7515-24-4Relevant articles and documents
Organocatalytic trans Phosphinoboration of Internal Alkynes
Fritzemeier, Russell G.,Nekvinda, Jan,Rosenblum, Carol Ann,Santos, Webster L.,Slebodnick, Carla,Vogels, Christopher M.,Westcott, Stephen A.
supporting information, p. 14358 - 14362 (2020/07/04)
We report the first trans phosphinoboration of internal alkynes. With an organophosphine catalyst, alkynoate esters and the phosphinoboronate Ph2P-Bpin are efficiently converted into the corresponding trans-α-phosphino-β-boryl acrylate products in moderate to good yield with high regio- and Z-selectivity. This reaction operates under mild conditions and demonstrates good atom economy, requiring only a modest excess of the phosphinoboronate. X-ray crystallography experiments allowed structural assignment of the unprecedented and densely functionalized (Z)-α-phosphino-β-boryl acrylate products.
Efficient Access to Chiral β-Borylated Carboxylic Esters via Rh-Catalyzed Hydrogenation
Liu, Gang,Li, Anqi,Qin, Xueyuan,Han, Zhengyu,Dong, Xiu-Qin,Zhang, Xumu
, p. 2844 - 2848 (2019/04/26)
Rh/bisphosphine?thiourea ligand (ZhaoPhos)-catalyzed asymmetric hydrogenation of (Z)-β-substituted-β-boryl-α,β-unsaturated esters was successfully developed, furnishing a variety of chiral β-borylated carboxylic esters with high yields and excellent enantioselectivities (up to 99% yield and >99% ee). The gram-scale asymmetric hydrogenation was performed efficiently in the presence of only 0.05 mol% (S/C=2 000) catalyst loading with full conversion, 99% yield and 99% ee. Moreover, the hydrogenation product was easily converted to other versatile synthetic intermediates, such as methyl (S)-3-hydroxy-3-phenylpropanoate and methyl (S)-3-(furan-2-yl)-3-phenylpropanoate. (Figure presented.).
Palladium-Catalyzed Ylidyl-Carbonylation of Aryl Halides to Produce α-Acylphosphoranes
Guo, Xiaojun,Ma, Wei,Xue, Dong,Wang, Chao,Xiao, Jianliang
supporting information, p. 4824 - 4827 (2016/10/14)
An efficient synthesis of α-acylphosphoranes by palladium-catalyzed carbonylation of aryl iodides with carbon monoxide and stabilized phosphonium ylides has been developed. Featuring 44 examples, the protocol displayed a wide substrate scope under mild reaction conditions, showcasing its potential in synthetic organic chemistry.
