 2− 6.…”

Section: Methodsmentioning

confidence: 99%

Impact of lymphadenectomy on survival in surgery for sporadic gastrinoma (Br J Surg 2012; 99: 1234–1240)

Triponez

2012

British Journal of Surgery

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Fluorination of B₁₀H₁₀²^- with an N-Fluoro Reagent. A New Way To Transform B−H Bonds into B−F Bonds

Cited by 47 publications

References 8 publications

Silver and Copper Complexes with closo-Polyhedral Borane, Carborane and Metallacarborane Anions: Synthesis and X-ray Structure

Silver and Copper Complexes with closo-Polyhedral Borane, Carborane and Metallacarborane Anions: Synthesis and X-ray Structure

Reagents for Astatination of Biomolecules. 3. Comparison ofcloso-Decaborate(2-) andcloso-Dodecaborate(2-) Moieties as Reactive Groups for Labeling with Astatine-211

Impact of lymphadenectomy on survival in surgery for sporadic gastrinoma (Br J Surg 2012; 99: 1234–1240)

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