324753-14-2Relevant articles and documents
Reduction of Tertiary Phosphine Oxides by BH 3 Assisted by Neighboring Activating Groups
Sowa, Sylwia,Stankevi?, Marek,Flis, Anna,Pietrusiewicz, K. Micha?
, p. 2106 - 2118 (2018/02/28)
Tertiary sulfanylphosphine and aminoalkylphosphine oxides can be easily converted into the corresponding tertiary sulfanylphosphine- and aminoalkylphosphine-boranes, respectively, through the facile P=O bond reduction by borane complexes. The easy reduction of the strong P=O bond by BH 3, a mild reducing agent, has been achieved through an intramolecular P=O - B complexation directed by proximal SH or NH activating groups located at the α- or β-position to the P=O bond. A generalized reduction mechanism has been proposed.
A Photo-Triggered Traceless Staudinger–Bertozzi Ligation Reaction
Hu, Peng,Feng, Tianshi,Yeung, Chi-Chung,Koo, Chi-Kin,Lau, Kai-Chung,Lam, Michael H. W.
, p. 11537 - 11542 (2016/08/05)
The use of light to control the course of a chemical/biochemical reaction is an attractive idea because of its ease of administration with high precision and fine spatial resolution. Staudinger ligation is one of the commonly adopted conjugation processes that involve a spontaneous reaction between azides and arylphosphines to form iminophosphoranes, which further hydrolyze to give stable amides. We designed an anthracenylmethyl diphenylphosphinothioester (1) that showed promising Staudinger ligation reactivity upon photo-excitation. Broadband photolysis at 360–400 nm in aqueous organic solvents induced heterolytic cleavage of its anthracenylmethyl–phosphorus bond, releasing a diphenylphosphinothioester (2) as an efficient traceless Staudinger–Bertozzi ligation reagent. The quantum yield of such a photo-induced heterolytic bond-cleavage at the optimal wavelength of photolysis (376 nm) at room temperature is ≥0.07. This work demonstrated the feasibility of photocaging arylphosphines to realize the photo-triggering of the Staudinger ligation reaction.
High-yielding staudinger ligation of a phosphinothioester and azide to form a peptide
Nilsson, Bradley L.,Kiessling, Laura L.,Raines, Ronald T.
, p. 9 - 12 (2007/10/03)
(eqution presented) The Staudinger ligation can be used to couple a peptide with a C-terminal phosphinothioester to another with an N-terminal α-azido group to form a single peptide that contains no residual atoms. Here, diphenylphosphinomethanethiol thio
