133039-10-8Relevant articles and documents
Cross-coupling reaction of allylic ethers with aryl Grignard reagents catalyzed by a nickel pincer complex
Hashimoto, Toru,Funatsu, Kei,Ohtani, Atsufumi,Asano, Erika,Yamaguchi, Yoshitaka
, (2019/07/10)
A cross-coupling reaction of allylic aryl ethers with arylmagnesium reagents was investigated using β-aminoketonato- and β-diketiminato-based pincer-type nickel(II) complexes as catalysts. An β-aminoketonato nickel(II) complex bearing a diphenylphosphino group as a third donor effectively catalyzed the reaction to afford the target cross-coupled products, allylbenzene derivatives, in high yield. The regioselective reaction of a variety of substituted cinnamyl ethers proceeded to give the corresponding linear products. In contrast, α- and γ-alkyl substituted allylic ethers afforded a mixture of the linear and branched products. These results indicated that the coupling reaction proceeded via a π-allyl nickel intermediate.
Palladium-catalyzed allylic arylation of allylic ethers with arylboronic acids using hydrazone ligands
Mino, Takashi,Kogure, Taketo,Abe, Taichi,Koizumi, Tomoko,Fujita, Tsutomu,Sakamoto, Masami
, p. 1501 - 1505 (2013/05/09)
Unsymmetrical 1,3-diarylpropenes were synthesized in good to high yields by the palladium-catalyzed allylic arylation of allylic ethers, such as a cinnamyl phenyl ether, with a variety of arylboronic acids using a hydrazone 1a-Pd(OAc)2 system in DMAc/H2O. Using this catalyst, eugenol was also synthesized from allyl phenyl ether with (4-hydroxy-3- methoxyphenyl)boronic acid pinacol ester. A palladium-catalyzed allylic arylation of cinnamyl phenyl ether derivatives with a variety of arylboronic acids using 5 mol-% of a hydrazone 1a-Pd(OAc)2 system in DMAc/H 2O at 50 °C gave 1,3-diarylpropenes in good yields. We also succeeded with the synthesis of eugenol by a palladium-catalyzed allylic arylation. Copyright
Homogeneous silver(I) salts and heterogeneous Ag3PW 12O40-catalyzed intermolecular allylation of arenes with allylic alcohols
Chen, Guo-Qiang,Xu, Zhen-Jiang,Chan, Sharon Lai-Fung,Zhou, Cong-Ying,Che, Chi-Ming
supporting information; experimental part, p. 2713 - 2718 (2011/12/04)
AgOTf is an effective catalyst for intermolecular allylation of aromatic and heteroaromatic compounds with allylic alcohols affording allylated arenes in up to 99% yields. Heterogeneous allylation of arenes catalyzed by Ag 3PW12O40 gave comparable product yields to those obtained by AgOTf. Ag3PW12O40 could be reused five times with slightly decreased activity. Georg Thieme Verlag Stuttgart · New York.