886362-11-4Relevant academic research and scientific papers
Metal-free oxidative decarbonylative coupling of aromatic aldehydes with arenes: Direct access to biaryls
Tang, Ren-Jin,He, Qing,Yang, Luo
supporting information, p. 5925 - 5928 (2015/03/30)
A metal-free oxidative decarbonylative coupling of aromatic aldehydes with electron-rich or electron-deficient arenes to produce biaryl compounds was developed. This novel coupling was proposed to proceed via a non-chain radical homolytic aromatic substitution (HAS) type mechanism, based on the substrate scope, ortho-regioselectivity, radical trapping experiments and DFT calculation studies. With the ready availability of aromatic aldehydes and arenes, metal-free conditions should make this coupling attractive for the biaryl synthesis.
Synthesis of aryl trimethylstannanes from aryl amines: A sandmeyer-type stannylation reaction
Qiu, Di,Meng, He,Jin, Liang,Wang, Shuai,Tang, Shengbo,Wang, Xi,Mo, Fanyang,Zhang, Yan,Wang, Jianbo
supporting information, p. 11581 - 11584 (2013/11/06)
Sandmeyer-type stannylation: Stille coupling is one of the most powerful coupling reactions for C-C bond formation, whereas there are only limited methods to access aryl stannane compounds. A mild stannylation process based on a Sandmeyer-type transformation using aromatic amines as the starting materials is described. DCE: 1,2-dichloroethane. Copyright
Practical synthesis of pinacolborane for one-pot synthesis of unsymmetrical biaryls via aromatic C-H borylation-cross-coupling sequence
Kikuchi, Takao,Nobuta, Yusuke,Umeda, Junko,Yamamoto, Yasunori,Ishiyama, Tatsuo,Miyaura, Norio
, p. 4967 - 4971 (2008/09/21)
A method for practical preparation of pinacolborane from borane-diethylaniline and pinacol was newly developed. Aromatic C-H borylation of arenes with pinacolborane or bis(pinacolato)diboron catalyzed by 1/2[Ir(OMe)(COD)]2-(4,4′-di-tert-butyl-2,2′-bipyridine) at 25 °C in hexane to give arylboronic esters was directly followed by cross-coupling with aromatic bromides at 60 °C in the presence of PdCl2(dppf) (3.0 mol %) and K3PO4 in DMF. This one-pot, two-step procedure provided a variety of unsymmetrical biaryls in high yields.
