16002-93-0Relevant academic research and scientific papers
Saturation transfer and chemical exchange measurements of the stereochemical drift occurring during the Wittig reaction
Pascariu, Aurelia,Mracec, Mircea,Berger, Stefan
, p. 451 - 456 (2005)
The Wittig reaction of butylidenetriphenylphosphorane with benzaldehyde using LiHMDS as base in THF was studied. The stereochemical drift (different ratio obtained in alkenes versus oxaphosphetane intermediates) was followed by low-temperature 1D NMR tech
Effect of substituents on the thermal decomposition of diazirines: Experimental and computational studies
Liu, Michael T. H.,Choe, Yoong-Kee,Kimura, Masahiro,Kobayashi, Kaoru,Nagase, Shigeru,Wakahara, Takatsugu,Niino, Yasuyuki,Ishitsuka, Midori O.,Maeda, Yutaka,Akasaka, Takeshi
, p. 7471 - 7478 (2003)
The thermal decomposition of phenylchlorodiazirine (1), phenyl-n-butyldiazirine (2), and 2-adamantane-2,3′-[3H]diazirine (3) has been studied in solution in the presence of C60. The C60 probe technique indicates that in the decomposition diazirine 1 yielded exclusively phenylchlorocarbene, diazirine 2 yielded mainly a diazo intermediate, and diazirine 3 yielded a mixture of carbene and diazo compound. In the case of diazirine 2, 13percent of (E)-1-phenyl-1-pentene resulted from the direct thermal rearrangement of diazirine without the participation of a carbene. As well, the thermal decomposition of these diazirines has been studied theoretically with ab initio and density functional methods. The experimental results are broadly in agreement with the theoretical predictions. The calculations further indicate that the rebound reaction between carbene and molecular nitrogen leading to the formation of a diazo intermediate is an important reaction in the gas-phase decomposition of diazirine.
Synthesis of Functionalized Heteroaromatics: Application to Formal Total Synthesis of Camptothecin
Murata, Naoko,Sugihara, Takumichi,Kondo, Yoshinori,Sakamoto, Takao
, p. 298 - 300 (1997)
The formal total synthesis of camptothecin was achieved via two types of lithiation reactions of pyridine derivatives and a Pd-catalyzed carbonylation of pyridylmethyl methanesulfonates.
Pd-catalyzed coupling reaction of allyl and propargyl ethers with chlorosilanes
Naitoh, Yoshitaka,Bando, Fumiaki,Terao, Jun,Otsuki, Kazutaka,Kuniyasu, Hitoshi,Kambe, Nobuaki
, p. 236 - 237 (2007)
Pd-catalyzed synthesis of allylsilanes from chlorosilanes and allyl ethers is described. The reaction proceeds efficiently at room temperature by the use of phenyl or vinyl Grignard reagent in the presence of palladium catalysts. The present method can also be applied to synthesis of propargylsilanes by the use of propargyl ethers. Copyright
Solventless Suzuki coupling reactions on palladium-doped KF/Al2O3
Kabalka, George W.,Pagni, Richard M.,Hair, C. Maxwell
, p. 1423 - 1425 (1999)
(equation presented) A solventless Suzuki coupling has been developed. A commercially available potassium fluoride-alumina mixture is utilized along with palladium black.
Unexpected 1,5-dilithiation of chiral o-TMS blocked (dimethylamino) phenylmethylferrocene: An alternative approach to chiral ferrocenyl 1,5-diphosphanes
Fukuzawa, Shin-Ichi,Yamamoto, Masahisa,Kikuchi, Satoshi
, p. 1514 - 1517 (2007)
(Chemical Equation Presented) The 1,5-dilithiation of o-TMS blocked (dimethylamino)phenylmethylferrocene 4 unexpectedly occurred even though one equimolar amount of t-BuLi was used and the 1,5-dilithiated ferrocene 6 was trapped by iodine followed by remo
Enantioselective copper-catalyzed SN2' substitution with Grignard reagents
Alexakis,Malan,Lea,Benhaim,Fournioux
, p. 927 - 930 (2001)
Cinnamyl chlorides undergo selective SN2' allylic substitution by Grignard reagents using catalytic amount (1 mol%) of CuCN and 1-2 mol% trivalent phosphorus ligand, in dichloromethane. With chiral phosphorus ligands derived from TADDOL ee's up
METHODS OF BORYLATION AND USES THEREOF
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Page/Page column 63, (2021/04/30)
The present invention relates, in general terms, to methods of borylation and uses thereof. In particular, the present invention provides a method of borylating an alkene compound by contacting the compound with a boron compound, a Fe pre-catalyst and a protic additive. The borylation occurs at a vicinal (β) position to an electron donating or electron withdrawing moiety of the compound.
Electro-mediated PhotoRedox Catalysis for Selective C(sp3)–O Cleavages of Phosphinated Alcohols to Carbanions
Barham, Joshua P.,K?nig, Burkhard,Karl, Tobias A.,Reiter, Sebastian,Tian, Xianhai,Yakubov, Shahboz,de Vivie-Riedle, Regina
supporting information, p. 20817 - 20825 (2021/08/18)
We report a novel example of electro-mediated photoredox catalysis (e-PRC) in the reductive cleavage of C(sp3)?O bonds of phosphinated alcohols to alkyl carbanions. As well as deoxygenations, olefinations are reported which are E-selective and can be made Z-selective in a tandem reduction/photosensitization process where both steps are photoelectrochemically promoted. Spectroscopy, computation, and catalyst structural variations reveal that our new naphthalene monoimide-type catalyst allows for an intimate dispersive precomplexation of its radical anion form with the phosphinate substrate, facilitating a reactivity-determining C(sp3)?O cleavage. Surprisingly and in contrast to previously reported photoexcited radical anion chemistries, our conditions tolerate aryl chlorides/bromides and do not give rise to Birch-type reductions.
Ready approach to poly(vinyldiphenylphosphine): A novel soluble polymer for conveniently conducting Wittig reactions
Ye, Jing-Jing,Han, Li-Biao
supporting information, (2021/01/25)
The novel poly(vinyldiphenylphosphine) could be easily prepared by using the reactions of the cheap poly(vinyl chloride) with sodium phosphides. Poly(vinyldiphenylphosphine) is soluble in common solvents while its corresponding phosphine oxide is hardly soluble in the solvents. Taking advantage of this different solubility, poly(vinyldiphenylphosphine) could be used as a soluble phosphinopolymer for the Wittig reactions. The reactions could take place efficiently to produce the corresponding olefins while the isolation of the products were simple since the resulted poly(vinyldiphenylphosphine oxide) was not soluble in the solvent and could be easily removed by filtration.
