118513-79-4Relevant academic research and scientific papers
Substituent Directed Phototransformations of BN-Heterocycles: Elimination vs Isomerization via Selective B-C Bond Cleavage
Yang, Deng-Tao,Mellerup, Soren K.,Peng, Jin-Bao,Wang, Xiang,Li, Quan-Song,Wang, Suning
, p. 11513 - 11516 (2016)
Electron-rich and -poor BN-heterocycles with benzyl-pyridyl backbones and two bulky aryls on the boron (Ar = tipp, BN-1, Ar = MesF, BN-2) have been found to display distinct molecular transformations upon irradiation by UV light. BN-1 undergoes an efficient photoelimination reaction forming a BN-phenanthrene with PE = 0.25, whereas BN-2 undergoes a thermally reversible, stereoselective, and quantitative isomerization to a dark colored BN-1,3,5-cyclooctatriene (BN-1,3,5-COT, BN-2a). This unusual photoisomerization persists for other BN-heterocycles with electron-deficient aryls such as BN-3 with a benzyl-benzothiazolyl backbone and MesF substituents or BN-4 with a benzyl-pyridyl backbone and two C6F5 groups on the boron. The photoisomerization of BN-4 goes beyond BN-1,3,5-COT (BN-4a), forming a new species (BN-1,3,6-COT, BN-4b) via C-F bond cleavage and [1,3]-F atom sigmatropic migration. Computational studies support that BN-4a is an intermediate in the formation of BN-4b. This work establishes that steric and electronic factors can effectively control the transformations of BN-heterocycles, allowing access to important and previously unknown BN-embedded species.
Bonding in Barium Boryloxides, Siloxides, Phenoxides and Silazides: A Comparison with the Lighter Alkaline Earths
Carpentier, Jean-Fran?ois,Cordier, Marie,Dorcet, Vincent,Hammoud, Joanna,Kahlal, Samia,Le Coz, Erwann,Roisnel, Thierry,Saillard, Jean-Yves,Sarazin, Yann
supporting information, p. 11966 - 11982 (2021/07/16)
Barium complexes ligated by bulky boryloxides [OBR2]? (where R=CH(SiMe3)2, 2,4,6-iPr3-C6H2 or 2,4,6-(CF3)3-C6H2), siloxide
Traceless Protection for More Broadly Applicable Olefin Metathesis
Mu, Yucheng,Nguyen, Thach T.,van der Mei, Farid W.,Schrock, Richard R.,Hoveyda, Amir H.
supporting information, p. 5365 - 5370 (2019/03/21)
An operationally simple in situ protection/deprotection strategy that significantly expands the scope of kinetically controlled catalytic Z- and E-selective olefin metathesis is introduced. Prior to the addition of a sensitive Mo- or Ru-based complex, treatment of a hydroxy- or a carboxylic-acid-containing olefin with commercially available HB(pin) or readily accessible HB(trip)2 (pin=pinacolato, trip=2,4,6-tri(isopropyl)phenyl) for 15 min is sufficient for efficient generation of a desired product. Routine workup leads to quantitative deprotection. A range of stereochemically defined Z- and E-alkenyl chlorides, bromides, fluorides, and boronates or Z-trifluoromethyl-substituted alkenes with a hydroxy or carboxylic acid group were thus prepared in 51–97 % yield with 93 to >98 % stereoselectivity. We also show that, regardless of whether a polar functional unit is present or not, a small amount of HB(pin) may be used to remove residual water, significantly enhancing efficiency.
Hindered Organoboron Groups in Organic Chemistry. Part 22. Some Interesting Properties of 2,4,6-Triisopropylphenylborane (Tripylborane, TripBH2, A New Useful Monoarylborane
Smith, Keith,Pelter, Andrew,Jin, Zhao
, p. 395 - 396 (2007/10/02)
2,4,6-Triisopropylphenylborane (tripylborane, TripBH2) is a solid, stable, hydroborating agent that hydroborates monosubstituted alkenes to give either TripBHR1 or TripBR12.TripBHR1 can be converted into mixed boranes TripBR1R2 (R1,R2 = primary alkyl, Rp) and TripBRpRs and TripBRs2 are also readily available.Oxidation of these products gives the corresponding alcohols in excellent yields, with a high selectivity for alkan-1-ols in the cases of groups derived from alk-1-enes.Cyanidation of TripBR2 proceeds to give ketones without migration of the aryl group.This establishes the low migratory aptitude of the aryl group and also that no scrambling of alkyl groups occurs.The tripyl group of TripBRp2 can be selectively removed.
