51317-51-2Relevant academic research and scientific papers
Radical Anion Promoted Chemoselective Cleavage of Csp2-S Bond Enables Formal Cross-Coupling of Aryl Methyl Sulfones with Alcohols
Bai, Jixiang,Wang, Tianxin,Dai, Botao,Liu, Qingchao,Yu, Peiyuan,Jia, Tiezheng
supporting information, p. 5761 - 5765 (2021/08/16)
A novel formal cross-coupling of aryl methyl sulfones and alcohols affording alkyl aryl ethers via an SRN1 pathway is developed. Two marketed antitubercular drugs were efficiently prepared employing this approach as the key step. A dimsyl-anion initiated radical chain process was revealed as the major pathway. DFT calculations indicate that the formation of a radical anion via nucleophilic addition of alkoxide to the aryl radical is the key step in determining the observed chemoselectivity.
Ullmann C[sbnd]O coupling of sterically hindered secondary alcohols using excess amount of strongly coordinating monodentate ligands
Sugata, Hayato,Tsubogo, Tetsu,Kino, Yoshitaka,Uchiro, Hiromi
supporting information, p. 1015 - 1019 (2017/02/18)
A new effective copper catalyzed C[sbnd]O coupling reaction using excess amount of strongly coordinating monodentate ligands was successfully developed. Among the DMAP-type monodentate ligands, 4-pyrrolidinopyridine afforded the best results. The developed reaction is widely applicable for the synthesis of various hindered or acyclic secondary alkyl-aryl ethers. In this study, a novel and remarkable acceleration of the coupling reaction using excess amount of monodentate ligands was discovered.
Alkylation of phenol by β-pinene in the presence of aluminum phenolate
Chukicheva,Shumova,Kuchin
experimental part, p. 43 - 46 (2012/07/17)
The alkylation of phenol by β-pinene using Al(OPh)3 as a catalyst was studied. It was found that the composition of the products depended on the ratio of starting materials. The principal products were chromane-type ethers with an equimolar ratio of starting materials and an excess of phenol. ortho-Alkylated phenol and an ether with a terpene substituent of bornyl structure were formed with a two-fold excess of β-pinene.
Tandem molecular rearrangement in the alkylation of phenol with camphene
Chukicheva,Spirikhin,Kuchin
, p. 62 - 66 (2008/12/21)
The alkylation of phenol with camphene in the presence of boron trifluoride in glacial acetic acid was accompanied by tandem molecular rearrangement with formation of a mixture of ortho- and para-substituted phenols having 1,7,7-trimethylbicyclo[2.2.1]hept-exo-2-yl and 5,5,6-trimethylbicyclo[2.2.1] hept-exo-2-yl substituents. The same products were obtained by rearrangement of 1,7,7-trimethylbicyclo[2.2.1]hept-exo-2-yloxybenzene under analogous conditions. Similar reactions performed in the presence of aluminum phenoxide as catalyst resulted in predominant formation of the corresponding ortho-substituted phenols.
Alkylation of phenol and its derivatives with camphene on large-porous β-zeolite
Fomenko,Korchagina,Salakhutdinov,Bagryanskaya,Gatilov,Ione,Barkhash
, p. 539 - 552 (2007/10/03)
Alkylation of phenol, anisole, and their methyl-substituted derivative with camphene catalyzed by large-porous β-zeolite yielded the corresponding terpenylphenols, terpenylanisoles, and terpenyl phenyl ethers. C- or O-alkylation occurs depending on phenol
TERPENOIDS. CONDENSATION PRODUCTS OF LONGIFOLENE AND PHENOL
PATNEKAR SG,BHATTACHARYYA SC
, p. 36 - 39 (2007/10/13)
The condensation of longifolene with phenol in the presence of BF//3-etherate at 0 C affords a mixture of two longibornyl phenyl ethers, the structures of which and also of the isobornyl phenyl ether, obtained by a similar reaction from camphene, have been established by their stereospecific cleavage to the known alcohols with li-liquid ammonia. The condensation of longifolene with phenol at 100 C leads to the formation of terpenyl phenois of undecided structures.
