317832-05-6Relevant articles and documents
Rh(III)-Catalyzed Phosphine Oxide Migration Reactions: Selective Synthesis of 3-Phosphinoylindoles
Wang, Chun-Hai,Yang, Shang-Dong
, p. 2401 - 2404 (2018/09/10)
3-Phosphinoylindoles are important components of biological active natural products and materials in pharmaceuticals. Herein, a new approach for the synthesis of 3-phosphinoylindoles has been established by a Rh(III)-catalyzed cyclization from readily acc
Metal-free electrophilic phosphination of electron-rich arenes, arenols and aromatic thiols with diarylphosphine oxides
Yuan, Tao,Huang, Shenlin,Cai, Chun,Lu, Guo-Ping
supporting information, p. 30 - 33 (2017/12/27)
A new protocol for achieving the phosphination of arenes, arenols and thiols has been disclosed. This chemistry, in which diaryl(((trifluoromethyl)sulfonyl)oxy)phosphines as a kind of electrophilic phosphination reagents are in situ generated from diarylp
Regioselective Direct C3-Phosphorylation of N-Sulfonylindoles under Mild Oxidative Conditions
Su, Feng,Lin, Weidong,Zhu, Pengfei,He, Dezhi,Lin, Jianbin,Zhang, Hui-Jun,Wen, Ting-Bin
supporting information, p. 947 - 951 (2017/03/27)
The reactions of N-sulfonylindoles with H-phosphine oxides under oxidative conditions give a wide range of C-3 phosphorylated free (NH)-indoles. Several mild oxidants, such as AgNO3, di-tert-butyl peroxide (DTBP), and K2S2O8, can be used to promote this transformation. (Figure presented.).
3,3'-bis(diphenylphosphino)-1,1'-disubstituted-2,2'-biindoles: Easily accessible, electron-rich, chiral diphosphine ligands for homogeneous enantioselective hydrogenation of oxoesters
Benincori,Piccolo,Rizzo,Sannicolo
, p. 8340 - 8347 (2007/10/03)
Racemic (±)-3,3'-bis(diphenylphosphinyl)-1,1'-dimethyl-2,2'-biindole (1c) (N-Me-2-BINPO) and (±)-3,3'-bis(diphenylphosphinyl)-1,1'-bis(methoxymethyl)-2,2'-biindole (1d) (N-MOM-2-BINPO) were synthesized in satisfactory yields following a three-step reaction sequence, starting from indole. Resolution of racemic 1c and 1d was achieved through fractional crystallization of their diastereomeric adducts with optically active dibenzoyl tartaric acids, followed by alkaline decomplexation of the diastereomerically pure salts. Their trichlorosilane reduction gave enantiopure phosphines (+)- and (-)-(1a) (N-Me-2-BINP) and (+)- and (-)-(1b) (N-MOM-2-BINP). The electrochemical oxidative potential of 1a and 1b was found to be 0.52 and 0.60 V, respectively. Both the enantiomers of (1a) were tested as ligands of Ru(II) in asymmetric hydrogenation reactions of α- and β-oxoesters. Reactions were found to be outstandingly fast and enantioselection quite good. Comparative kinetic experiments on the hydrogenation reaction of methyl acetoacetate carried out with 1a, 1c, BINAP, and other biheteroaromatic diphosphines as ligands of Ru(II) demonstrated that all the reactions follow a first-order kinetic. A linear relationship was found between the kinetic constant log and the electrochemical oxidative potential of the diphosphine ligand.
