119367-98-5Relevant academic research and scientific papers
Direct Arylation of Benzyl Ethers with Organozinc Reagents
Peng, Zhihua,Wang, Yilei,Yu, Zhi,Zhao, Dezhi,Song, Linhua,Jiang, Cuiyu
, p. 7900 - 7906 (2018/06/22)
A novel C(sp3)-H bond arylation of benzyl ethers with Knochel-type arylzinc reagents has been developed. This transition-metal-catalyst-free reaction proceeds well under mild conditions in a simple and effective manner and enables the synthesis of a wide range of potentially biologically active benzyl ethers by using highly functionalized organozinc reagents as a carbon nucleophile.
Efficient C(sp3)-H bond functionalization of isochroman by azadol catalysis
Muramatsu, Wataru,Nakano, Kimihiro
supporting information, p. 1549 - 1552 (2015/03/30)
A novel organocatalytic C(sp3)-H bond functionalization of isochroman under practical conditions has been developed. In the presence of 5.0 mol % of AZADOL, the catalysis proceeded successfully with a broad range of substrates and nucleophiles in excellent yields.
Organocatalytic approach for C(sp3)-H bond arylation, alkylation, and amidation of isochromans under facile conditions
Muramatsu, Wataru,Nakano, Kimihiro
supporting information, p. 2042 - 2045 (2014/05/06)
A new catalytic approach for the synthesis of isochroman derivatives via direct C(sp3)-H bond arylation is described. The oxidation reaction with [bis(trifluoroacetoxy)iodo]benzene facilitates the regeneration of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in the C(sp3)-H bond arylation of isochroman. The reaction conditions can also be used for alkyl Grignard reagents and amides to afford the corresponding isochroman derivatives.
Simple and direct sp3 C-H bond arylation of tetrahydroisoquinolines and isochromans via 2,3-dichloro-5,6-dicyano-1,4- benzoquinone oxidation under mild conditions
Muramatsu, Wataru,Nakano, Kimihiro,Li, Chao-Jun
supporting information, p. 3650 - 3653 (2013/08/23)
The 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated sp3 C-H bond arylation of tetrahydroisoquinolines and isochromans is described. The corresponding products were facilely synthesized via a simple nucleophilic addition reaction betwee
Intramolecular Generation of Oxonium Ylides from Functionalized Arylcarbenes
Kirmse, Wolfgang,Kund, Klaus
, p. 1465 - 1473 (2007/10/02)
Arylcarbenes carrying alkoxyalkyl groups in the ortho position have been generated by flash pyrolysis and photolysis of appropriate tosylhydrazone sodium salts.In the gas phase and in a aprotic solvents, interaction of the carbenes with the lone electron pairs of oxygen competes efficiently with insertion into C-H bonds.Both five- and six-membered cyclic oxonium ylides have been generated.The ylides 23, 37, 61b, and 74 undergo 1,2 shifts of benzyl groups with ease, even if ring contraction to highly strained benzocyclobutenes is involved (23, 74).The oxonium ylides37 and 61b strongly prefer the nonconcerted Stevens rearrangement to the sigmatropic Sommelet rearrangement, in contrast to analogous ammonium ylides.Alkyl shifts occur to a very minor extent, if at all.Evidence is presented that alcohols intercept both the carbenes and the oxonium ylides.Protonation of the ylides leads to cyclic oxonium ions, which undergo nucleophilic cleavage of the C-O bonds.Acid catalyzed decomposition of the appropriate diazo compounds gives rise to six-membered, but not to five-membered, cyclic oxonium ions, thus confirming the different intramolecular reactivities of arylcarbenes and benzyl cations.The efficiency of carbene interception increases with increasing acidity of the medium, suggesting nucleophilic behavior (protonation) of the arylcarbenes.
